KR102667150B1 - Manufacturing method of organic compound - Google Patents

Abstract

This specification provides a method for producing organic compounds.

Description

{MANUFACTURING METHOD OF ORGANIC COMPOUND}

This specification relates to a method for producing organic compounds.

Conventionally, a deposition process has been mainly used to manufacture organic light-emitting devices. However, when manufacturing an organic light emitting device through a deposition process, there is a problem that a lot of material loss occurs. To solve this problem, a technology for manufacturing devices through a solution process that can increase production efficiency by reducing material loss and Materials used in organic light-emitting devices for solution processing are being developed.

However, in the synthesis of existing solution process materials, a cryogenic process is performed, a solvent corresponding to a specially controlled substance such as DMF (dimehthylformamide) is used, or purification using a column is used to synthesize solution process materials. There are problems in that it is difficult to handle the manufacturing process for mass production and that it is difficult to scale up the factory for mass production. In addition, there is a problem in that the purification yield is low and the process time is long in the process of synthesizing the material, making it uneconomical. .

Therefore, a new manufacturing method is required to solve these problems.

Korean Patent Publication No. 10-2015-0066429

Some embodiments of the present specification are intended to provide methods for producing organic compounds that can be applied to mass production.

In addition, some embodiments of the present specification provide a method for producing organic compounds with improved yield and reduced solvent usage and process time during purification.

One embodiment of this specification is

A first step of reacting a compound of Formula 1 below with a compound of Formula 2 below to obtain a first product; and

It provides a method for producing an organic compound comprising a second step of introducing a thermosetting group or a photocurable group in place of H of the OH group of the first product.

[Formula 1]

[Formula 2]

In Formulas 1 and 2,

Ar1 to Ar3 are the same or different from each other and are substituted or unsubstituted aryl groups,

L is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

X1 is a halogen group.

According to another embodiment of the present specification, the second step is

A third step of obtaining a second product by reacting the first product with a compound having a thermosetting group or a photocurable group containing a ketone group; and

The ketone group of the second product is converted to an alkene group. and a fourth step of obtaining a third product having a thermosetting group or a photocuring group.

According to another embodiment of the present specification, the first step further includes purifying the first product by recrystallization.

According to another embodiment of the present specification, the second step further includes purifying the organic compound by recrystallization.

According to another embodiment of the present specification, the third step further includes purifying the second product by recrystallization.

According to another embodiment of the present specification, the fourth step further includes purifying the third product by recrystallization.

The method for producing an organic compound of the present invention is a method of producing a compound having a structure in which two fluorene structures having a thermosetting group or a photocuring group are connected using a diamine as a linking group, and the starting materials and reaction sequence are consistent with the embodiments of the present specification. By specifying the same, a solvent that does not require special management can be used as a solvent and can be applied to mass production, and the purification process can also use a recrystallization process rather than a column process, greatly reducing the amount of solvent usage and process time. The yield of the compound can also be improved.

Figure 1 is a diagram showing a mass measurement graph of Compound 1.

Hereinafter, the present invention will be described in detail.

In this specification, the term “substitution” means changing the hydrogen atom bonded to the carbon atom of the compound to another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, When two or more substituents are substituted, the two or more substituents may be the same or different from each other.

As used herein, the term “substituted or unsubstituted” refers to hydrogen; heavy hydrogen; halogen group; Nitrile group; nitro group; hydroxyl group; Alkyl group; Alkoxy group; alkenyl group; Aryl group; and substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group, or substituted or unsubstituted with two or more substituents among the above-exemplified substituents linked. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, “thermocurable group or photocurable group” may mean a reactive substituent that crosslinks compounds by exposing them to heat and/or light. Crosslinking can be created by heat treatment or light irradiation, where radicals generated when carbon-carbon multiple bonds and cyclic structures are decomposed are connected.

According to one embodiment of the present specification,

A first step of reacting a compound of Formula 1 below with a compound of Formula 2 below to obtain a first product; and

It provides a method for producing an organic compound comprising a second step of introducing a thermosetting group or a photocurable group in place of H of the OH group of the first product.

[Formula 1]

[Formula 2]

In Formulas 1 and 2,

Ar1 to Ar3 are the same or different from each other and are substituted or unsubstituted aryl groups,

L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group,

X1 is a halogen group.

[Step 1]

The first step is a step of reacting the compound of Formula 1 with the compound of Formula 2.

According to one example, in Formula 1, X1 is a halogen group.

According to one example, in Formula 1, X1 is F, Cl, Br, or I.

According to one example, in Formula 1, X1 is Br.

According to one example, in Formula 1, Ar1 is a C6 to C20 aryl group substituted or unsubstituted with an alkyl group.

According to one example, in Formula 1, Ar1 is a C6 to C20 aryl group substituted with a straight-chain or branched alkyl group.

According to one example, in Formula 1, Ar1 is a C6 to C12 aryl group substituted with a C3 to C12 branched alkyl group.

According to one example, in Formula 1, Ar1 is a phenyl group substituted with t-butyl.

According to one example, in Formula 2, Ar2 and Ar3 are the same or different from each other and are C6 to C20 aryl groups.

According to one example, Ar2 and Ar3 in Formula 2 are the same or different from each other and are a phenyl group, biphenylyl group, terphenylyl group, or naphthyl group.

According to one example, in Formula 2, Ar2 and Ar3 are phenyl groups.

According to one example, in Formula 2, L is a C6 to C30 arylene group or a C2 to C30 heteroarylene group.

According to one example, in Formula 2, L is a phenylene group, biphenylylene group, terphenylylene group, or naphthylene group.

According to one example, Chemical Formula 1 may be expressed as Chemical Formula 1-1 below.

[Formula 1-1]

In Formula 1-1, the definition of the substituent is the same as the definition in Formula 1.

The compound of Formula 1 and the compound of Formula 2 can theoretically react at a molar ratio of 2:1, but if necessary, they can be reacted at a molar ratio of 30:10 to 9:10, preferably 21:10 to 20:10. can be used

According to one embodiment, in the first step, the compound of Formula 1 and the compound of Formula 2 may be reacted in a solvent.

Toluene may be used as the solvent, but is not limited thereto.

According to another embodiment, the solvent may be xylene, mesitylene, benzene, methylbenzene, ethylbenzene, or isopropylbenzene, but is not limited thereto.

The amount of solvent used may be determined depending on the solubility or reaction conditions of the compound of Formula 1 and the compound of Formula 2. For example, the compound of Formula 1 may be used in an amount of 30 g to 600 g, preferably 50 g to 300 g, per 1 L of solvent. The compound of Formula 2 can be used in an amount of 5 g to 150 g, preferably 10 g to 100 g, per 1 L of solvent.

According to one embodiment, in the first step, a base such as K ₂ CO ₃ , CsCO ₃ , KOAc, preferably potassium t-butoxide or sodium t-butoxide, more preferably sodium t-butoxide. may be further used, but is not limited thereto.

According to another embodiment, in the first step, a Pd-containing catalyst may be further used. Pd-containing catalysts include, but are not limited to, Pd(t-Bu ₃ P) ₂ , Pd(dba) ₂ , Pd(PPh ₃ ) ₄ , Pd(dppp)Cl ₂ or Pd(dppf)Cl ₂ .

According to one example, in the first step, Pd(t-Bu ₃ P) ₂ may be further used as a Pd-containing catalyst.

The amount of catalyst used may be determined depending on the amount of the compound of Formula 1 and the compound of Formula 2. For example, it can be used at an amount of 0.01 to 1.0 compared to the compound of Formula 1. If the above range is exceeded, economic loss occurs due to unnecessary catalyst use, and if a small amount is used than the above range, there is a problem in that the synthesis yield is lowered.

According to one embodiment, the first step is preferably carried out in an inert atmosphere, for example, it may be carried out under a nitrogen atmosphere.

According to one embodiment, the first step may be performed at 50°C to 120°C, preferably 60°C to 100°C, and more preferably 75°C to 90°C. When the above range is satisfied, there is an advantage in that the highest yield can be obtained.

The reaction time in the first step may be determined depending on reaction conditions such as the type or amount of starting material, the type or amount of solvent, and reaction temperature, and may be carried out for, for example, 30 minutes to 3 hours, but is not limited thereto. .

When the reaction in the first step is completed, the temperature is lowered to room temperature and the reaction is terminated. To terminate the reaction, for example water can be added.

After the reaction is completed, the first product prepared in the first step can be separated. The step of separating the first product may, for example, phase-separate the organic layer, dry residual moisture, and remove the organic solvent. Drying of residual moisture can be performed using MgSO ₄ (Magnesium sulfate). Removal of the organic solvent can be done using a method known in the art, for example, using a vacuum rotary concentrator.

The first product prepared in the first step may be represented by the following formula (3).

[Formula 3]

In Formula 3, the definitions of Ar1, Ar2, Ar3, and L are the same as those in Formulas 1 and 2, and Ar1' is the same as or different from Ar1 to Ar3 and is a substituted or unsubstituted aryl group.

According to one example, Chemical Formula 3 may be expressed as Chemical Formula 3-1 below.

[Formula 3-1]

In Formula 3-1, the definitions of Ar1, Ar1', Ar2, Ar3, and L are the same as those in Formula 3.

According to another embodiment of the present specification, the first step further includes purifying the first product by recrystallization.

In this specification, the recrystallization process refers to a process of dissolving a desired solute using a difference in solubility and then crystallizing it again.

In this specification, refining refers to a process performed to increase the purity of a compound.

Recrystallization of the first product may be performed by first dissolving the first product using a first solvent and then crystallizing the first product using a second solvent. DMSO can be used as the first solvent, and a mixture of water and ethanol in a volume ratio of 1:3.5 can be used as the second solvent. Additionally, the second solvent may be an alcohol such as methanol or 2-propanol, but is not limited thereto.

[Second stage]

According to another embodiment of the present specification, the second step is

A third step of obtaining a second product by reacting the first product with a compound having a thermosetting group or a photocurable group containing a ketone group; and

It includes a fourth step of obtaining a third product having a thermosetting group or a photocurable group in which the ketone group of the second product is converted to an alkene group.

[Step 3]

According to one example, in the third step, the compound having a thermosetting group or a photocuring group including the ketone group may be represented by the following formula (4).

[Formula 4]

In Formula 4, X2 is a halogen group or a nitro group, and is preferably a fluorine group.

According to one example, Chemical Formula 4 may be expressed as Chemical Formula 4-1 below.

[Formula 4-1]

In Formula 4-1, the definition of X2 is the same as that in Formula 4.

According to one example, X2 is F, Cl, Br, I or _NO2 .

The OH group of the first product and the halogen group or nitro group of the compound can theoretically react at a 1:1 molar ratio, but if necessary, the molar ratio is 1:1 to 1:6, preferably 1:2 to 1:5. It can be used at a molar ratio of If the range is satisfied, there is an advantage in that the product can be obtained with the highest purity.

The solvent in the third step may be DMSO or the like, but is not limited thereto.

The amount of solvent used may be determined depending on the solubility of the first product or reaction conditions. For example, the first product may be used in an amount of 30 g to 300 g, preferably 50 g to 150 g, per 1 L of solvent.

According to another embodiment, in the third step, a base such as K ₂ CO ₃ , CsCO ₃ , KOAc, potassium t-butoxide or sodium t-butoxide, preferably K ₂ CO ₃ or CsCO ₃ , More preferably, K ₂ CO ₃ can be used, but it is not limited thereto.

According to one embodiment, the third step may be performed at 50°C to 120°C, preferably 60°C to 100°C, and more preferably 75°C to 95°C. When the above temperature range is satisfied, there is an advantage in that the highest yield can be obtained.

The reaction time in the third step may be determined depending on reaction conditions such as the type or amount of starting material, the type or amount of solvent, and reaction temperature, and may be carried out for, for example, 30 minutes to 10 hours, but is not limited thereto. .

When the reaction in the third step is completed, the temperature is lowered to room temperature and the reaction is terminated. To terminate the reaction, for example water can be added.

After the reaction is completed, the second product prepared in the third step can be separated. The step of separating the second product may include, for example, filtering the produced solid, washing and drying if necessary. Water can be used for the washing, and drying can be performed in a vacuum oven at 60°C to 100°C.

The second product prepared in the third step may be represented by the following formula (5).

[Formula 5]

In Formula 5, the definitions of substituents are the same as those in Formulas 1 to 3.

According to one example, Chemical Formula 5 may be expressed as Chemical Formula 5-1 below.

[Formula 5-1]

In Formula 5-1, the definitions of substituents are the same as those in Formulas 1 to 3.

According to another embodiment of the present specification, the third step further includes purifying the second product by recrystallization. The recrystallization may be performed by first dissolving the second product using a third solvent and then crystallizing the second product using a fourth solvent. DMSO can be used as the third solvent, and 2-propanol can be used as the fourth solvent.

[Step 4]

According to one embodiment, the fourth step can be performed by contacting methyltriphenylphosphonium bromide with the second product.

The molar ratio of the compounds is second product:methyltriphenylphosphonium bromide = 1:1 to 1:2.5, preferably 1:2. If the range is used below, starting materials remain and the conversion rate decreases. If the range is exceeded, there is a disadvantage in reducing economic efficiency due to the use of unnecessary reactants. However, if the range is satisfied, maximum synthetic purity can be obtained.

According to another embodiment, in the fourth step, K ₂ CO ₃ , CsCO ₃ , KOAc, a base such as potassium t-butoxide or sodium t-butoxide, preferably a strong base, potassium t-butoxide. Side or sodium t-butoxide, more preferably potassium t-butoxide, can be used, but it is not limited thereto.

According to one embodiment, a solvent may be used in the fourth step. THF or the like may be used as a solvent in the fourth step. At this time, methyl tertiary butyl ether (MTBE) or toluene can be used instead of THF.

The amount of solvent used may be determined depending on the solubility of the second product or reaction conditions. For example, the second product may be used in an amount of 50 g to 600 g, preferably 100 g to 300 g, per 1 L of solvent.

According to one embodiment, the fourth step may be performed at -10°C to 15°C, preferably -5°C to 5°C. The fourth step is preferably carried out in an inert atmosphere, for example, it can be carried out under a nitrogen atmosphere. When the above range is satisfied, there is an advantage in that the highest yield can be obtained.

According to one example, the fourth step may be performed by mixing methyltriphenylphosphonium bromide and potassium t-butoxide with a solvent, and then adding the mixture of the second product and the solvent dropwise thereto. Additional stirring may be performed as needed.

When the reaction in the fourth step is completed, the reaction is terminated. To terminate the reaction, for example water can be added.

After the reaction is completed, the third product prepared in the fourth step can be separated. In the step of separating the third product, for example, the organic layer may be phase separated, residual moisture may be dried, and the organic solvent may be removed. Drying of residual moisture can be performed using MgSO ₄ (Magnesium sulfate). Removal of the organic solvent can be done using a method known in the art, for example, using a vacuum rotary concentrator.

The third product prepared in the fourth step may be represented by the following formula (6).

[Formula 6]

In Formula 6, the definitions of substituents are the same as those in Formulas 1 to 3.

According to one example, Chemical Formula 6 may be expressed as Chemical Formula 6-1 below.

[Formula 6-1]

In Formula 6-1, the definitions of substituents are the same as those in Formulas 1 to 3.

According to another embodiment of the present specification, the fourth step further includes purifying the third product by recrystallization. The recrystallization may be performed by first dissolving the third product using a fifth solvent and then crystallizing the third product using a sixth solvent. EA (ethylene acetate) can be used as the fifth solvent, and 2-propanol can be used as the sixth solvent.

At this time, dimethyl sulfoxide (DMSO) or methyl tertiary butyl ether (MTBE) can be used instead of EA as the fifth solvent, and alcohols such as methanol, ethanol, 1-propanol, and butanol can be used instead of 2-propanol as the sixth solvent. You can.

According to another embodiment of the present specification, the production method further includes preparing the compound of Formula 1 before the first step.

According to one example, the step of preparing the compound of Formula 1 includes reacting a compound represented by the following Formula 11 and substituted or unsubstituted phenyl magnesium bromide (A); and

It includes a step (B) of reacting the product (a) obtained through step (A) and phenol. If necessary, step (B) may further include a process of purifying product (b) through a recrystallization process.

[Formula 11]

In Formula 11, X is a halogen group.

According to one example, reacting the compound represented by Formula 11 and substituted or unsubstituted phenyl magnesium bromide in a solvent (A); and a step (B) of reacting the product (a) obtained through step (A) with phenol in a solvent.

According to an exemplary embodiment of the present specification, X is F (fluorine), Cl (chlorine), Br (bromine), or I (iodine).

According to another exemplary embodiment, X is Br (bromine).

[Step (A)]

According to an exemplary embodiment of the present specification, step (A) is a step of reacting the compound represented by Formula 11 and substituted or unsubstituted phenyl magnesium bromide in a solvent.

According to one example, Chemical Formula 11 may be expressed as Chemical Formula 11-1 below.

[Formula 11-1]

In Formula 11-1, X is a halogen group.

The solvent used in step (A) may be tetrahydrofuran (THF), but is not limited thereto.

According to an exemplary embodiment of the present specification, step (A) may be performed at -30 °C to 10 °C, and preferably at -10 °C to 5 °C. When step (A) is performed in the above temperature range, there is an advantage that it has an appropriate reaction rate and no additional process equipment is required. Specifically, if the reaction temperature in step (A) proceeds above 10°C, there is a high possibility that the reaction will not proceed in the desired direction and impurities will be generated, and if the reaction temperature proceeds at a temperature lower than the above temperature range, the reaction may proceed in the desired direction. It progresses slowly and requires additional equipment to lower the reaction temperature. In particular, the process of synthesizing the organic compound of the present invention using butyllithium (n-BuLi), like the existing synthesis process, has the problem of requiring additional process equipment to lower the reaction temperature to extremely low temperature (about -78°C). there is.

In one embodiment of the present invention, in step (A), the molar ratio of the compound represented by Formula 11 and substituted or unsubstituted phenyl magnesium bromide (Formula 11: phenyl magnesium bromide) is about 1:1 to 1:2. It may be, preferably about 1:1.5 to 1:2. When the content of the compound represented by Formula 11 and the substituted or unsubstituted phenylmagnesium bromide satisfies the above range, the problem of lowering the overall yield that occurs when the content of the compound represented by Formula 11 is high can be prevented. , when the content of the substituted or unsubstituted phenyl magnesium bromide is high, there is an advantage in preventing economic loss due to unnecessary raw materials due to remaining phenyl magnesium bromide that does not participate in the reaction.

According to an exemplary embodiment of the present specification, step (A) may be carried out through the following process.

In the above reaction formula, R is hydrogen or an alkyl group.

In one embodiment of the present specification, step (A) may be performed for 10 hours to 72 hours, and more preferably for 15 hours to 24 hours. When the reaction time satisfies the above range, there is an advantage in that the highest yield can be obtained within the range in which no additional addition reaction occurs.

[Step (B)]

The method for producing an organic compound of the present invention includes the step (B) of reacting the product (a) obtained through step (A) and phenol.

According to another embodiment, a step (B) of reacting the product (a) obtained through step (A) and phenol in a solvent is included.

According to another exemplary embodiment, the product (a) is represented by the following formula (12).

[Formula 12]

In Formula 12, X is a halogen group, and R is hydrogen or an alkyl group.

For example, Chemical Formula 12 may be expressed as Chemical Formula 12-1 below.

[Formula 12-1]

In Formula 12-1, the definition of the substituent is the same as that in Formula 12.

The solvent used in step (B) may be dichloromethane, but is not limited thereto.

According to another embodiment, step (B) may further include additional compounds such as methane sulfonic acid, sulfuric acid, and p-toluenesulfonic acid, but is not limited thereto.

According to an exemplary embodiment of the present specification, in step (B), the molar ratio of the compound represented by Formula 12 and phenol (Formula 12: phenol) is about 1:3 to 1:6, 1:4 to 1:6. You can.

In one embodiment of the present specification, the molar ratio of the compound represented by Formula 12 and the additional compound (Formula 12: additional compound) in step (B) may be about 1:0.5 to 1:1.5.

In one embodiment of the present specification, in step (B), the molar ratio of the compound represented by Formula 12, phenol, and additional compounds such as methane sulfonic acid (Formula 2: phenol: additional compound) is about 1:5: It can be 1.

According to an exemplary embodiment of the present specification, step (B) may be carried out through the following process.

In the above reaction formula, R is hydrogen or an alkyl group.

According to another embodiment, step (B) may be performed at 15°C to 40°C, and preferably at 17°C to 25°C. If step (B) is outside the above temperature range, there is a problem that additional equipment is required or the boiling point of the solvent is exceeded and the reflux state is maintained.

In one embodiment of the present specification, step (B) may be performed for 5 hours to 24 hours, and more preferably for 15 hours to 18 hours. If the reaction time is outside the above range, there is a problem in that the yield decreases or additional reaction does not proceed.

According to an exemplary embodiment of the present specification, step (B) is a process of reacting the product (a) and phenol to obtain 'product (b) before purification'; and a process of purifying the product (b) through a recrystallization process of the 'product (b) before purification', and the recrystallization process may be performed at the end of step (B).

The process of purifying the product (b) is performed by adding a recrystallization solvent and stirring. According to an exemplary embodiment of the present specification, the step before adding the recrystallization solvent includes drying using a material such as magnesium sulfate (MgSO ₄ , magnesium sulfate) and removing the solvent.

According to an exemplary embodiment of the present specification, the recrystallization solvent used in the process of purifying the product (b) is n-butane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- It may be an aliphatic hydrocarbon-based solvent such as decane.

According to another embodiment, the recrystallization solvent used in the process of purifying the product (b) may be hexane, but is not limited thereto.

According to an exemplary embodiment of the present specification, the stirring time for the process of purifying the product (b) may be performed for 10 hours to 72 hours, and more preferably 15 hours to 24 hours. When the stirring time satisfies the above range, there is an advantage in that yield can be maximized.

The compound prepared by the above-described manufacturing method can be applied to a device using a solution process. For example, an organic layer of an organic light emitting device can be formed using a coating composition containing the above compound and a solvent.

In one embodiment of the present specification, the coating composition may be in a liquid form. The “liquid phase” means that it is in a liquid state at room temperature and pressure.

Solvents included in the coating composition include, for example, chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; Ether-based solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone-based solvents such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, Tetralone, Decalone, and Acetylacetone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyhydric acids such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. alcohol and its derivatives; Alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethyl sulfoxide; and amide-based solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; Solvents such as tetralin are exemplified, but any solvent capable of dissolving or dispersing the fluorene derivative according to an exemplary embodiment of the present invention is sufficient and is not limited thereto.

The solvent included in the coating composition may be used alone, or two or more solvents may be mixed.

In an exemplary embodiment of the present specification, the coating composition may further include one or two compounds selected from the group consisting of a compound having a thermosetting group or a photocurable group introduced into the molecule and a polymer compound.

In one embodiment of the present specification, the coating composition may further include a compound into which a thermosetting group or a photocurable group is introduced into the molecule. When the coating composition further includes a compound into which a thermosetting group or a photocurable group is introduced into the molecule, the degree of curing of the coating composition can be further increased.

In one embodiment of the present specification, the molecular weight of the compound in which a thermosetting group or a photocurable group is introduced into the molecule is 1,000 g/mol to 3,000 g/mol.

In one embodiment of the present specification, the coating composition may further include a polymer compound. When the coating composition further includes a polymer compound, the ink properties of the coating composition can be improved. That is, the coating composition further comprising the polymer compound can provide a viscosity suitable for coating or inkjet.

In one embodiment of the present specification, the coating composition may further include one or two or more additives selected from the group consisting of a thermal polymerization initiator and a photopolymerization initiator.

Examples of the thermal polymerization initiator include methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methylcyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, and 2,4-dichlorobenzoyl peroxide. oxide, bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, p-chlorol benzoyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-(t- Butyloxy)-hexane, 1,3-bis(t-butyl peroxy-isopropyl)benzene, t-butyl cumyl peroxide, di-tbutyl peroxide, 2,5-dimethyl-2,5- (di-t-butyl peroxy)hexane-3, tris-(t-butyl peroxy)triazine, 1,1-dit-butyl peroxy-3,3,5-trimethyl cyclohexane, 1,1-di t-butyl peroxy cyclohexane, 2,2-di(t-butyl peroxy) butane, 4,4-di-t-butyric acid cyclohexane, 2,2-bis(4) ,4-t-butyl peroxy cyclohexyl)propane, t-butyl peroxyisobutyrate, dit-butyl peroxy hexahydro terephthalate, t-butyl peroxy-3,5,5-trimethylhexaate, t -Peroxides such as butyl peroxybenzoate and dit-butyl peroxytrimethyl adipate, or azo systems such as azobis isobutylnitrile, azobisdimethyl valeronitrile, and azobis cyclohexyl nitrile, but are not limited to these. .

Examples of the photopolymerization initiator include diethoxy acetophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 4-(2-hydroxy ethoxy ) Phenyl-(2-hydroxy-2-propyl) ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl) butanone-1,2-hydroxy-2-methyl-1- Phenyl propan-1-one, 2-methyl-2-morpholino (4-methyl thio phenyl) propan-1-one, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl) Acetophenone-based or ketal-based photopolymerization initiators such as oxime, benzoin such as benzoin, benzoin methyl atel, benzoin ethyl atel, benzoin isobzyle atel, benzoin isopropyl atel, etc. Ether-based photopolymerization initiators, benzophenone, 4-hydroxybenzophenone, 2-benzoyl naphthalene, 4-benzoyl biphenyl, 4-benzoyl phenyl ether, acrylated benzophenone, 1,4-benzoyl benzene, etc. Thioxanthone-based photopolymerization of 2-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, etc. Initiators and other photopolymerization initiators include ethyl anthraquinone, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,4,6-trimethylbenzoyl phenyl ethoxy phosphine oxide, and bis(2,4,6-trimethylbene). Zoyl) phenyl phosphine oxide, bis(2,4-dimethoxy benzoyl)-2,4,4-trimethyl pentylphosphine oxide, methylphenyl glycoxyester, 9,10-phenanthrene, acridine-based compound , triazine-based compounds, and imidazole-based compounds. Additionally, those having a photopolymerization acceleration effect can be used alone or in combination with the photopolymerization initiator. For example, triethanolamine, methyl diethanol amine, 4-dimethylamino ethyl benzoate, 4-dimethylamino isoamyl benzoate, ethyl benzoate (2-dimethylamino), 4,4'-dimethylaminobenzophenone, etc. This is not limited.

In one embodiment of the present specification, the coating composition does not further include a p-doping material.

In one embodiment of the present specification, the coating composition further includes a p-doping material.

In this specification, the p-doping material refers to a material that causes the host material to have p-semiconductor characteristics. The p semiconductor characteristic refers to the characteristic of injecting or transporting holes at the HOMO (highest occupied molecular orbital) energy level, that is, the characteristic of a material with high hole conductivity.

In an exemplary embodiment of the present specification, the p-doping material may be F4TCNQ or a farylborate-based compound as shown in the following formulas 7-1 to 7-3, but is not limited thereto.

[Formula 7-1]

[Formula 7-2]

[Formula 7-3]

In this specification, the p-doping material is sufficient as long as it has p-semiconductor properties, and one type or two or more types can be used, and the type is not limited.

In one embodiment of the present specification, the content of the p-doping material is 0% by weight to 50% by weight based on 100% by weight of the fluorene-based compound of Formula 6.

In one embodiment of the present specification, the content of the p-doping material includes 0 to 30% by weight based on the total solid content of the coating composition.

In one embodiment of the present specification, the content of the p-doping material is preferably 1 to 30% by weight based on the total solid content of the coating composition, and in another embodiment, the p-doping material It is more preferable that the content includes 10 to 30% by weight based on the total solid content of the coating composition.

In another embodiment, the coating composition is a single molecule containing a thermosetting group or a photocuring group; Alternatively, it may further include a single molecule containing a terminal group capable of forming a polymer by heat. A single molecule containing a thermosetting group or a photocuring group as described above; Alternatively, the compound may have a single molecule containing a terminal group capable of forming a polymer by heat and have a molecular weight of 2,000 g/mol or less.

In one embodiment of the present specification, the coating composition has a molecular weight of 2,000 g/mol or less and is a single molecule containing a thermosetting group or a photocuring group; Or, it further includes a single molecule containing a terminal group capable of forming a polymer by heat.

A single molecule containing the thermosetting or photocuring group; Alternatively, single molecules containing terminal groups capable of forming polymers by heat include aryl of phenyl, biphenyl, fluorene, and naphthalene; Arylamine; Alternatively, it may refer to a single molecule in which fluorene is substituted with a thermosetting group, a photocurable group, or a terminal group capable of forming a polymer by heat.

In another embodiment, the viscosity of the coating composition is 2 cP to 15 cP.

This specification also provides an organic light-emitting device formed using the coating composition.

In one embodiment of the present specification, a first electrode; second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers are formed using the coating composition or a cured product thereof. The cured product of the coating composition refers to a state in which the coating composition has been cured by heat treatment or light treatment.

In one embodiment of the present specification, the organic material layer containing the coating composition or a cured product thereof is a hole transport layer, a hole injection layer, or a layer that performs hole transport and hole injection simultaneously.

In another embodiment, the organic layer containing the coating composition or a cured product thereof is a light-emitting layer.

In one embodiment of the present specification, the organic light emitting device is a hole injection layer or a hole transport layer. It further includes one or two layers selected from the group consisting of an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes an organic material layer, a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, a light emitting layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and electron transport layer. It may have a structure that includes layers that simultaneously do the following. However, the structure of the organic light emitting device is not limited to this and may include fewer organic layers.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

The organic light emitting device of the present specification is known in the art, except that at least one layer of the organic material layer is formed using a coating composition containing a compound for solution processing prepared using the compound represented by Formula 5 as an intermediate. It can be manufactured using materials and methods.

For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, an anode is formed by depositing a metal, a conductive metal oxide, or an alloy thereof on the substrate using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and a layer that simultaneously performs electron injection and electron transport through a deposition or solution process, and then depositing a material that can be used as a cathode on it. You can. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

This specification also provides a method of manufacturing an organic light-emitting device formed using the coating composition.

Specifically, in one embodiment of the present specification, preparing a substrate; forming a first electrode on the substrate; Forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein at least one layer of the organic layer is formed using the coating composition.

According to an exemplary embodiment of the present specification, the organic material layer formed using the coating composition is formed using a solution process.

In one embodiment of the present specification, the organic material layer formed using the coating composition is formed using spin coating.

In another embodiment, the organic layer formed using the coating composition is formed by a printing method.

In the context of the present specification, the printing method includes, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited thereto.

The coating composition according to an exemplary embodiment of the present specification is suitable for a solution process due to its structural characteristics and can be formed by a printing method, so it is economical in terms of time and cost when manufacturing a device.

In one embodiment of the present specification, forming an organic material layer formed using the coating composition includes coating the coating composition on the cathode or anode; and heat-treating or light-treating the coated coating composition.

In one embodiment of the present specification, the heat treatment temperature in the heat treatment step is 85 ℃ to 250 ℃.

In another embodiment, the heat treatment time in the heat treatment step may be 1 minute to 1 hour.

The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : Combination of metal and oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

The hole injection layer is a layer that injects holes from the electrode. The hole injection material has the ability to transport holes and has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and the hole injection material generated in the light-emitting layer A compound that prevents movement of excitons to the electron injection layer or electron injection material and has excellent thin film forming ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. These include organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited to these.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and has high mobility for holes. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

The light-emitting material is a material that can emit light in the visible light range by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.

The light emitting layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periplanthene, and styrylamine compounds include substituted or unsubstituted arylamino groups. It is a compound in which at least one arylvinyl group is substituted on the arylamine, and is substituted or unsubstituted with one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light-emitting layer. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer. A material with high electron mobility is suitable. do. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light-emitting layer or a light-emitting material, and hole injection of excitons generated in the light-emitting layer. A compound that prevents movement to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.

Examples of the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.

The hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.

The organic light emitting device according to the present specification may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.

Hereinafter, in order to explain the present specification in detail, examples will be given in detail. However, the embodiments according to the present specification may be modified into various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described below. The embodiments of this specification are provided to more completely explain the present specification to those with average knowledge in the art.

<Experimental example>

Example 1

One)

[Compound A]

2)

[Compound A] [Compound B]

3)

[Compound B] [Compound 1]

1) 120 g (255.6 mmol, 2.05 eq) of 4-(2-bromo-9-(4-(tert-butyl)phenyl)-9H-fluoren-9-yl)phenol, N,N'- 41.9 g (124.7 mmol, 1.0 eq) of diphenylbenzidine, 59.9 g (623.5 mmol, 5.0 eq) of sodium tert-butoxide, and 3.2 g (6.23 mmol, 0.05 eq) of Pd(t-Bu ₃ P) ₂ were dissolved in 1 L of toluene. After dissolving in , the temperature was raised to 85°C under a nitrogen atmosphere and reacted for 1 hour. Afterwards, the temperature was lowered to room temperature and 1 L of H ₂ O was added to terminate the reaction. The organic layer was phase-separated, the residual moisture was dried using MgSO ₄ , and the organic solvent was removed using a vacuum rotary concentrator. 720 ml of DMSO was added to the concentrated crude Compound A to dissolve it, and then 2160 ml of water and ethanol were mixed at a volume ratio of 1:3.5 to obtain 210.6 g of ivory solid Compound A (yield 74%).

2) After adding 2 L of DMSO to 210.6 g of Compound A, K ₂ CO ₃ (104.6 g, 756.7 mmol), and 4-fluorobenzaldehyde (81.2 ml, 756.7 mmol), the oil temperature was set to 80°C and 5 It was maintained for some time. Afterwards, the reaction was terminated by adding 5 L of H ₂ O, and then cooled to room temperature. The resulting solid was filtered, washed with water, and dried in a vacuum oven at 80°C.

The dried solid was dissolved in 210 ml of DMSO and then 840 ml of 2-propanol was added to obtain 197.5 g of Compound B (yield 79%).

3) 106.8 g (298.89 mmol, 2.0 eq) of methyltriphenylphosphonium bromide, 33.5 g (298.89 mmol, 2.0 eq) of potassium tert-butoxide, and 600 ml of anhydrous THF were added to a glassware and an inert atmosphere was created at 0°C. Compound B 197.5 g (149.4 mmol, 1.0 eq) was dissolved in 400 ml of anhydrous THF and then added dropwise to the vitrine. After stirring for 1 hour, 600 ml of H ₂ O was added to terminate the reaction, the organic layer was separated, the residual moisture was dried using MgSO ₄ , and the organic solvent was removed using a vacuum rotary concentrator. 200 ml of EA (ethyl acetate) was added and dissolved in the concentrated crude compound 1, and then 800 ml of IPA was added to obtain 167 g of solid compound 1 (yield 85%).

A mass measurement graph of the manufactured final product is shown in Figure 1. The vertical axis in Figure 1 represents intensity, and the horizontal axis represents m/z values. LC mass analysis was performed using an LTQ mass spectrometer (Thermo, USA) using a Capcellpak C18 (4.6mm id x 50 mmL, 3㎛) column, and solvent A was acetonitrile and tetrahydrofuran (THF) in volume ratio Compound 1 with a molecular weight of 1316 g/mol was detected at 278 nm using a composition of 50% and 50%, and solvent B containing 100% and 1% of H ₂ O and acetonitrile by volume.

Comparative Example 1

[Compound T-1] [Compound T-2]

[Compound T-3]

First, 120 g (255.6 mmol, 1.0 eq) of 4-(2-bromo-9-(4-(tert-butyl)phenyl)-9H-fluoren-9-yl)phenol and 42.5 g of 4-nitrobenzaldehyde. (281.2 mmol, 1.1 eq), 91.6 g (281.2 mmol, 1.1 eq) of cesium carbonate, and 2.4 g (12.78 mml, 0.05 eq) of copper acetate (II) were dissolved in 850 ml of DMF, then the oil temperature was set to 100°C and 12 It was stirred for over an hour and overnight. The reaction was terminated by adding saturated NH ₄ Cl(aq), the organic layer was separated, the residual moisture was dried using MgSO ₄ , and the organic solvent was removed using a vacuum rotary concentrator. 700 ml of ethanol was added to the concentrated crude Compound T-1 and stirred overnight to obtain 115.8 g (79% yield) of Compound T-1 as an ivory solid.

144.3 g (403.82 mmol, 2.0 eq) of methyltriphenylphosphonium bromide, 45.3 g (403.82 mmol, 2.0 eq) of potassium tert-butoxide, and 600 ml of anhydrous THF were added to a glassware, and an inert atmosphere was created at 0°C. 115.8 g (201.91 mmol, 1.0 eq) of Compound T-1 was dissolved in 400 ml of anhydrous THF and then added dropwise to a glass jar. After stirring for one hour, 600 ml of H ₂ O was added to terminate the reaction, and then crude compound T-2 in solid state was obtained by column purification and vacuum rotary concentrator. 1 L of ethanol was added to the concentrated crude compound T-2 and stirred overnight to obtain 99.3 g of solid compound T-2 (yield 86%).

Compound T-2 99.3 g (174 mmol, 2.05 eq), N,N'-diphenylbenzidine 28.5 g (84.75 mmol, 1.0 eq), sodium tert-butoxide 32.6 g (33.90 mmol, 4.0 eq), Pd(t 2.6 g (5.08 mmol, 0.06 eq) of -Bu3P)2 was dissolved in 800 ml of toluene, then heated to 85°C under a nitrogen atmosphere and reacted for 1 hour. Afterwards, the temperature was lowered to room temperature and 600 ml of H ₂ O was added to complete the reaction. Crude compound T-3 in solid state was obtained using column purification and vacuum rotary concentrator. 3 L ethanol was added to the concentrated crude compound T-3 and stirred overnight to obtain 150 g of solid compound T-3 (yield 66%).

The yields of each step in the manufacturing process of Example 1 and Comparative Example 1 are listed in Table 1 below.

Example 1 Comparative Example 1 Yield of first step 74% 79% Yield of third step 79% 86% Yield of Step 4 85% 66% final yield 50% (167 g) 45% (150 g)

Compared to Comparative Example 1, in Example 1, not only is there no need to use a solvent requiring special management, but the intermediate and final products can be purified by recrystallization, so the amount of solvent used is greatly reduced and the process time is greatly shortened. . Additionally, compared to Comparative Example 1, the final yield was greatly increased in Example 1.

Claims (11)

A first step of reacting a compound of Formula 1 below with a compound of Formula 2 below to obtain a first product; and
A method for producing an organic compound represented by any one of the following formula 5 and the following formula 6, comprising a second step of introducing a thermosetting group or a photocurable group in place of H of the OH group of the first product:
[Formula 1]

[Formula 2]

[Formula 5]

[Formula 6]

In Formulas 1 and 2,
Ar1 to Ar3 and Ar1' are the same or different from each other and are substituted or unsubstituted aryl groups,
L is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
X1 is a halogen group,
The thermosetting group or photocuring group has one of the structures below,

is a portion connected instead of H of the OH group of the first product,
The term 'substituted or unsubstituted' refers to hydrogen; heavy hydrogen; halogen group; Nitrile group; nitro group; hydroxyl group; Alkyl group; Alkoxy group; alkenyl group; Aryl group; and substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group, or substituted or unsubstituted with two or more substituents among the above-exemplified substituents linked. The method of claim 1, wherein the second step is
A third step of obtaining a second product by reacting the first product with a compound having a thermosetting group or a photocurable group containing a ketone group; and
The ketone group of the second product is converted to an alkene group. A method for producing an organic compound comprising a fourth step of obtaining a third product having a thermosetting group or a photocuring group. The method of claim 1, wherein the first step further includes purifying the first product by recrystallization. The method of claim 1, wherein the second step further includes purifying the organic compound by recrystallization. The method of claim 2, wherein the third step further includes purifying the second product by recrystallization. The method of claim 2, wherein the fourth step further includes purifying the third product by recrystallization. The method for producing an organic compound according to claim 2, wherein the compound having a thermosetting group or a photocurable group containing a ketone group in the third step is represented by the following formula (4):
[Formula 4]

X2 is a halogen group or nitro group. The method for producing an organic compound according to claim 2, wherein the third product is represented by the following formula (6):
[Formula 6]

In Formula 6, the definitions of Ar1, Ar2, Ar3, and L are the same as those in Formulas 1 and 2, and Ar1' is the same as or different from Ar1 to Ar3 and is an aryl group substituted or unsubstituted by an alkyl group. The method of claim 1, further comprising preparing the compound of Formula 1 before the first step. The method of claim 9, wherein the step of preparing the compound of Formula 1 includes
Step (A) of reacting a compound represented by the following formula (11) and phenyl magnesium bromide substituted or unsubstituted with an alkyl group; and
A method for producing an organic compound comprising the step (B) of reacting the product (a) obtained through step (A) and phenol:
[Formula 11]

In Formula 11, X is a halogen group. The method of claim 10, wherein step (B) further includes purifying product (b) through a recrystallization process.