JP2000212130A - New monoalkoxycarbonylmethylated trisphenols and their production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound having excellent compatibility with a solvent of photoresist and a base polymer, useful as an acid decomposable dissolution inhibitor. SOLUTION: This compound is shown by formula I (R1 is a 1-6C alkyl or a 5-6C cycloalkyl; R2 is a 1-4C alkyl or a 1-4C alkoxyalkyl; R3 is R1; m is 0-2; n is 0-3) such as a compound of formula II. The compound of formula I is obtained by reacting an alkoxycarbonylmethoxybenzaldehyde of formula III with a phenol of formula IV in the presence of an acid catalyst (e.g. hydrochloric acid, sulfuric acid or p-toluenesulfonic acid). The compound of formula III is a new compound and is obtained, for example, by reacting a hydroxybenzaldehyde of formula V with t-butyl chloroacetate, etc., in dimethylformamide in the presence of potassium carbonate.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel monoalkoxycarbonylmethylated trisphenol and a method for producing the same, and more particularly, to a monosulfonated trisphenol which can be suitably used as a dissolution inhibitor for a chemically amplified resist. Alkoxycarbonyl methyl ethers, especially
The present invention relates to t-butoxycarbonyl methyl ethers and a method for producing the same. Furthermore, the present invention relates to alkoxycarbonylmethoxybenzaldehydes, which are novel compounds as raw materials for producing the above-mentioned monoalkoxycarbonylmethyl ethers of trisphenols.

[0002]

2. Description of the Related Art Conventionally, using a positive photoresist,
Although microfabrication of semiconductors is widely performed,
Against this background, the degree of integration of integrated circuits has been further increased in recent years. In the production of semiconductor substrates such as VLSIs, processing of ultrafine patterns having a line width of 0.5 μm or less is required. It has been needed. In order to achieve such a resolution, the wavelength used in an exposure apparatus used for photolithography is becoming shorter and shorter. Recently, far ultraviolet light and excimer laser light (XeC laser light) have been used.
1, KrF, ArF, etc.) are being studied for practical use.

However, when a conventional positive photoresist made of a novolak resin and a naphthoquinonediazide compound is patterned using radiation such as far ultraviolet light or excimer laser light, the novolak resin and the naphthoquinonediazide compound are exposed in the radiation region. Due to the strong absorption, it is difficult for the radiation to reach the bottom of the photoresist layer, and an accurate pattern is not formed.

In order to solve such a problem, a chemically amplified resist composition has been proposed. Conventionally, a two-component positive photoresist and a three-component positive photoresist are known as the chemically amplified resist composition. Among them, for example, the three-component positive photoresist is a radiation-sensitive material. A so-called acid-decomposable dissolution inhibitor is compounded in a photoresist comprising a compound (acid generator) that absorbs acid and generates an acid and an alkali-soluble polymer (base polymer) such as poly (p-hydroxystyrene). Irradiation of radiation such as far ultraviolet light or excimer laser light to generate an acid in the acid generator in the exposed portion, and using this acid as a catalyst to cause a chemical reaction in the dissolution inhibitor, thus producing radiation. Is to increase the solubility of the photoresist in an alkali developing solution only in the exposed portions irradiated with, to form a positive image with high contrast.

The above-mentioned acid-decomposable dissolution inhibitor has, as basic requirements, excellent transparency (ie, transparency) of radiation such as far-ultraviolet light and excimer laser light.
It is desirable that the photoresist has excellent compatibility with the solvent and the base polymer, and that the etching resistance of the image area be improved at the time of development. However, no dissolution inhibitor satisfying all of these has been hitherto known.

[0006]

DISCLOSURE OF THE INVENTION The present inventors have made intensive studies to solve the above-mentioned problems in the chemically amplified resist composition, and as a result, have found that trisphenol monoalkoxycarbonyl methyl ethers, in particular, The inventors have found that trisphenylmethane-type mono-t-butoxycarbonylmethyl ethers of trisphenol can meet the above-mentioned requirements, and have accomplished the present invention. That is, an object of the present invention is to provide monoalkoxycarbonyl methyl ethers of trisphenols which are useful as an acid-decomposable dissolution inhibitor in a chemically amplified resist composition.

Conventionally, the etherification of the hydroxyl group of trisphenols is generally carried out by a condensation reaction between a halogenated acetic acid ester and trisphenols. According to this reaction, a particular one of the three hydroxyl groups is selected. It is not possible to selectively etherify only hydroxyl groups. For example, even if 1/3 part by mole of the etherifying agent is used per 1 part by mole of trisphenols, it is not possible to selectively etherify only the selected hydroxyl group among the three hydroxyl groups.

Therefore, according to the present invention, the hydroxyl groups of hydroxybenzaldehydes are previously converted into alkoxycarbonylmethyl ethers, which are then condensed with phenols to etherify only the hydroxyl groups of trisphenols that are particularly selected. The present inventors have found that monoalkoxycarbonyl methyl ethers of trisphenols can be easily obtained, and have reached the present invention. That is, an object of the present invention is to provide a method for producing the above-mentioned monoalkoxycarbonyl methyl ethers of trisphenols.

Another object of the present invention is to provide alkoxycarbonylmethoxybenzaldehydes, which are novel compounds useful as raw materials for producing the above-mentioned monoalkoxycarbonylmethyl ethers of trisphenols.

[0010]

The basic properties of such an acid-decomposable dissolution inhibitor are required to be excellent in compatibility with a photoresist solvent and a base polymer. As a result of intensive research, monoalkoxycarbonyl methyl ethers of trisphenols,
In particular, the inventors have found that t-butoxycarbonyl methyl ethers can be easily obtained, and furthermore, have found that this novel compound satisfies the above-mentioned requirements, and have reached the present invention.

That is, the present invention relates to monoalkoxycarbonyl methyl ethers of trisphenols, particularly t-butoxycarbonyl methyl ethers, which are useful as an acid-decomposable dissolution inhibitor in a chemically amplified resist composition, and a method for producing the same. The purpose is to provide.

[0012]

SUMMARY OF THE INVENTION The novel monoalkoxycarbonylmethylated trisphenols according to the present invention are:
General formula (I)

[0013]

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(Wherein R ₁ represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms;
₂ represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms; R ₃ represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms; An integer of 2; n is an integer of 0 to 3;
In the above, R ₂ may be the same or different, and when n is 2 or more, R ₃ may be the same or different. ).

According to the invention, such monoalkoxycarbonylmethylated trisphenols according to the invention have the general formula (II)

[0016]

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(Wherein R ₁ represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms;
₂ represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms, m is an integer of 0 to 2, and when m is 2 or more, R ₂ may be mutually the same, May be. Novel alkoxycarbonylmethoxybenzaldehydes represented by the general formula (III) in the presence of an acid catalyst:

[0018]

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(Wherein R ₃ represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms;
Is an integer of 0 to 3, and when n is 2 or more, R ₃ may be mutually the same or different. )) Can be obtained by reacting the phenol.

[0020]

DETAILED DESCRIPTION OF THE INVENTION The novel monoalkoxycarbonylmethylated trisphenols according to the present invention have the general formula (I)

[0021]

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(Wherein R ₁ represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms;
₂ represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms; R ₃ represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms; An integer of 2; n is an integer of 0 to 3;
In the above, R ₂ may be the same or different, and when n is 2 or more, R ₃ may be the same or different. ).

In the monoalkoxycarbonylmethylated trisphenol represented by the general formula (I),
R ₁ is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms. Therefore, R ₁ is specifically a methyl group, an ethyl group, a propyl group, a butyl group,
When it is an alkyl group such as a pentyl group or a hexyl group, or a cycloalkyl group such as a cyclopentyl group or a cyclohexyl group, and is an alkyl group having 3 or more carbon atoms, it is straight-chain or branched. May be. Similarly, R ₂ is an alkyl group having 1 to 4 carbon atoms or 1 carbon atom.
To 4 alkoxyl groups. Accordingly, R ₂ is specifically an alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, or a methoxyl group, an ethoxyl group, a propoxyl group or a butoxyl group, When it is 3 or more alkyl groups, it may be linear or branched, and when it is an alkoxyl group having 3 or more carbon atoms, the alkyl group contained therein is linear, branched or Either may be used. Further, when m is 2 or more, R ₂ may be the same or different, and when n is 2 or more, R ₃ may be the same or different. However, particularly preferably, m is 0 and R ₁ is a t-butyl group.

Accordingly, examples of preferred monoalkoxycarbonylmethylated trisphenols according to the present invention include, for example, 4,4'-bis (1-hydroxy-2-cyclohexyl-5-methylphenyl) methyl-2-t-butoxy Carbonylmethoxybenzene can be mentioned. According to the present invention, such a monoalkoxycarbonylmethylated trisphenol is represented by the general formula (II):

[0025]

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(Wherein R ₁ represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms;
₂ represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms, m is an integer of 0 to 2, and when m is 2 or more, R ₂ may be mutually the same, May be. In the presence of an acid catalyst, an alkoxycarbonylmethoxybenzaldehyde represented by the formula (III)

[0027]

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(Wherein R ₃ represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms;
Is an integer of 0 to 3, and when n is 2 or more, R ₃ may be mutually the same or different. )) Can be obtained by reacting the phenol.

In the alkoxycarbonylmethoxybenzaldehydes represented by the general formula (II), as described above, R ₁ is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms. Therefore,
R ₁ is specifically an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a hexyl group, or a cycloalkyl group such as a cyclopentyl group or a cyclohexyl group. When it is an alkyl group having 3 or more carbon atoms, it may be linear or branched. Similarly, R ₂ is an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms.
₂ is, specifically, an alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, or a methoxyl group, an ethoxyl group, a propoxyl group or a butoxyl group, having 3 or more carbon atoms. When it is an alkyl group, it may be linear or branched, and when it is an alkoxyl group having 3 or more carbon atoms, the alkyl group contained therein may be linear or branched. . When m is 2 or more, R ₂ may be the same or different, and when n is 2 or more, R ₃ may be the same or different. However, particularly preferably, m is 0 and R ₁ is a t-butyl group.

Thus, as an example of the preferred alkoxycarbonylmethoxybenzaldehydes according to the present invention,
For example, 2-t-butoxycarbonylmethoxybenzaldehyde, 4-t-butoxycarbonylmethoxybenzaldehyde, 3-t-butoxycarbonylmethoxybenzaldehyde and the like can be mentioned.

First, the reaction between an alkoxycarbonylmethoxybenzaldehyde and a phenol represented by the general formula (III) will be described. This reaction is usually
In an alcohol solvent in the presence of an acid catalyst, based on 1 mol part of alkoxycarbonylmethoxybenzaldehydes,
The phenols are reacted in an amount of 2 mol parts or more, usually 2 to 10 mol parts, preferably 3 to 6 mol parts.

The alcohol solvent may be selected from the group consisting of methanol, ethanol, isopropyl alcohol, n-propyl alcohol, t-butyl alcohol, and the like, in consideration of the reaction raw materials used, the solubility of the obtained product, reaction conditions, and the economics of the reaction. Lower aliphatic alcohols such as isobutyl alcohol and n-butyl alcohol are preferably used. Particularly, methanol is preferably used.

Such alcohol solvents are usually used alkoxycarbonylmethoxybenzaldehydes 1
The amount is used in the range of 10 to 1000 parts by weight, preferably 40 to 400 parts by weight with respect to 00 parts by weight, but is not limited thereto.

The acid catalyst is preferably an acid soluble in an alcohol solvent which is a reaction solvent.
Preferred specific examples include hydrochloric acid, sulfuric acid, sulfuric anhydride, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, oxalic acid, formic acid, phosphoric acid, trichloroacetic acid, trifluoroacetic acid, and the like. Such an acid catalyst is, for example, in the case of 35% hydrochloric acid, 1 to 500 parts by weight, preferably 20 to 10 parts by weight, per 100 parts by weight of alkoxycarbonylmethoxybenzaldehydes.
It is used in the range of 0 parts by weight.

The reaction is usually carried out at 0 ° C. to 80 ° C., preferably at 0 ° C. to 50 ° C., while stirring under a nitrogen stream.
It may be carried out for about 72 hours, usually about 1 to 24 hours.

After the completion of the reaction, an alkali such as aqueous ammonia or an aqueous sodium hydroxide solution is added to the obtained reaction mixture to neutralize the acid catalyst, the aqueous layer is separated, and the solvent is distilled off from the obtained oil layer under reduced pressure. After distilling off, an aromatic hydrocarbon, an aliphatic hydrocarbon, an aliphatic ketone or a mixed solvent of two or more of these are added as a crystallization solvent to the obtained distillation residue, dissolved, and then cooled, The desired monoalkoxycarbonylmethylated trisphenol is crystallized, and thus a highly purified product thereof can be easily obtained.

The above-mentioned crystallization solvent is, for example, an aromatic hydrocarbon in consideration of crystallization conditions, purification effect, economy and the like.
Toluene, xylene, cumene and the like can be mentioned. As the aliphatic hydrocarbon, for example, n-pentane, n-hexane, isohexane, n-heptane, n-octane,
Examples thereof include isooctane, n-decane, 2,2-dimethylbutane, petroleum ether, petroleum benzene, ligroin, kerosene, petroleum spirit, petroleum naphtha, 2-pentene, mixed pentene, cyclohexane, methylcyclohexane, and the like. As the aliphatic ketone, for example,
Examples thereof include isopropyl ketone, methyl ethyl ketone, methyl isobutyl ketone, and diisopropyl ketone.

[0038] Such a crystallization solvent is usually added in an amount of 20 to 1000 parts by weight, preferably 50 to 500 parts by weight, based on 100 parts by weight of the reaction mixture, so that the desired solution can be obtained from the reaction solution. Monoalkoxycarbonylmethylated trisphenols can be crystallized with high purity. By recrystallizing the monoalkoxycarbonylmethylated trisphenols thus obtained by using the above-mentioned crystallization solvent as needed, a higher purity product can be obtained.

The above-mentioned alkoxycarbonylmethoxybenzaldehydes, which are raw materials used for producing the monoalkoxycarbonylmethylated trisphenols according to the present invention, are also novel compounds. The alkoxycarbonylmethoxybenzaldehydes are represented by the corresponding hydroxybenzaldehydes, ie, those represented by the general formula (IV)

[0040]

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(Wherein, R ₂ represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms, and m represents 0 to 2)
And when m is 2 or more, R ₂ may be the same or different. A) a suitable reaction solvent for the hydroxybenzaldehyde represented by, for example,
For example, it can be obtained by reacting t-butyl halide such as t-butyl chloroacetate or t-butyl bromoacetate in dimethylformamide in the presence of potassium carbonate. The t-butyl halide is generally used in an amount of 1 to 5 parts by mol based on 1 part by mol of the hydroxybenzaldehyde, and the potassium carbonate is usually used in an amount of 1 part by mol based on 1 part by mol of the hydroxybenzaldehyde. It is used in the range of 3 to 3 mole parts. The reaction is usually performed at a temperature in the range of 30 to 120 ° C. for several hours, for example,
It may be performed for 2 to 20 hours.

After completion of the reaction, an appropriate organic solvent, for example, toluene, cyclohexane or the like, and water are added to the reaction mixture, and the mixture is washed and separated. If necessary, the organic layer is washed and neutralized with an aqueous acid solution. By distilling off the solvent from the organic layer, adding an aliphatic lower alcohol such as methanol or an aliphatic hydrocarbon such as n-heptane to the residue, and crystallizing or distilling the residue. Can be obtained.

[0043]

In general, it is easy to alkoxycarbonylmethylate all of the hydroxyl groups of trisphenols, but it is very difficult to alkoxycarbonylmethylate only a part of the hydroxyl groups of trisphenols. Furthermore, it is impossible to obtain a reaction product in which only one hydroxyl group selected from among the hydroxyl groups of trisphenols is alkoxycarbonylmethylated with high purity and high yield.

According to the present invention, the hydroxyl group of hydroxybenzaldehydes is protected with an alkoxycarbonylmethyl group, and then this is condensed with a phenol to obtain the desired novel monoalkoxycarbonyl of trisphenol. Methyl ethers, especially t-
Butoxycarbonyl methyl ethers can be easily obtained.

Moreover, the monoalkoxycarbonyl methyl ethers of trisphenols, especially t-butoxycarbonyl methyl ethers, according to the present invention have two alkoxy groups and the above alkoxycarbonylmethoxy group in the molecule. Since it has excellent compatibility with the photoresist solvent and the base polymer, it is useful as an acid-decomposable dissolution inhibitor as described above.Moreover, for example, all the hydroxyl groups of trisphenols are alkoxycarbonylmethyletherified. It is useful for adjusting the solubility by using the acid-decomposable dissolution inhibitor in combination at an appropriate ratio.

[0046]

EXAMPLES The present invention will be described below with reference to examples.
The present invention is not limited by these examples.

Example 1 (Production of 2-t-butoxycarbonylmethoxybenzaldehyde) 366 g of dimethylformamide and 165.9 g (1.2 mol) of potassium carbonate were charged into a flask, and 122 g (1 mol) of salicylaldehyde was added dropwise thereto. did.
At a temperature of 50 ° C., 181.2 g of t-butyl chloroacetate was added.
(1.2 mol) was added dropwise over 3 hours. After dropping, 50 ° C
For 3 hours. Toluene 12 was added to the obtained reaction mixture.
2 g and 662 g of water were added and washed with water. 130 g of the solvent was distilled off, and 122 g of n-heptane was added to the residue for crystallization. After filtration, 122.3 g (purity: 98.5%) of 2-t-butoxycarbonylmethoxybenzaldehyde was removed from brown to pale yellow. Obtained as crystals. Further, the filtrate was concentrated to give 2-
t-butoxycarbonylmethoxybenzaldehyde 52.
6 g (purity 98.0%) were obtained. The overall yield was 74%. Melting point: 68.6 ° C. (DSC method) Infrared absorption spectrum: shown in FIG. Proton nuclear magnetic resonance spectrum (60 MHz, CDCl
₃ solvents, δ (ppm)):

[0048]

[Table 1]

Example 2 (Production of 4-t-butoxycarbonylmethoxybenzaldehyde) 366 g of dimethylformamide and 165.9 g (1.2 mol) of potassium carbonate were charged into a flask, and 122 g (1 mol) of 4-hydroxybenzaldehyde was added thereto.
Was added dropwise. At a temperature of 50 ° C., 181.2 g (1.2 mol) of t-butyl chloroacetate was added dropwise over 2 hours. After completion of the dropwise addition, the mixture was stirred at 50 ° C for 2 hours, and further stirred at 70 ° C for 3 hours. 122 g of toluene and 6 parts of water were added to the obtained reaction mixture.
62 g was added and washed with water. Under reduced pressure, 100 g of the solvent was distilled off, and 236 g of n-heptane was added to the residue for crystallization. After filtration, 128.4 g (purity: 99.9%) of 4-t-butoxycarbonylmethoxybenzaldehyde was obtained in white. Obtained as crystals. The yield was 54%. Melting point: 58.4 ° C. (DSC method) Infrared absorption spectrum: shown in FIG. Proton nuclear magnetic resonance spectrum (60 MHz, CDCl
₃ solvents, δ (ppm)):

[0050]

[Table 2]

Example 3 (4,4'-bis (1-hydroxy-2-cyclohexyl-
Preparation of 5-methylphenyl) methyl-2-t-butoxycarbonylmethoxybenzene
38 g (0.2 mol) of 6-cyclohexylphenol, 20 g of methanol and 4.8 g of 35% hydrochloric acid were charged at a temperature of 0 ° C. The mixture obtained in Example 1 was added to this mixture.
-T-butoxycarbonylmethoxybenzaldehyde 2
3.6 g (0.1 mol) were added dropwise at a temperature of 0 ° C intermittently in one hour. Then, after stirring at 0 ° C. for 7 hours and at room temperature for 13 hours, 48 g of toluene was added to the obtained reaction mixture,
Washing was performed by adding 50 g of an 8% aqueous sodium hydroxide solution.
After washing with water, it was washed with 50 g of a 1% aqueous oxalic acid solution, and further washed with water, and then the solvent was distilled off under reduced pressure at an internal temperature of 90 ° C. or lower. Next, 50 g of toluene was added to the residue to dissolve it. Then, 100 g of n-heptane was added, and the mixture was crystallized and filtered to obtain the desired 4,4′-bis (1-hydroxy-2-cyclohexyl-5-butylene). Methylphenyl) methyl-2-t-butoxycarbonylmethoxybenzene 92.
43.0 g of white crystals containing 5% were obtained. The yield was 72%. The crystals were recrystallized from cyclohexane. Melting point: 178.7 ° C. (Mettler method) Infrared absorption spectrum (cm ⁻¹ ): 3446 (νO
H), 1732 (νCOO) proton nuclear magnetic resonance spectrum (60 MHz, DMSO
-D6 solvent):

[0052]

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[0053]

[Table 3]

[Brief description of the drawings]

FIG. 1 is an infrared absorption spectrum of 2-t-butoxycarbonylmethoxybenzaldehyde.

FIG. 2 is an infrared absorption spectrum of 4-t-butoxycarbonylmethoxybenzaldehyde.

Continued on the front page F term (reference) 2H025 AA00 AB16 AC04 AD03 BE00 BE10 CB17 CB52 CC20 4H006 AA01 AA02 AB76 AC41 BA66 BB11 BB17 BC10 BJ50 BN30 BP30 BT12 FC52 GN03 KA31 4H039 CA10 CA60 CG10

Claims (3)

[Claims] 1. A compound of the general formula (I) (Wherein R ₁ is an alkyl group having 1 to 6 carbon atoms or 5 carbon atoms)
Or the six-cycloalkyl group, R ₂ is C 1 -C
Represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms, R ₃ represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 or 6 carbon atoms, and m is an integer of 0 to 2 , N is an integer of 0 to 3, and when m is 2 or more, R ₂ may be mutually the same or different;
When n is 2 or more, R ₃ may be the same or different. Monoalkoxycarbonylmethylated trisphenols represented by). 2. A compound of the general formula (II) (Wherein R ₁ is an alkyl group having 1 to 6 carbon atoms or 5 carbon atoms)
Or the six-cycloalkyl group, R ₂ is C 1 -C
And m represents an integer of 0 to 2, and when m is 2 or more, R ₂ may be the same as or different from each other. In the presence of an acid catalyst, an alkoxycarbonylmethoxybenzaldehyde represented by the general formula (III) Wherein R ₃ is an alkyl group having 1 to 6 carbon atoms or 5 carbon atoms.
Or 6 cycloalkyl groups, n is an integer of 0 to 3, and when n is 2 or more, R ₃ may be the same or different. Wherein a phenol represented by the formula (I) is reacted: (Wherein R ₁ is an alkyl group having 1 to 6 carbon atoms or 5 carbon atoms)
Or the six-cycloalkyl group, R ₂ is C 1 -C
And m represents an integer of 0 to 2, n represents an integer of 0 to 3, and when m is 2 or more, R ₂ represents R ₃ may be the same or different, and when n is 2 or more, R ₃ may be the same or different. A method for producing a monoalkoxycarbonylmethylated trisphenol represented by the formula: 3. A compound of the general formula (II) (Wherein R ₁ is an alkyl group having 1 to 6 carbon atoms or 5 carbon atoms)
Or the six-cycloalkyl group, R ₂ is C 1 -C
And m represents an integer of 0 to 2, and when m is 2 or more, R ₂ may be the same as or different from each other. ) Alkoxycarbonylmethoxybenzaldehydes.