JPH08106160A - Radiation sensitive resin composition - Google Patents

Abstract

PURPOSE: To obtain a radiation sensitive resin compsn. capable of effectively suppressing the occurrence of scum, excellent in developability, having high resolution and excellent in heat resistance by incorporating a specified phenol compd., an alkali-soluble resin and a 1,2-quinonediazido compd. CONSTITUTION: This radiation sensitive resin compsn. contains a phenol compd. represented by the formula, an alkali-soluble resin and a 1,2-quinonediazido compd. In the formula, each of R1 and R2 is H, alkyl, alkoxyl or hydroxyl and each of (m) and (n) is an integer of 0-3. The alkali-soluble resin is, e.g. novolak resin, polyvinyl phenol, its deriv., a styrene-maleic an hydride copolymer, polyvinyl hydroxybenzoate or methacrylic acid resin having carboxyl groups.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a radiation-sensitive resin composition containing an alkali-soluble resin and a 1,2-quinonediazide compound. More specifically, it relates to a radiation-sensitive resin composition suitable as a resist for producing highly integrated circuits, which is sensitive to radiation such as ultraviolet rays, far ultraviolet rays, X-rays, electron beams, molecular beams, γ rays, synchrotron radiation, and proton beams.

[0002]

2. Description of the Related Art Positive resists are often used in the manufacture of integrated circuits because a resist pattern of high resolution can be obtained. However, with the high integration of integrated circuits in recent years, resists with higher resolution have been obtained. A positive resist capable of forming a pattern is desired. Generally, as a method of improving the resolution of a positive resist, there is a method of reducing the molecular weight of an alkali-soluble resin contained therein, but there is a problem that the heat resistance of the resist is lowered. Further, it is possible to increase the addition amount of the quinonediazide compound, however, when the addition amount of the quinonediazide compound increases, the developability deteriorates,
If one performance is improved, the other performance is degraded. Therefore, a positive resist having high resolution, heat resistance, and good developability with a fine pattern is desired.

Japanese Patent Laid-Open No. 3-179353 discloses the following formula

[0004]

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[In the formula, R is an alkyl group or an alkoxyl group, and n is a number of 0 or more and 3 or less. ] A positive type radiation sensitive resist composition containing an alkali-soluble resin containing a phenol compound represented by the above formula and a 1,2-quinonediazide compound is disclosed.

Further, in Japanese Patent Laid-Open No. 4-1650, the following formula

[0007]

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[In the formula, A is an alkylene group, a substituted alkylene group, an alkenylene group, a substituted alkenylene group, an arylene group or a substituted arylene group, and R _{1 to} R ₈ are the same or different, and are hydrogen, halogen and C ₁ to C. ₄ alkyl groups, C ₁ -C ₄ alkoxyl groups, C ₂ -C ₄ alkenyl groups or hydroxyl groups. ] A positive resist composition containing a compound represented by the formula [1], an alkali-soluble phenol resin, and a quinonediazide sulfonic acid ester-based photosensitizer is disclosed. However, with these positive resist compositions, the sensitivity, resolution, developability and heat resistance are well balanced, and compositions excellent in their respective properties have not been obtained.

[0009]

SUMMARY OF THE INVENTION An object of the present invention is to provide a new radiation sensitive resin composition. Another object of the present invention is to provide a radiation-sensitive resin composition suitable as a positive resist, in which generation of scum is effectively suppressed, development is excellent, high resolution is obtained, and heat resistance is excellent. It is in. Further objects and advantages of the present invention will be apparent from the following description.

[0010]

According to the present invention, the above objects and advantages of the present invention are achieved by the following general formula (1):

[0011]

[Chemical 4]

[In the formula (1), R ₁ and R ₂ are the same or different from each other and represent a hydrogen atom, an alkyl group, an alkoxyl group or a hydroxyl group, and m and n are 0,
Which is an integer of 1, 2 or 3], a radiation-sensitive resin composition containing a phenol compound, an alkali-soluble resin and a 1,2-quinonediazide compound.

The present invention will be specifically described below, but the purpose, constitution and effect of the present invention will be clarified by this.

Alkali-Soluble Resin The alkali-soluble resin used in the present invention (hereinafter,
It is called "resin (A)". Examples of) include novolac resins, polyvinylphenol or its derivatives, styrene-maleic anhydride copolymers, polyvinylhydroxybenzoates, and carboxyl group-containing methacrylic acid resins.

As the resin (A), the resins represented by the above examples can be used alone or in combination of two or more kinds.

As a preferred resin (A), a novolac resin can be mentioned. Such novolac resin has the following formula (2)

[0017]

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It can be obtained by polycondensing a phenol represented by the formula (2) is an integer of 1 to 3 and an aldehyde represented by a monoaldehyde compound or a bisaldehyde compound.

Examples of the above-mentioned phenols include o-cresol, m-cresol, p-cresol and 2,3-
Examples thereof include xylenol, 2,5-xylenol, 3,4-xylenol, 3,5-xylenol, 2,3,5-trimethylphenol and 3,4,5-trimethylphenol. In particular o-cresol, m-cresol,
P-cresol, 2,3-xylenol, 2,5-xylenol, 3,4-xylenol, 3,5-xylenol and 2,3,5-trimethylphenol are preferred. These phenols may be used alone or in combination of two or more. In this case, m-cresol / 2,3-xylenol / 3,4-xylenol = 20 to 95/5
80/0 to 75 (weight ratio), or m-cresol /
A combination of 2,3,5-trimethylphenol / 2,3-xylenol = 20 to 95/5 to 80/0 to 75 (weight ratio) is particularly preferable.

Examples of monoaldehydes to be polycondensed with the above-mentioned phenols include formaldehyde, trioxane, paraformaldehyde, benzaldehyde, acetaldehyde, propylaldehyde, phenylacetaldehyde, α-phenylpropylaldehyde,
β-phenylpropyl aldehyde, o-hydroxybenzaldehyde, m-hydroxybenzaldehyde, p-
Hydroxybenzaldehyde, o-chlorobenzaldehyde, m-chlorobenzaldehyde, p-chlorobenzaldehyde, o-nitrobenzaldehyde, m-nitrobenzaldehyde, p-nitrobenzaldehyde, o-
Examples thereof include methylbenzaldehyde, m-methylbenzaldehyde, p-methylbenzaldehyde, p-ethylbenzaldehyde, pn-butylbenzaldehyde and furfural. Examples of bisaldehydes include glyoxal, glutaraldehyde, terephthalaldehyde, isophthalaldehyde and the like. Of these, formaldehyde can be used particularly preferably.

As a formaldehyde source,
For example, formalin, trioxane, paraformaldehyde, methyl hemiformal, ethyl hemiformal, propyl hemiformal, butyl hemiformal, phenyl hemiformal, etc. can be mentioned. Of these, formalin and butyl hemiformal can be particularly preferably used.

These aldehydes can also be used alone or in combination of two or more kinds. The amount of the aldehyde used is preferably 0.7 to 3 mol, and more preferably 0.8 to 1.5 mol, per 1 mol of the phenol.

An acidic catalyst is usually used for the polycondensation reaction of phenols and aldehydes. Examples of the acidic catalyst include hydrochloric acid, nitric acid, sulfuric acid, formic acid, oxalic acid, acetic acid and the like. The amount of these acidic catalysts used is usually 1 × 10 ^{−5 to} 5 per mol of phenols.
× 10 ^-1 mol.

In the polycondensation reaction, water is usually used as the reaction medium, but when the phenols used in the polycondensation reaction do not dissolve in the aqueous solution of aldehydes and become a heterogeneous system from the initial stage of the reaction, It is also possible to use hydrophilic solvents as reaction medium. As these hydrophilic solvents,
Examples thereof include alcohols such as methanol, ethanol, propanol and butanol; and cyclic ethers such as tetrahydrofuran and dioxane. The amount of these reaction media used is usually 20 to 100 parts by weight of the reaction raw material.
It is 1,000 parts by weight. The temperature of the polycondensation reaction can be appropriately adjusted depending on the reactivity of the reaction raw materials, but is usually 10 to 200 ° C. The method of the polycondensation reaction,
A method in which phenols, aldehydes, acidic catalysts and the like are charged all at once and a method in which phenols, aldehydes and the like are added in the presence of an acidic catalyst as the reaction progresses can be employed. After completion of the polycondensation reaction, in order to remove unreacted raw materials, acidic catalyst, reaction medium and the like existing in the system, generally, the temperature of the reaction system is raised to 130 to 230 ° C. and volatilized under reduced pressure. The fraction is distilled off and the novolak resin is recovered.

The polystyrene-equivalent weight average molecular weight (hereinafter referred to as "Mw") of the resin (A) used in the present invention is workability when the composition of the present invention is applied to a substrate and developability of the composition. , From the viewpoint of sensitivity and heat resistance,
2,000 to 20,000 is preferable, and 3,000 is preferable.
It is particularly preferable that it is ˜15,000.

In order to obtain a novolak resin having a high Mw, the novolak resin obtained by the above method is dissolved in a good solvent such as ethylene glycol monomethyl ether acetate, dioxane, methanol, ethyl acetate and then water. , A poor solvent such as n-hexane or n-heptane may be mixed, and the resin solution layer that is then precipitated may be separated to recover a high molecular weight novolak resin.

Phenol Compound The composition of the present invention contains the phenol compound represented by the above formula (1) (hereinafter referred to as “compound (a)”).

In the formula (1), R ¹ and R ² are the same or different from each other and represent a hydrogen atom, an alkyl group, an alkoxyl group or a hydroxyl group, and m and n are 0, 1,
Indicates an integer of 2 or 3.

Here, the alkyl group has 1 to 1 carbon atoms.
The alkyl group of 4 is preferable, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and a t-butyl group. Moreover, as the alkoxyl group, an alkoxyl group having 1 to 4 carbon atoms is preferable, and specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like.

Specific examples of the compound (a) include the following formulas (3-1) to (3-24).

[0031]

[Chemical 6]

[0032]

[Chemical 7]

[0033]

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In the composition of the present invention, the compound (a)
Is preferably used in an amount of 5 to 50 parts by weight, particularly 10 to 40 parts by weight, per 100 parts by weight of the resin (A). Further, the compound (a) can be used alone or in combination of two or more kinds.

In the present invention, a phenol compound other than the compound (a) (hereinafter referred to as "compound (b)") can be blended in combination with the compound (a). Examples of the compound (b) include a phenol compound having 2 to 6 benzene rings, a low molecular weight alkali-soluble novolac resin having Mw of 300 to 1,000, and the like. The compounding amount of the compound (b) or the low molecular weight alkali-soluble novolac resin is usually 50 parts by weight or less per 100 parts by weight of the resin (A).

1,2-Quinonediazide Compound Examples of the 1,2-quinonediazide compound used in the present invention include 1,2-benzoquinonediazide-4-sulfonic acid ester and 1,2-naphthoquinonediazide-4-.
Sulfonic acid ester, 1,2-naphthoquinonediazide-
Examples include 1,2-quinonediazide compounds such as 5-sulfonic acid ester. Such a 1,2-quinonediazide compound can be obtained by a known method, for example, by condensing a halogen compound of naphthoquinonediazidesulfonic acid and a phenol compound in the presence of a weak base. Here, examples of the phenol compound include 2,3,4-trihydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone, 2,3,4,2'4'-pentahydroxybenzophenone and tris ( 4-hydroxyphenyl) methane,
1,3,5-Tris (4-hydroxy-α, α-dimethylbenzyl) benzene, 1,1-bis (4-hydroxyphenyl) -1- [4- {1- (4-hydroxyphenyl) -1- Methylethyl} phenyl] ethane, 2-
(3,4-dihydroxyphenyl) -2- (4-hydroxyphenyl) propane, 2,4,4-trimethyl-2-
Examples thereof include compounds such as (2,4-dihydroxyphenyl) -7-hydroxychroman.

The compounding amount of the 1,2-quinonediazide compound other than the above is preferably 100 parts by weight or less with respect to 100 parts by weight of the resin (A).

Further, 1,2-occupying in the composition of the present invention
The total weight of the quinonediazide sulfonyl residue is adjusted to be 5 to 50% by weight, more preferably 10 to 30% by weight, based on the total solid content in the composition.

Various Compounding Agents The composition of the present invention may be compounded with various compounding agents such as a sensitizer and a surfactant, if necessary.

The sensitizer is added to improve the sensitivity of the resist. Examples of such a sensitizer include 2H-pyrido- [3,2-b] -1,4-oxazin-3 (4H) -ones and 10H-pyrido-.
Examples include [3,2-b]-(1,4) -benzothiazines, urazoles, hydantoins, parbituric acids, glycine anhydrides, 1-hydroxybenzotriazoles, alloxans, maleimides and the like. The blending amount of these sensitizers is preferably 50 parts by weight or less with respect to 100 parts by weight of the resin (A).

The surfactant is added to improve the coating property and developability of the composition. Examples of such a surfactant include polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene nonyl phenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, Megafac F171, F172, F1
73 (trade name, manufactured by Dainippon Ink and Chemicals, Inc.), Florard FC430, FC431 (trade name, manufactured by Sumitomo 3M Limited), Asahi Guard AG710, Surflon S-
382, SC-101, SC-102, SC-103,
SC-104, SC-105, SC-106 (trade name,
Asahi Glass Co., Ltd., KP341 (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow No. 75, no. 95 (trade name, manufactured by Kyoeisha Yushi Kagaku Kogyo Co., Ltd.). The compounding amount of these surfactants is 1% of solid content of the composition excluding various compounding agents.
Preferably, the active ingredient of the surfactant is 2 per 100 parts by weight.
It is less than or equal to parts by weight.

Further, in the composition of the present invention, a dye or a pigment can be blended in order to visualize the latent image on the radiation-irradiated portion of the resist and reduce the influence of halation during radiation irradiation, and also the adhesive property. In order to improve the above, an adhesion aid can be added. Further, if necessary, a storage stabilizer, a defoaming agent and the like can be added.

Solvent The composition of the present invention contains the above-mentioned resin (A), 1,2-quinonediazide compound and compound (a) and the above-mentioned various compounding agents optionally used, for example, a solid content concentration of 20 to It is prepared by dissolving it in a solvent so as to be 40% by weight and filtering it with a filter having a pore size of about 0.2 μm.

Examples of the solvent used at this time include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol methyl ether. acetate,
Propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclohexanone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, Examples thereof include methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, ethyl 3-methoxypropionate, methyl 3-methoxy-2-methylpropionate, ethyl acetate and butyl acetate. Furthermore, N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-
Methylacetamide, N, N-dimethylacetamide,
N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetonyl acetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, malein. Acid diethyl, γ-butyrolactone, ethylene carbonate,
It is also possible to add a high boiling point solvent such as propylene carbonate or phenyl cellosolve acetate. These solvents are used alone or in combination of two or more.

The composition of the present invention prepared as a solution for forming a resist film is applied to a silicon wafer or a wafer coated with aluminum by spin coating, cast coating, roll coating or the like. Next, this is prebaked to form a resist film, and the resist film is irradiated with radiation so as to form a desired resist pattern, and is developed with a developing solution to form a pattern.

The radiation used at this time is g-ray,
Ultraviolet rays such as i rays are preferably used, but far ultraviolet rays such as excimer laser, X rays such as synchrotron radiation, and various kinds of radiation such as charged particle beam such as electron beam can also be used.

Further, the composition of the present invention, after forming a resist film, prebaking and irradiating with radiation, 70 to 14
The effect of the present invention can be further improved by performing an operation of heating at 0 ° C. and then performing development.

The developer used for the resist film is, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate,
Ammonia water, ethylamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyldiethylamine, dimethylethanolamine, triethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, piperidine, 1 Alkaline compounds such as, 8-diazabicyclo- [5.4.0] -7-undecene and 1,5-diazabicyclo- [4.3.0] -5-nonene at a concentration of, for example, 1 to 10% by weight. An alkaline aqueous solution that is dissolved so as to be used is used. In addition, a water-soluble organic solvent, for example, alcohols such as methanol and ethanol, or a surfactant may be added to the developer in an appropriate amount. When a developer containing such an alkaline aqueous solution is used, it is generally washed with water after development.

[0049]

The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples. In addition, the measurement of Mw and the evaluation of the resist in the examples were performed by the following methods.

Mw: Tosoh GPC column (G200
0H _XL : 2 pieces, G3000H _XL : 1 piece, G4000
H _XL (1 bottle), flow rate: 1.0 ml / min, elution solvent: tetrahydrofuran, column temperature: 40 ° C., analysis conditions were determined by gel permeation chromatography using monodisperse polystyrene as a standard.

Resolution: The minimum size of a line-and-space pattern that is separated without reducing the film thickness by the exposure amount when resolving a 0.4-μm line-and-space pattern in a one-to-one relationship. It was measured at.

Developability: forming a resist film of the composition,
The scum after pattern formation and the degree of residual development were examined using a scanning electron microscope.

Heat resistance: The wafer on which the pattern was formed was heated in an oven for 2 minutes, and the temperature at which a 2.0 μm line-and-space pattern began to thermally deform was measured.

<Synthesis of Resin (A)> Synthesis Example 1 m-cresol 69.2 g (0.64 mol) 2,3-xylenol 9.8 g (0.08 mol) 3,4-xylenol 9. 8 g (0.08 mol) 37% by weight aqueous formaldehyde solution 61.0 g (formaldehyde: 0.75 mol) oxalic acid dihydrate 6.3 g (0.05 mol) Water 52.6 g and dioxane 182 g were charged and the autoclave was charged. Immerse in an oil bath and set the internal temperature to 130
After carrying out condensation for 8 hours while stirring at 80 ° C.,
After cooling to room temperature, the contents were taken out into a beaker. After separating into two layers in this beaker, the lower layer was taken out, concentrated, dehydrated and dried to recover the novolac resin. This resin is called resin (A1). The Mw of the resin (A1) was 8,600.

Synthesis Example 2 m-cresol 64.9 g (0.6 mol) 2,3-xylenol 36.7 g (0.3 mol) 3,4-xylenol 12.2 g (0.1 mol) 37 in an autoclave Weight% formaldehyde aqueous solution 77.1 g (formaldehyde: 0.9 mol) Oxalic acid dihydrate 6.3 g (0.05 mol) Water 79.4 g and dioxane 383.9 g were charged, and the autoclave was immersed in an oil bath. Temperature 130
After carrying out condensation for 8 hours while stirring at 80 ° C.,
After cooling to room temperature, the contents were taken out into a beaker. After separating into two layers in this beaker, the lower layer was taken out, concentrated, dehydrated and dried to recover the novolac resin. This resin is called resin (A2). The Mw of the resin (A2) was 7,800.

<Synthesis of 1,2-quinonediazide compound> Synthetic Example 3 14.6 g (0.05 mol) of tris (4-hydroxyphenyl) methane was added to a flask equipped with a stirrer, a dropping funnel and a thermometer in the dark. 3,2-naphthoquinonediazide-5-sulfonic acid chloride (33.5 g, 0.125 mol) and dioxane (248 g) were charged and dissolved with stirring. Then, the flask was immersed in a water bath controlled at 30 ° C., and the internal temperature was adjusted to 3
When the temperature became constant at 0 ° C, 13.9 g (0.138 mol) of triethylamine was slowly added dropwise to this solution using a dropping funnel so that the internal temperature did not exceed 35 ° C. Then, the precipitated triethylamine hydrochloride was removed by filtration, the filtrate was poured into a large amount of dilute hydrochloric acid to cause precipitation, and the precipitate was collected by filtration and dried in a heating vacuum dryer controlled at 40 ° C for a day and a night. -A quinonediazide compound (I) was obtained.

Synthesis Example 4 1,1-bis (4-hydroxyphenyl) -1- [4- {1- (4-hydroxyphenyl) -1-methylethyl} phenyl] ethane 21.2 g (0.05 mol) 1,2-naphthoquinonediazide-5-sulfonic acid chloride 26.8 g (0.1 mol) Triethylamine 11.1 g (0.11 mol) and dioxane 236 g were used in the same manner as in Synthesis Example 3, except that 236 g was used. A quinonediazide compound (II) was obtained.

Synthesis Example 5 2,3,4,4'-Tetrahydroxybenzophenone 24.6 g (0.10 mol) 1,2-naphthoquinonediazide-5-sulfonic acid chloride 80.6 g (0.30 mol) and triethylamine A 1,2-quinonediazide compound (c) was obtained in the same manner as in Synthesis Example 3 except that 33.3 g (0.33 mol) was used.

Examples 1 to 4 and Comparative Examples 1 to 4 At the composition ratios shown in Table 1 (where parts are parts by weight), resin (A), phenol compound (a) or compound (b), 1, A 2-quinonediazide compound and a solvent were mixed to form a uniform solution, which was then filtered through a membrane filter having a pore size of 0.2 μm to prepare a solution of the composition. The obtained solution was applied onto a silicon wafer having a silicon oxide film by using a spinner, and then prebaked on a hot plate at 90 ° C. for 2 minutes to form a resist film having a thickness of 1.1 μm. After that, through the reticle,
Nikon NSR-1755i7A reduction projection exposure machine (lens numerical aperture = 0.50) wavelength 365nm (i
Line), developed with a 2.38 wt% tetramethylammonium hydroxide aqueous solution, rinsed with ultrapure water and dried, then the performance of the composition was investigated. The results are shown in Table 1.

[0060]

[Table 1]

In Table 1, the types of phenol compounds and solvents other than those mentioned above are as follows. Phenol compound a-1: the above formula (3-1) a-2: the above formula (3-5) a-3: the above formula (3-7) α: 1,1,1-tris (4-hydroxyphenyl)
Ethane β: 1,1-bis (4-hydroxyphenyl) -1
-Phenylethane γ: Formula (4)

[0062]

[Chemical 9]

Solvent S1: Ethyl 2-hydroxypropionate S2: Ethyl 3-ethoxypropionate

The embodiments of the present invention will be summarized as follows. 1. A radiation-sensitive resin composition containing a phenol compound represented by the above formula (1), an alkali-soluble resin, and a 1,2-quinonediazide compound. 2. The radiation-sensitive material according to 1 above, wherein the alkali-soluble resin is selected from the group consisting of novolac resins, polyvinylphenol or its derivatives, styrene-maleic anhydride copolymers, polyvinylhydroxybenzoates and carboxyl group-containing methacrylic acid resins. Resin composition. 3. The radiation-sensitive resin composition as described in 1 above, wherein the phenol compound represented by the formula (1) is a compound represented by the formulas (3-1) to (3-24). 4. The radiation-sensitive resin composition as described in 1 above, which contains the phenol compound represented by the formula (1) in an amount of 5 to 50 parts by weight per 100 parts by weight of the alkali-soluble resin. 5. The 1,2-quinonediazide compound is one of the phenols,
2-benzoquinonediazide-4-sulfonic acid ester,
The feeling according to 1 above selected from the group consisting of 1,2-naphthoquinonediazide-4-sulfonic acid ester, 1,2-naphthoquinonediazide-5-sulfonic acid ester and 1,2-naphthoquinonediazide-6-sulfonic acid ester. Radioactive resin composition. 6. The radiation-sensitive resin composition as described in 1 above, which contains the 1,2-naphthoquinonediazide compound in an amount of 100 parts by weight or less per 100 parts by weight of the alkali-soluble resin.

[0065]

The radiation-sensitive resin composition of the present invention has excellent developability, high resolution and improved heat resistance. Therefore, the radiation-sensitive resin composition can be suitably used as a resist for producing an integrated circuit having a high degree of integration.

 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Toshiyuki Ota 2-11-24 Tsukiji, Chuo-ku, Tokyo Within Nippon Synthetic Rubber Co., Ltd. (72) Inventor Akira Tsuji 2-11-24 Tsukiji, Chuo-ku, Tokyo Within Nippon Synthetic Rubber Co., Ltd.

Claims (1)

[Claims] 1. The following general formula (1): [In the formula (1), R ₁ and R ₂ are the same or different from each other and represent a hydrogen atom, an alkyl group, an alkoxyl group or a hydroxyl group, and m and n are 0, 1, 2 or 3
The radiation-sensitive resin composition comprises a phenol compound, an alkali-soluble resin, and a 1,2-quinonediazide compound.