JP2003002883A - (Meth) acrylate compound having lactone structure, polymer thereof, resist material and pattern forming method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polymer material for a resist material excellent in all of adhesiveness, transparency and etching resistance in photolithography using a wavelength of 300 nm or less, particularly an ArF excimer laser beam as a light source. , A polymer thereof, a resist material containing the polymer as a base resin, and a pattern forming method using the resist material. SOLUTION: A (meth) acrylate compound represented by the following general formula (1). Embedded image (In the formula, R ¹ represents a hydrogen atom or a methyl group.)

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to (1) a novel (meth) acrylate compound useful as a monomer for a base resin of a resist material suitable for microfabrication technology, and (2)
The present invention relates to polymers using them as raw materials, (3) a resist material containing the polymer, and (4) a pattern forming method using the resist material.

[0002]

2. Description of the Related Art In recent years, with the high integration and high speed of LSIs, finer pattern rules are required, and far-ultraviolet lithography is regarded as a promising next-generation fine processing technique. Among them, KrF excimer laser light, A
Photolithography using rF excimer laser light as a light source is strongly desired to be realized as an indispensable technique for ultrafine processing of 0.3 μm or less. Excimer laser light,
Especially for resist materials used in photolithography using ArF excimer laser light having a wavelength of 193 nm as a light source, it is natural to ensure high transparency at the wavelength, high etching resistance that can correspond to thinning, and expensive optics. It is required to have high sensitivity that does not impose a burden on the system material and, above all, high resolution capable of accurately forming a fine pattern. In order to meet these requirements, it is necessary to develop a highly transparent, highly rigid and highly reactive base resin, but currently known polymer compounds have all of these properties. At present, there is no such thing, and a resist material suitable for practical use has not yet been obtained.

As the highly transparent resin, a copolymer of acrylic acid or methacrylic acid derivative, a polymer compound containing an alicyclic compound derived from a norbornene derivative in its main chain, and the like are known. Not satisfactory. For example, a copolymer of acrylic acid or methacrylic acid derivative is relatively easy to increase the reactivity because it is possible to introduce highly reactive monomers and increase the amount of acid labile units, but it is structurally rigid due to the structure of the main chain. Is extremely difficult to raise. On the other hand, for a polymer compound containing an aliphatic cyclic compound in the main chain, although the rigidity is within the allowable range, the structure of the main chain is less reactive with acid than poly (meth) acrylate, and the polymerization Since the degree of freedom is low, the reactivity cannot be easily increased. In addition, since the main chain has a high hydrophobicity, it has a drawback that the adhesion is poor when it is applied to a substrate. Therefore, when a resist material is prepared by using these polymer compounds as a base resin, even if the sensitivity and resolution are sufficient, it cannot withstand etching, or has low sensitivity even if it has an acceptable etching resistance, It results in low resolution and impracticality.

[0004]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and has a wavelength of 300 nm or less, particularly ArF.
In photolithography using an excimer laser light as a light source, a monomer that is a raw material of a polymer for a resist material having excellent adhesion, transparency, and etching resistance,
An object of the present invention is to provide the polymer, a resist material containing the polymer as a base resin, and a pattern forming method using the resist material.

[0005]

Means for Solving the Problems The inventor has conducted extensive studies in order to achieve the above object, and as a result, by the method described below,
A (meth) acrylate compound having a lactone structure represented by the following general formula (1) can be easily obtained in a high yield, and a resin obtained by polymerizing the (meth) acrylate compound has an exposure wavelength of an excimer laser. It was found that the resist material having a high transparency and a base material using the same has excellent substrate adhesion and etching resistance.

The present invention provides the following (meth) acrylate compound, a polymer thereof, a resist material and a pattern forming method. That is, it is composed of the following 1 to 6. 1. A (meth) acrylate compound represented by the following general formula (1).

[0007]

[Chemical 4] (In the formula, R ¹ represents a hydrogen atom or a methyl group.)

2. A polymer of a (meth) acrylate compound represented by the general formula (1), which is represented by the following general formula (1
A polymer containing the repeating unit represented by a) and having a weight average molecular weight of 2,000 to 100,000.

[Chemical 5] 3. Further, the polymer according to item 2 above, which contains a repeating unit represented by the general formula (2a).

[0009]

[Chemical 6] (In the formula, R ¹ represents a hydrogen atom or a methyl group, and R ² represents a tertiary alkyl group having 4 to 20 carbon atoms.)

4. A resist material comprising the polymer as described in 2 or 3 above. 5. A resist material containing (A) the polymer according to the above 2 or 3, (B) an acid generator, and (C) an organic solvent. 6. (1) A step of applying the resist material according to the above 4 or 5 on a substrate, (2) Then, after heat treatment, a step of exposing with a high energy beam or an electron beam having a wavelength of 300 nm or less through a photomask, ( 3) A pattern forming method, which comprises a step of performing a heat treatment if necessary and then developing with a developing solution.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.
The (meth) acrylate compound having a lactone structure of the present invention is represented by the above general formula (1), which can be produced, for example, by the following three-step synthetic method, but the present invention is not limited to this method. Not a thing. The details will be described below.

First, the first-step reaction is a lactone-forming reaction represented by the following (Chemical Formula 7), which is represented by the formula (3): 5-norbornene-2,3-dicarboxylic acid or the formula (4). 5-norbornene-2,3-dicarboxylic acid anhydride obtained by the reaction of the formula (5)
A carboxylic acid having a lactone structure represented by

[0013]

[Chemical 7]

Examples of the acid catalyst used in the lactone forming reaction represented by the chemical formula (7) are inorganic acids such as sulfuric acid, nitric acid, hydrochloric acid and salts thereof, formic acid, acetic acid, trifluoroacetic acid, p-
Examples thereof include organic acids such as toluenesulfonic acid and methanesulfonic acid, salts thereof, and cation exchange resins. The amount of the acid catalyst used is preferably 0.001 to 10 mol, and more preferably 0.01 to 2 mol per mol of the raw material. As the solvent used in the lactone forming reaction represented by the above (Chemical formula 7), organic acids such as acetic acid; hydrocarbons such as toluene, xylene, heptane; dibutyl ether,
Ethers such as diethylene glycol diethyl ether; chlorine-based solvents such as methylene chloride and 1,2-dichloroethane; water can be used alone or in admixture of two or more.

The reaction temperature for forming the lactone is preferably from room temperature to about the boiling point of the solvent, and an appropriate reaction temperature can be selected depending on the reaction conditions. For example, when sulfuric acid is used as the acid catalyst, 80 ° C to 120 ° C is particularly preferable. The reaction time of the lactone formation is preferably determined by tracking the progress of the reaction by thin layer chromatography, gas chromatography or the like for improving the yield, but it is usually about 1 to 20 hours. As a starting material, 5-norbornene-
When the 2,3-dicarboxylic acid anhydride (4) is used, it is necessary to add 1 mol or more of water to 1 mol of the raw material during the reaction because of hydrolysis of the acid anhydride. The reaction is carried out by heating and stirring under a nitrogen atmosphere. After the completion of the reaction, the carboxylic acid of the target product (5) is obtained by filtering and collecting the target product of the formula (5) precipitated during the usual aqueous work-up or during the reaction. The target product (5) can be purified by a conventional method such as recrystallization or chromatography, but usually has a sufficient purity for performing the next reaction as it is.

The reaction represented by the following (Chemical formula 8) in the second step is a reaction of reducing the carboxylic acid represented by the formula (5) to the alcohol represented by the formula (6). It can be carried out by acting a reducing agent on (5).

[0017]

[Chemical 8]

The reducing agent used in the second step reaction is
Metal hydrides such as diisobutylaluminum hydride; metal hydride complex compounds such as lithium aluminum hydride and sodium tetrahydroborate; borane, borane reagents such as borane-tetrahydrofuran complex, and the like are preferable, and particularly borane in terms of yield. Reagents are preferred. The amount of reducing agent used depends on the type of reducing agent used,
For example, when a borane-tetrahydrofuran complex is used, it is preferably used in an amount of 0.5 to 5.0 mol, particularly 1.0 to 2.0 mol, based on 1 mol of the carboxylic acid as a raw material. As the solvent used in the second step reaction, ethers such as tetrahydrofuran, diethyl ether, dibutyl ether;
Hydrocarbons such as hexane, heptane, toluene, xylene, etc. can be exemplified, and selected from these alone or 2
A mixture of two or more species can be used. The reaction temperature in the second step varies depending on the reducing agent used, but is -78 ° C to 100 ° C.
It is preferable to carry out at a temperature of 0 ° C, particularly 0 ° C to 60 ° C. The reaction time in the second step is preferably determined by tracking the reaction by thin layer chromatography, gas chromatography or the like in order to improve the yield, but it is usually about 1 to 20 hours. After completion of the reaction, normal aqueous work-up (aqueous work-u
The target alcohol (6) can be taken out by p). The obtained alcohol (6) can be purified by a conventional method such as chromatography or recrystallization, if necessary.

The reaction of the third stage is shown below (Chemical Formula 9),
Is a (meth) acrylate reaction of alcohol (6),
Performed by a conventional method such as a method using (meth) acrylic acid chloride and a base, an acid-catalyzed esterification reaction using (meth) acrylic acid, and an esterification reaction using a dehydration condensation agent such as (meth) acrylic acid and dicyclohexylcarbodiimide. be able to. If necessary, the obtained (meth) acrylate compound (1) can be purified by a conventional method such as chromatography, distillation and recrystallization.

[0020]

[Chemical 9] (In the formula, R ¹ represents a hydrogen atom or a methyl group.)

The present invention uses the ester compound represented by the general formula (1) as a raw material, contains the repeating unit represented by the general formula (1a), and has a weight average molecular weight of 2,000 to 1.
There is provided a polymer characterized in that it is 0,000. Further, the polymer of the present invention, that is, the resist base polymer preferably contains the repeating unit represented by the general formula (2a). In the general formula (2a), R ¹ is a hydrogen atom or a methyl group. R ² is a tertiary alkyl group having 4 to 20 carbon atoms. Specific examples of the tertiary alkyl group having 4 to 20 carbon atoms of R ² include t-butyl group, t-pentyl group, 1-ethyl-1-methylpropyl group, triethylcarbinyl group, 1-methylcyclopentyl group, 1-ethylcyclopentyl group, 1-cyclopentylcyclopentyl group, 1-cyclohexylcyclopentyl group, 1-methylcyclohexyl group, 1-ethylcyclohexyl group, 1
-Cyclopentylcyclohexyl group, 1-cyclohexylcyclohexyl group, 2-methyl-2-norbornyl group,
2-ethyl-2-norbornyl group, 8-methyl-8-tricyclo [5.2.1.0 ^2,6 ] decyl group, 8-ethyl-8
Examples include -tricyclo [5.2.1.0 ^2,6 ] decyl group, 2-methyl-2-adamantyl group, 2-ethyl-2-adamantyl group, and 1-adamantyl-1-methylethyl group. Not limited to. By containing the repeating unit represented by the general formula (2a), a polymer which is decomposed by an acid and becomes soluble in an alkali is provided.

As the polymer of the present invention, the above-mentioned (1a),
In addition to the repeating unit (2a), in order to further improve the performance as a resist material, a repeating unit obtained from various compounds having a polymerizable carbon-carbon double bond as described below can be contained. . Examples of these are α, β-unsaturated carboxylic acids such as (meth) acrylic acid; α, β-unsaturated carboxylic esters such as (meth) acrylic acid ester, crotonic acid ester, and maleic acid ester; acrylonitrile, etc. Α, β-unsaturated nitriles; 5,6-dihydro-2H-pyran-2-
Α, β-unsaturated lactones such as ones; maleic anhydride, itaconic anhydride, maleimides, norbornene derivatives, tetracyclo [4.4.0.1 ^2,5 . 1 ^7,10 ] dodecene derivative, allyl ethers, vinyl ethers, vinyl esters and the like. The polymer of the present invention is produced by polymerizing the (meth) acrylate ester compound represented by the general formula (1) and the above-mentioned other polymerizable compound by a conventional method such as radical polymerization, anion polymerization or cationic polymerization. can do. The weight average molecular weight of the polymer of the present invention, that is, the resist base polymer is 2,000 to 1
It is necessary to set it to 0,000, and if it is less than 2,000, film forming property and resolution may be inferior.
If it exceeds, the resolution may be poor.

The component (B) acid generator used in the present invention is an acid generator capable of generating an acid upon irradiation with a high energy beam or electron beam of 300 nm or less, and the acid generator and the acid generators described above. Any acid generator may be used as long as the resist composition comprising the polymer of the present invention and an organic solvent is a uniform solution and can be uniformly coated and formed into a film. The acid generator may be used alone or in combination of two or more.

Examples of the acid generator which can be used in the present invention include, for example, triphenylsulfonium salt derivatives such as triphenylsulfonium trifluoromethanesulfonate; diphenyliodonium salt derivatives such as dipt-butyliodonium trifluoromethanesulfonate. And other various onium salts, alkyl sulfonic acids, dialkyl sulfonyl diazomethanes, disulfones, sulfonic acid imides and the like. The amount of the acid generator blended is preferably 0.2 to 50 parts, particularly 0.5 to 40 parts, based on 100 parts of the total base polymer. If the amount is too small, the sensitivity and resolution may be inferior, and if it exceeds 50 parts, the transmittance of the resist may be lowered and resolution may be inferior.

The organic solvent of the component (C) used in the present invention may be any organic solvent in which the acid generator, the base polymer and the like can be dissolved. Examples of such organic solvents include ketones such as cyclohexanone; alcohols such as 1-methoxy-2-propanol and 1-ethoxy-2-propanol; propylene glycol monomethyl ether, ethylene glycol monomethyl ether,
Ethers such as propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, diethylene glycol dimethyl ether; propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethyl lactate, butyl acetate, methyl 3-methoxypropionate, 3 Examples include esters such as ethyl ethoxypropionate; lactones such as γ-butyrolactone, which may be used alone or in admixture of two or more, but are not limited thereto. In the present invention, among these organic solvents, the solubility of the acid generator in the resist component is the best, diethylene glycol dimethyl ether and 1-ethoxy-2-propanol, ethyl lactate, propylene glycol monomethyl ether acetate which is a safety solvent. And mixed solvents thereof are preferably used.

The basic constituents of the resist composition of the present invention are the above-mentioned polymer, acid generator and organic solvent. If necessary, a dissolution inhibitor, an acidic compound, a basic compound,
Other components such as stabilizers, dyes and surfactants may be added.

A pattern can be formed by using the resist material of the present invention by employing a known lithography technique. For example, a film such as a silicon wafer can be formed by a method such as spin coating to form a film. 0.3-2.0
Apply so that it becomes μm, and apply this on a hot plate for 6
0 to 150 ° C., 1 to 10 minutes, preferably 80 to 130
Prebak at 1 ° C for 1 to 5 minutes. Then, a mask for forming a desired pattern is held over the resist film, and a high-energy ray such as deep ultraviolet ray, excimer laser, or X-ray or electron beam is exposed at an amount of 1 to 200 mJ / cm ² , preferably 10 to 100 mJ. After irradiating so as to be / cm ² , post exposure bake (PEB) is performed on a hot plate at 60 to 150 ° C for 1 to 5 minutes, preferably 80 to 130 ° C for 1 to 3 minutes. Further, 0.1 to 5%, preferably 2 to 3% of a developer of an aqueous alkali solution such as tetramethylammonium hydroxide (TMAH) is used.
3 minutes, preferably 0.5-2 minutes, dipping method,
Development is performed by a conventional method such as a paddle method or a spray method to form a target pattern on the substrate. The resist material of the present invention is most suitable for fine patterning by deep ultraviolet rays of 248 to 193 nm or excimer laser, X-rays and electron beams, among high energy rays. If the above range is out of the upper limit or the lower limit, the desired pattern may not be obtained.

[0028]

EXAMPLES The present invention will be described in more detail below with reference to Examples and Reference Examples, but the present invention is not limited to these Examples. [Example 1] 3-methacryloyloxymethyl-2,
Synthesis of 6-norbornane carbolactone [methacrylate in which R ¹ = methyl group in the general formula (1)].

[0029]

[Chemical 10]

5-norbornene represented by the formula (7)
50 g of 2,3-dicarboxylic anhydride and 200% of 30% sulfuric acid
The mixture of g was heated and stirred at 120 ° C. for 2 hours under a nitrogen atmosphere. The produced solid matter was separated by filtration, separated, washed with water and dried under reduced pressure to obtain 48 g of 2,6-norbornanecarbolactone-3-carboxylic acid represented by the formula (8). Obtained 2,
6-Norbornanecarbolactone-3-carboxylic acid 48
g in a mixture of 200 g of tetrahydrofuran and borane.
Tetrahydrofuran complex (1 molar tetrahydrofuran solution, 400 mL) was added and stirred for 10 hours. The reaction was stopped by adding saturated saline, the organic layer was separated, and dried over anhydrous sodium sulfate. The solvent was distilled off by concentration under reduced pressure to give 3-hydroxymethyl-2 represented by the formula (9),
44 g of 6-norbornanecarbolactone was obtained. 32 g of methacryloyl chloride was added to a mixture of 44 g of the obtained 3-hydroxymethyl-2,6-norbornanecarbolactone, 38 g of triethylamine and 200 mL of methylene chloride at 5 to 10 ° C, and the mixture was stirred for 2 hours. After the reaction was stopped by adding water, the mixture was extracted with ethyl acetate, the organic layer was washed with water, and concentrated under reduced pressure. Purification was performed by silica gel column chromatography to obtain 50 g of 3-methacryloyloxymethyl-2,6-norbornanecarbolactone represented by the formula (10). The yield of the target compound represented by the formula (10) based on 5-norbornene-2,3-dicarboxylic acid anhydride was 70%.

(Results of IR and NMR analysis) IR (KBr): ν = 2964, 2883, 1768,
1714, 1637, 1456, 1354, 1325,
1308, 1173, 1105, 1051, 1020,
^{995,976,947cm -1 1 H-NMR (270MHz} in CDCl 3): δ =
1.55-1.75 (3H, m), 1.84 (1H, d
d, J = 14.6, 3.0 Hz), 1.93 (3H, b
r. s), 2.40-2.55 (2H, m), 2.65.
(1H, dd, J = 14.3, 4.9 Hz), 3.25
(1H, m), 4.21 (1H, dd, J = 11.7,
8.8 Hz), 4.36 (1H, dd, J = 11.7,
6.3 Hz), 4.78 (1H, dd, J = 7.8,
4.9 Hz), 5.56 (1 H, m), 6.11 (1
H, br. s).

Example 2 Synthesis of 3-acryloyloxymethyl-2,6-norbornanecarbolactone [an acrylate in which R ¹ = hydrogen atom in the general formula (1)].

[Chemical 11]

3-Acryloyloxymethyl-2,6-norbornanecarbolactone represented by the formula (11) was synthesized by the same three-step reaction as in Example 1 except that 28 g of acryloyl chloride was used instead of methacryloyl chloride. . 5-norbornene of the compound represented by the formula (11)
The yield based on 2,3-dicarboxylic acid anhydride was 66%.

Example 3 Synthesis of a polymer represented by the following structural formula (12) (in the formula, x = 0.5, y = 0.5).

[Chemical 12]

Methacrylate obtained in Example 1 11.
8 g, 8-ethyl-8-tricyclo [5.2.1.
A mixture of 12.4 g of 0 ^2,6 ] decyl methacrylate, 60 mg of N, N′-azobisisobutyronitrile, and 100 mL of tetrahydrofuran was heated and stirred at 60 ° C. for 20 hours under a nitrogen atmosphere. After cooling down, vigorously stirred methanol 2
The reaction mixture was added dropwise to L, and the deposited precipitate was separated by filtration. The obtained solid was washed with methanol and dried under reduced pressure to obtain 13.3 g of a target polymer. Yield 55%. ¹ H-NMR
The copolymerization ratio was 50:50 from the integral ratio of the spectrum. The weight average molecular weight by GPC analysis was 10,200 in terms of polystyrene, and the dispersity (Mw / Mn) was 1.78.

Example 4 Synthesis of polymer represented by the following structural formula (13) (where x = 0.4, y = 0.5, z =
0.1).

[Chemical 13]

The same procedure as in Example 3 was repeated except that 9.5 g of the methacrylate obtained in Example 1, 12.4 g of 2-ethyl-2-adamantyl methacrylate and 1.3 g of 2-hydroxyethyl methacrylate were used as raw material monomers. The above polymer was obtained. Yield 52%. Mw = 11,000
0, Mw / Mn = 1.85.

Example 5 Formation of Resist Pattern Using Polymer Using the polymer obtained in Example 3, a resist composition having the following composition was prepared. (A) Base polymer (polymer obtained in Example 3) 8
0 part by weight, (B) triphenylsulfonium trifluoromethanesulfonate as an acid generator 1.0 part by weight,
(C) 480 parts by weight of propylene glycol monomethyl ether acetate as a solvent, (D) 0.08 parts by weight of other tributylamine. 0.2 μm of this resist composition
m Teflon (registered trademark) filter, and then spin-coated on a silicon wafer sprayed with hexamethyldisilazane at 90 ° C. for 40 seconds, followed by heat treatment at 110 ° C. for 90 seconds to give a thickness of 500 nm. Was formed. This is exposed with ArF excimer laser light and 1
After heat treatment at 10 ° C. for 90 seconds, it was cooled to 23 ° C., and immersion development was performed for 60 seconds at 23 ° C. using a 2.38% tetrahydroammonium hydroxide aqueous solution. Space pattern formed. When the developed wafer was observed by an SEM in the air, it was confirmed that a pattern of 0.17 μm was resolved without pattern peeling. Similarly, the resist performance of the polymer obtained in Example 4 was evaluated.
It was confirmed that the pattern of 8 μm was resolved without peeling. From this, it was found that the photoresist composition of the present invention had excellent substrate adhesion and resolution.

Example 6 Evaluation of Transparency of Polymer 1.0 g of the polymer obtained in Example 3 was mixed with cyclohexanone 6.
After being dissolved in 0 g, it was filtered using a 0.2 μm Teflon (registered trademark) filter. The obtained solution was spin-coated on a quartz substrate and heat-treated at 90 ° C. for 60 seconds to form a thin film having a thickness of 500 nm. When the transmittance of this thin film at 193 nm was measured using an ultraviolet-visible spectrophotometer, the transmittance was 80% per 500 nm. Similarly, the polymer obtained in Example 4 was also measured, and the transmittance was 82% per 500 nm. From these results, it was confirmed that the polymer of the present invention has sufficient transparency as a photoresist base polymer for excimer laser.

Example 7 Evaluation of Etching Resistance of Polymer After dissolving 2 g of the polymer obtained in Example 3 in 10 g of cyclohexanone, it was filtered using a 0.2 μm Teflon (registered trademark) filter. The obtained solution was spin-coated on a silicon wafer and heat-treated at 90 ° C. for 60 seconds to form a thin film having a thickness of 700 nm. Using a reactive ion etching device for this thin film,
The etching rate for CF ₄ gas was measured under the conditions of er 100 W, pressure 5 Pa, and gas flow rate 30 ml / min.
As a result, the etching rate (novolak resist 1.
The value normalized as 00) was 1.13. Similarly, the polymer obtained in Example 4 was also measured, and the etching rate was 1.05. On the other hand, for comparison, Kr
The measurement was also performed on poly (p-hydroxystyrene) used as a base polymer of F resist,
The etching rate was 1.20. From these results, it was confirmed that the polymer of the present invention has a slow etching rate with respect to CF ₄ gas and is excellent in dry etching resistance.

[0041]

As is apparent from the above description, the polymer of the present invention is excellent in transparency, particularly in the excimer laser exposure wavelength and the dry etching resistance, and further prepared by using the polymer of the present invention. The resist material described above is well sensitive to high-energy rays, has excellent resolution, and is useful for fine processing with electron beams or deep ultraviolet rays. Further, since it has excellent substrate adhesion, it can easily form a fine pattern perpendicular to the substrate, and is suitable as a fine pattern forming material for VLSI production. Therefore, the (meth) acrylate compound having a lactone structure of the present invention is very useful in improving both the resolution and etching resistance of the resist.

   ─────────────────────────────────────────────────── ─── Continued front page    F term (reference) 2H025 AA09 AA14 AB16 AC04 AC06                       AC08 AD03 BC13 BC34 BE00                       BE10 BG00 CB41 CB55                 4C037 AA02                 4J100 AL03Q AL04Q AL05Q AL08P                       AL08Q BA11P BC03Q BC04Q                       BC07Q BC08Q BC09Q BC53P                       CA01 CA03 CA04 DA01 JA38

Claims (7)

[Claims] 1. A (meth) acrylate compound represented by the following general formula (1). [Chemical 1] (In the formula, R ¹ represents a hydrogen atom or a methyl group.) 2. A weight average molecular weight of 2,000 to 100,0 containing a repeating unit represented by the following general formula (1a).
The polymer is 00. [Chemical 2] (In the formula, R ¹ represents a hydrogen atom or a methyl group.) 3. The polymer according to claim 2, further comprising a repeating unit represented by the following general formula (2a). [Chemical 3] (In the formula, R ¹ represents a hydrogen atom or a methyl group, and R ² represents a tertiary alkyl group having 4 to 20 carbon atoms.) 4. The polymer according to claim 3, wherein the repeating unit represented by the general formula (1a) has a mole fraction of at least 5%. 5. A resist material comprising the polymer according to any one of claims 2 to 4. 6. A resist material containing (A) the polymer according to any one of claims 2 to 4, (B) an acid generator, and (C) an organic solvent. 7. (1) A step of applying the resist material according to claim 5 or 6 onto a substrate, (2) Then, after heat treatment, a high energy beam or an electron beam having a wavelength of 300 nm or less through a photomask. And a step of (3) performing a heat treatment if necessary, and then developing with a developing solution.