JPH03223866A - Resist material - Google Patents

Abstract

PURPOSE:To enhance light transmittance, heat resistance, and solution stability by forming a resist material with a heat-resistant resin composed of constituents each having a functional group chemically changeable and solubilizable in alkali by heating and constituents each imparting heat resistance to the resin, and a specified photosensitive compound. CONSTITUTION:The resist material comprises the heat-resistant resin composed of the constituents each having the functional group chemically changeable and solubilizable in alkali by heating under an atmosphere containing an acid and the constituent for imparting heat resistance to the resin,a nd the photosensitive material for generating the acid by exposure to light and represented by formula I, and a solvent for capable of dissolving both, and in formula I, each of Ro<1> and Ro<4> is 1 - 10 C straight, branched, or cyclic alkyl, 1 - 10 C haloalkyl, or the like, independent from each other; each of Ro<2> and Ro<3> is H, 1 - 10 C straight or branched alkyl, or the like, independent from each other; and each of A and B is independently carbonyl or sulfonyl or the like, thus permitting light transmittance, heat resistance, and solution stability to be enhanced.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a resist material used in the manufacture of semiconductor devices and the like. For details, see 400 yen as an exposure energy source.
nm or less light source, e.g. 365 nm 1-line light 30On-
The following relates to a resist material film when forming a positive pattern using far ultraviolet light 1, for example, 248.4 nm KrF excimer laser light.

[Conventional technology] In recent years, with the high density integration of semiconductor devices.

The light source of exposure equipment used for 81N processing, particularly photolithography, has increasingly shorter wavelengths, and KrF excimer laser (24g, 4nα) light is now being considered. However, a resist material suitable for this wavelength has not yet been found.

For example, MP2400 (
(Manufactured by Sibley), the novolac resin itself as a base polymer has a large surface absorption against exposure light and the photoreactivity of the naphthoquinone diazide compound as a photosensitizer is not good, so the batten shape after development is very poor and it cannot be used. do not have. In addition, as a resist material using KrF excimer laser light or far ultraviolet light as a light source, we use a resin with high transparency to light around 248.4 nm and a photosensitive compound -C-C-C having a II II group in the molecule. - resist materials have been developed that consist of (for example,
JP-A-64-80944; JP-A-1-15404
No. 8; JP-A-1-155339, etc.).

A pattern forming material made of a photosensitive compound and a resin having high light transmittance near 248.4 nm has also been developed.

, (For example, Japanese Patent Application Laid-Open No. 1-188852 N: Y,
Tan1 et al., 5PIE's 19895ynlpo,
1086-03 etc.). A pattern forming method using this resist material will be described using FIG. A resist material 5 is spin-coated on a semiconductor substrate] 7 to obtain a resist material film of 1.0 μm (FIG. 4(a)). Note that an oxide film, a conductive film, and an insulating film are often formed on the substrate 1. Next, 248.4 nm KrF excimer laser beam 3 and mask 4
(FIG. 4(b)). Finally, by performing development using a transparent alkaline developer (0.24% tetramethylammonium hydroxide aqueous solution), the exposed areas of the resist material 5 are dissolved and removed, forming the pattern 5.
a is obtained (Fig. 4(C)). This resist material film (1μ
Figure 5 shows the ultraviolet spectral curves before and after exposure. The transmittance of this resist material after exposure was as low as 40%, whereas the resin used had a thickness of 70% at a thickness of 1 μm, indicating that sufficient front color was not obtained. Further, as a result of pattern forming experiments, the aspect ratio of the pattern was about 70 degrees, and a sufficient pattern shape was not obtained. Furthermore, the γ characteristics of this resist material film (1 μm) are shown in FIG. 6, and when using a resist material containing a photosensitive compound having a resist group, the sensitivity for boat fishing is 100 to 300 IiIJ/cm.
2, and it is difficult to put it to practical use using KrF excimer laser light (248.4 nm), which has low energy efficiency despite its high output. In addition, in recent years, chemically amplified resist materials using acid generated during exposure as a medium have been proposed as a means of reducing the amount of exposure energy [f(,
Ito et al., Polym, Ej+g, Sci, vol. 23,
1012 (1983)], and various reports have been made regarding this. (For example, W, R, Brunsvol
d et al., 5PIE'51989 Sympo, 1086
-40; T, Neenan et al., 5PIE's 19
89Sympo, 1086-01) However, the resins used in these chemically amplified resist materials have a relatively large number of aromatic rings, so the 248.4n
There are problems such as insufficient light transmittance near m and poor heat resistance of the resin.

Regarding photosensitive compounds, for example, onium salts such as triphenylsulfonium tetrafluoroborate have poor solution stability and exhibit their original performance immediately after preparing resist materials, but on semiconductor manufacturing lines. It is said that it is difficult to put it into practical use, and
In the case of sulfonic acid ester of 6-cinitrobenzyl, stability as a compound is recognized, but 2-nitro-6-nitrotubenzaldehyde, which is produced by exposure to light, is a commonly used developer (tetramethylammonium hydroxide aqueous solution). ), problems such as scum remaining in the N layer and poor pattern shape occur after development. Also, tris(methanesulfonyloxy)
Benzene is not suitable as a photosensitive compound for chemically amplified resists because its sensitivity is lower than that of the photosensitive compounds described above.

[Problems to be Solved by the Invention] In the case of a resist material of 3, it is difficult to obtain a good pattern shape and a large amount of exposure energy is required because the photosensitive compound must be illuminated. In addition, chemically amplified resist materials cannot be used unless the light transmittance of the resin near 248.4 nm is improved or the heat resistance of the resin is improved, and at the same time, the amount of exposure energy is lower for photosensitive compounds. There is a need for properties such that the product can generate an acid, have solution stability, and dissolve the product in a developer.

[Objective of the Invention] The present invention was made in view of the above-mentioned situation, and therefore, it provides a resin that has high transmittance after exposure to one-line light, far ultraviolet light, such as KrF excimer laser light, and has heat resistance. It is an object of the present invention to provide a resist material comprising a photosensitive compound that efficiently generates acid with high sensitivity (low exposure energy amount), is stable in solution, and is soluble in currently used developing solutions. purpose.

[Configuration of the Invention] In order to achieve the above object, the present invention consists of the following configuration.

"A heat-resistant resin consisting of a component having a functional group that undergoes a chemical change when heated in an acid atmosphere and becomes alkali-soluble, and a component that imparts heat resistance to the resin, and a heat-resistant resin that generates an acid upon exposure to light. A photosensitive compound represented by I];
A resist material comprising a solvent capable of dissolving both.

R [In the formula, R occupancy, Ra each represents a carbon number of 1 to IO
straight-chain bibranched or cyclic alkyl group, having 1 to 1 carbon atoms
0 haloalkyl group, linear or branched alkoxy group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, phenyl group, substituted phenyl group (substituents include halogen atoms,
A straight-chain seven-branched or cyclic alkyl group having 1 to 10 carbon atoms, a straight-chain or branched alkoxy group having 1 to 10 carbon atoms,
A haloalkyl group having 1 to 10 carbon atoms, 1. ~lO linear or branched alkylthio group, nitro group, nitrile group, or amide group) aralkyl group or substituted aralkyl group (substituent is a halogen atom, a linear or branched alkylthio group having 1 to 10 carbon atoms)
Branched or cyclic alkyl group, linear or branched alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to IO carbon atoms, linear or branched alkylthio having 1 to 10 carbon atoms group, nitro group, nitrile group or amide group), R6 and Ra each independently represent a hydrogen atom, a carbon number of 1 to 10
represents an alkyl group or a halogen atom, and A and B each independently represent a carbonyl group, a sulfonyl group, or a sulfinyl group. ]” The resist material of the present invention can reduce the amount of exposure energy as much as possible.
Chemical amplification is used to reduce a'.

That is, the resist material of the present invention contains a component having a functional group that undergoes a chemical change upon heating in an acid atmosphere generated from an acid generator upon exposure and becomes alkali-soluble, and a component that imparts heat resistance to the resin, i.e., a component that imparts heat resistance to the resin. On the other hand, it is characterized by the combined use of a heat-resistant resin (hereinafter abbreviated as Resin J according to the present invention) consisting of a component that has the function of suppressing the softening of the entire resin and a novel photosensitive compound. This is a new resist material with The component having a functional group that becomes alkali-soluble by heating in an acidic atmosphere (hereinafter abbreviated as "component having a specific functional group") according to the present invention includes, for example, P- Examples include monomers such as hydroxystyrene derivatives and P-hydroxy-α-methylstyrene derivatives. Specific examples include P-methoxystyrene, ρ-impropoxystyrene,
p-ter monobutoxystyrene, ρ-methoxymethoxystyrene 22-isopropoxymethoxystyrene, P
-tetrahydropyranyloxystyrene, P-tetrahydrofuranyloxystyrene, P-trimethylsilyloxystyrene, p-tert-butoxycarbonyloxystyrene, P-isopropoxycarbonyloxystyrene, or similar protection as P-hydroxystyrene derivatives. Examples include, but are not limited to, P-hydroxy-α-methylstyrene derivatives having a group. In addition, as a component that imparts heat resistance to the resin, the use of this component allows the entire resin to be heated to a temperature of 100°C or higher.
More preferably, any material can be used as long as it can prevent softening even when heated to 140'C or more, but examples include P-hydroxystyrene, P-chlorostyrene, styrene, α-methylstyrene, fumaronitrile, and monomaleic acid. Isopropyl, monomer she-butyl maleate,
Di-tert-butyl maleate, monocyclohexyl maleate, maleic anhydride, N-phenylmaleimide,
N-substituted phenylmaleimide, N-methylmaleimide,
Monomers such as N-n-butylmaleimide are more common.

For example, the resin according to the present invention has the following formula: [ [m] can cause hail.

[In the formula, R1 is a methyl group, an isopropyl group, a tert
Butyl group, methoxymethyl group, isopropoxymethyl group, tetrahydropyranyl group, tetrahydrofuranyl group,
represents a trimethylsilyl group, tert, -butoxycarbonyl group or isoproboxycarbonyl group, R2 represents a hydrogen atom, a halogen atom or a methyl group, R3 represents a hydrogen atom, a P-hydroxyphenyl group, a P-chlorophenyl group, Phenyl group, cyano group or -COOR7 (however,
R7 is a branched or cyclic alkyl group having 3 to 1 carbon atoms,
Or represents a hydrogen atom.

), and R4 and R6 are each independently a hydrogen atom.

Represents a methyl group or a halogen atom, R6 is a hydrogen atom,
Cyano group or -COOR8 (However, R8 has 3 to 1 carbon atoms
0 branched or cyclic alkyl group, or a hydrogen atom. ), R9 is a hydrogen atom or -COOR'0(
However, RIO represents a branched or cyclic alkyl group having 3 to 10 carbon atoms, or a hydrogen atom. ), k and l
each independently represents a natural number. [wherein, represents a phenyl group, q represents O or a natural number), 1' and P each independently represent 0 or a natural number, R1, R2, H3, Ra,
R5, H6, R9 and k are the same as above. These compounds represented by the formula [■ or [m] are:
Although these compounds are representative of the resins according to the present invention, the resins according to the present invention are of course not limited to these compounds.

Specific examples of the resin according to the present invention include P-impropoxystyrene and α-methylstyrene copolymers, P-impropoxystyrene and α-methylstyrene copolymers,
Tetrahydropyranyloxystyrene and P-hydroxystyrene copolymer, p-tert-butoxystyrene and P-hydroxystyrene copolymer.

p-tert-butoxycarbonyloxystyrene and maleic acid monocyclohexyl ester copolymer, p-t
ert-butoxycarbonyloxystyrene and α-methylstyrene copolymer, p-tert-butoxystyrene and fumaronitrile copolymer, P-methoxymethoxystyrene and P-chlorostyrene copolymer, P-methoxymethoxystyrene and monocyclohexyl maleate Copolymer with ester and maleic anhydride, P-tetrahydrofuranyloxystyrene and N-methylmaleimide copolymer, p
-tert-butoxycarbonyloxystyrene and P-
copolymer with hydroxystyrene and maleic anhydride,
Copolymer of P-tetrahydropyranyloxystyrene, P-hydroxystyrene and fumaronitrile, p-t
A copolymer of ert-butoxycarbonyloxystyrene, P-hydroxystyrene and N-butylmaleimide.

Examples include, but are not limited to, copolymers of ρ-tetrahydropyranyloxystyrene, P-hydroxystyrene, and N-phenylmaleimide.

The fM resin according to the present invention is produced by a copolymer production method in which one or more components (monomers) having the above-mentioned specific functional groups and one or more components (monomers) that impart heat resistance to the resin are combined. It can be easily obtained by copolymerization according to a conventional method. That is, one or more components (monomers) having the above-mentioned specific functional group and one or more components (monomers) that impart heat resistance to the resin are combined with, for example, benzene,
In an organic solvent such as toluene, a radical polymerization initiator [e.g. azobisisobutyronitrile 2,2'-azobis(2
, 4-dimethylvaleronitrile), 2,2'-azobis(methyl 2-methylpropionate) and peroxide polymerization initiators such as benzoyl peroxide and lauroyl peroxide]. 50-100°C in nitrogen stream in the presence of
The polymerization reaction may be carried out for 1 to 10 hours.

After the reaction, post-treatment may be performed and isolated according to a conventional method for obtaining a polymer compound.

It goes without saying that the resin according to the present invention can also be easily obtained by appropriately introducing the specific functional group into a commercially available polymer such as poly(P-vinylphenol) through a chemical reaction.

The weight average molecular weight (Mw) of the resin according to the present invention is usually 1
,000 to about 40,000, preferably 3,000
It is about ~20,000.

In the photosensitive compound represented by the general formula [I] used in the present invention, Ra, an alkyl group of a linear bibranched or cyclic alkyl group represented by Ra, an alkyl group of a haloalkyl group, and a straight chain Examples of the alkyl group of the shaped and branched alkoxy group include a methyl group, an ethyl group, a propyl group, a butyl group, and an amyl group.

Examples of the alkyl group having 1 to 10 carbon atoms such as hexyl group, octyl group, and decyl group include chlorine, bromine, fluorine, and iodine as the halogen of the haloalkyl group, and examples of the alkenyl group include vinyl group.

Topropenyl group, 2-propenyl group (allyl group).

Examples include alkenyl groups having carbon vI2 to IO such as 2-butenyl group, isopropenyl group, 1,3-butassie=zLJ, 4;, 2-pentenyl group, and 1-hexenyl group. As aralkyl Jλ, for example, benzyl group , phenethyl group.

Phenylpropyl group, phenylbutyl group, etc. 7 to 1 carbon atoms
．． 0 aralkyl groups are mentioned. In addition, the alkyl group of a linear hepta-branched or cyclic alkyl group that is a substituent of a substituted phenyl group and a substituted aralkyl group, the alkyl group of a linear or branched alkoxy group, the alkyl group of a haloalkyl group, As an alkyl group of a linear or branched alkylthio group.

For example, methyl Jk, ethyl group, propyl group, butyl group,
Examples include alkyl groups having 1 to 10 carbon atoms such as amyl group, hexyl group, octyl group, and decyl group, and examples of the halogen atom and the halogen of the haloalkyl group include chlorine, bromine, fluorine, and iodine. In addition, examples of the linear or branched alkyl group represented by RiotR4 include a methyl group,
Ethyl group, propyl group.

Butyl group, amyl group, hekynyl group, octyl group.

nine alkyl groups having 1 to 10 carbon atoms such as decyl group;

Halogen: Examples of zlN include chlorine, bromine, fluorine, and iodine.

As a result of extensive research into photosensitive compounds that generate acid upon exposure, the present inventors found that they are stable in solutions and soluble in currently used image solutions, as shown by the above-mentioned formula [I]. The inventors discovered a photosensitive compound and further discovered that when the photosensitive compound was used, the efficiency of acid generation upon exposure to light was high and the resolution was significantly improved, leading to the completion of the present invention.

The solvent used in the present invention may be any solvent that can dissolve both the resin and the photosensitive compound, but it is usually more preferable to use a solvent that does not have absorption near the 365nn and 248.4+ marks. It will be done. More specifically, examples include ethyl cellosolve acetate, methyl cellosolve acetate, diethylene glycol dimethyl ether, ethyl 7L acid, methyl 7L acid, dioxane, and ethylene glycol monoisopropyl ether, but the examples are of course not limited to these.

The resin according to the present invention absorbs light in the 0-wavelength region (more than 3,000 nm), and has extremely high light transient properties for one-line light of 365 nm. It has been confirmed that acid is generated, and a chemical amplification effect can be used. Therefore, the resist material of the present invention can be produced using a low exposure dose of K"F excimer laser light (248
-4 nm) or one-line light (365 nm).

[Function] To explain the function of the present invention using a specific example, first, a region exposed to KrF excimer laser light, i-line light, etc. generates acid according to the photoreaction shown in (A) below, for example.

When heat treatment is performed following the exposure step, the functional groups of the pA fat undergo a chemical change by the acid according to the reaction formula (B) below, becoming alkali-soluble and eluting into the developer during development.

On the other hand, since no acid is generated in the unexposed area, no chemical change occurs even after heat treatment, and no alkali-soluble groups are expressed. Furthermore, since the resin itself has high heat resistance, no softening of the resin is observed during heat treatment. When a pattern is formed using the resist material of the present invention as described above, a large difference in solubility in an alkaline developer occurs between exposed and unexposed areas.
Moreover, since the resin in the unexposed areas does not soften during the heat treatment, a positive pattern with good contrast is formed. Further, as shown in the reaction formula (B), since the acid generated by exposure acts catalytically, exposure only needs to generate the necessary acid, making it possible to reduce the amount of exposure energy.

[Example] The present invention will be explained in more detail by referring to Examples and Reference Examples below, but the present invention is not limited by these in any way.

Reference Example 1 88 g of p-tert-butoxystyrene and 39 g of fumaronitrile were mixed in a toluene solvent under a nitrogen stream in the presence of 2,2'-azobis(methyl 2-methylpropionate),
A polymerization reaction was carried out at 90°C for 2 hours. After the reaction, the reaction solution is poured into methanol to crystallize, and the precipitated product is measured at wave numbers.

After drying, 120 g of p-Lert-butoxystyrene-fumaronitrile copolymer (n about 10,000) was obtained.

Example 1゜ Regis consisting of the following composition p-tert-butoxystyrene fumaronitrile copolymer A sheet material was prepared.

Diethylene glycol dimethyl ether tS, Og 1st
A pattern forming method using the above resist material will be explained with reference to the drawings. The resist material 2 was spin-coated onto a substrate 1 such as a semiconductor, and after soft baking on a hot plate at 90° C. for 90 seconds, a resist material film with a thickness of 1.0 μm was obtained (FIG. 1(a)). Next, 248.4 nm KrF excimer laser light 3 was selectively exposed through a mask 4 (
Figure 1(b)). After baking on a hot plate at 130°C for 90 seconds, developing with an alkaline developer (2.38% tetramethylammonium hydroxide aqueous solution) for 60 seconds dissolves and removes only the exposed areas of resist material 2, forming a positive pattern. 2a was obtained (Figure 1 (C)). Figure 2 shows the UV spectral curves of this resist material g (1 μm) before and after exposure. Before exposure, the transmittance was about 55%, and after exposure it was about 48%. % transmittance. Also, the aspect ratio of the positive pattern at this time is about 88 degrees, which is like a light shadow.
．． 30μ0 line and space, < turn.

Furthermore, the γ characteristics of this resist material film (1 μm) are shown in FIG. This material had a high sensitivity with a minimum exposure dose of 4 mJl-2.

Example 2゜In Example 1, the resin was changed to the styrene resin shown below, a resist material was prepared in the same manner as in Example 1, and the same experiment as in Example 1 was conducted. -tert-butoxystyrene- p-hydroxystyrene copolymer (9 about 13,000)
As a result, the same good results as in Example 1 were obtained.

The positive number of turns obtained using this resist material is approximately 3
It was possible to form many turns with this exposure energy amount of nJ/am.

Example 3 A resist material was prepared in the same manner as in Example 1 except that the photosensitive compound in Example 1 was changed to the compound shown below, and the same experiment as in Example 1 was conducted.

As a result, good results similar to those of Example 1 were obtained. The positive pattern obtained using this resist material is approximately 3Il.
Pattern formation was possible with an exposure energy amount of 112 lJ/cI.

Example 4゜The photosensitive compound in Example 2 was changed to the compound shown below, and the resist material was changed to m in the same manner as in Example 2 except for the following.
The same experiment as in Example 2 was conducted.

As a result, good results similar to those of Example 2 were obtained. The positive pattern obtained using this resist material was approximately 2 mJ.
Pattern formation was possible with an exposure energy amount of /cm2.

Example 5 p-tert-butoxycarbonyloxystyrene maleic acid copolymer (M-about 9,000) (k/1/
p=2/1/1) 6.0g Ethylene glycol monoisopropyl ether 15.0
g Example 1 using resist material prepared with the above composition
A similar experiment was conducted.

As a result, good results similar to those of Example 1 were obtained. The positive pattern obtained using this resist material is approximately 8 mJ
Pattern formation was possible with an exposure energy amount of /an2.

[Effects of the Invention] The resist material according to the present invention can be used with a light source of 40 Or+m or less, such as 365 nm i-line light, 300 nm or less deep ultraviolet light (
Deep UV) - for example, KrF excimer laser light (24
When used as a resist material for exposure such as 8° 4 nm), fine patterns with good shapes on the order of submicrons can be easily obtained. Therefore, the present invention has great value for the formation of ultra-fine patterns in the semiconductor industry and the like.

This resist material is particularly effective with i-line light, far ultraviolet light, and KrF excimer laser light, but it can also be used satisfactorily with electron beams and X-rays.

[Brief explanation of drawings]

Figures 1 to 3 show the results obtained in Example 1;
The figure is a process cross-sectional view of a pattern forming method using the resist material of the present invention.
The figures show γ characteristic diagrams of the resist materials of the present invention. Fig. 4 is a process cross-sectional view of a pattern forming method using a conventional resist material, Fig. 5 is an ultraviolet ray spectral curve diagram of a conventional resist material (the solid line is before exposure, the broken line is after exposure), and Fig.
The figure is a γ characteristic diagram of a conventional resist material. DESCRIPTION OF SYMBOLS 1...Substrate, 2...Resist material film of the present invention, 3.
...KrF excimer laser light, 4...mask, 5...
- Conventional resist material film, 2a...resin pattern.

Claims (3)

[Claims] (1) A heat-resistant resin consisting of a component that has a functional group that undergoes a chemical change when heated in an acid atmosphere and becomes alkali-soluble, and a component that imparts heat resistance to the resin, and the following general resins that generate acid when exposed to light: A resist material comprising a photosensitive compound represented by formula [I] and a solvent capable of dissolving both. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] [In the formula, R_0^1 and R_0^4 each independently represent a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, or a carbon number Haloalkyl group having 1 to 10 carbon atoms, linear or branched alkoxy group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, phenyl group, substituted phenyl group (substituents include halogen atom, carbon number 1 ~10 straight chain, branched or cyclic alkyl group, straight chain or branched alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, 1 to 10 carbon atoms
10 linear or branched alkylthio groups, nitro groups,
nitrile group or amide group), aralkyl group or substituted aralkyl group (substituent is a halogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, 1 to 10 carbon atoms)
straight-chain or branched alkoxy group, haloalkyl group having 1 to 10 carbon atoms, straight-chain or branched alkylthio group having 1 to 10 carbon atoms, nitro group, nitrile group, or amide group)
, R_0^2 and R_0^3 each independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or a halogen atom, and A and B each independently represent a carbonyl group. , represents a sulfonyl group or a sulfinyl group. ] (2) A heat-resistant resin composed of a component having a functional group that undergoes a chemical change upon heating in an acid atmosphere and becomes alkali-soluble, and a component that imparts heat resistance to the resin has the following general formula [
II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[II] [In the formula, R^1 is a methyl group, isopropyl group, tert
- represents a butyl group, methoxymethyl group, isopropoxymethyl group, tetrahydropyranyl group, tetrahydrofuranyl group, trimethylsilyl group, tert-butoxycarbonyl group or isopropoxycarbonyl group, and R^2 is a hydrogen atom, a halogen atom or a methyl group represents R^3
is a hydrogen atom, p-hydroxyphenyl group, p-chlorophenyl group, phenyl group, cyano group is -COOR^7(
However, R^7 represents a branched or cyclic alkyl group having 3 to 10 carbon atoms, or a hydrogen atom. ), R^4 and R^6 each independently represent a hydrogen atom, a methyl group, or a halogen atom, and R^5 is a hydrogen atom, a cyano group, or -COOR^8 (however, R^8 is the number of carbon atoms 3 to 10 branched or cyclic alkyl groups, or a hydrogen atom), and R^9 is a hydrogen atom or -CO
OR^1^0 (However, R^1^0 represents a branched or cyclic alkyl group having 3 to 10 carbon atoms, or a hydrogen atom.)
, and k and l each independently represent a natural number. ]
The resist material according to claim 1, which is a resin represented by: (3) A heat-resistant resin composed of a component having a functional group that undergoes a chemical change upon heating in an acid atmosphere and becomes alkali-soluble and a component that imparts heat resistance to the resin has the following general formula [
III] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[III] [In the formula, X is an oxygen atom or N-(CH_2)_q-R^
1^1 (However, R^1^1 is a straight chain with 1 to 10 carbon atoms,
It represents a branched or cyclic alkyl group or a phenyl group which may have a substituent, and q represents 0 or a natural number. ), l' and P each independently represent 0 or a natural number, R^1, R^2, R^3, R^4, R^5, R
^6, R^9 and k are the same as above. ] The resist material according to claim (1), which is a resin represented by: