JPH03223862A - 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, and the photosensitive material for generating the acid by exposure to light and represented by formula I in which each of Ro<1> - Ro<3> is H, halogen, straight, branched, or cyclic alkyl, or the like, independent from each other; each of Ro<4> and Ro<5> is as before ore haloalkyl; Xo is a carbon atom, or benzene or naphthalene ring; and (n) is an integer of 0 - 4, 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 manufacturing semiconductor devices and the like. For details, see 400 yen as an exposure energy source.
A light source below nmJ5, e.g. 365r+m i-line light, 30
Far ultraviolet light of 0 nm or less, for example 248.4 nm KrF
The present invention relates to a resist material for forming a positive pattern using excimer laser light or the like.

[Prior Art] In recent years, with the high density integration of semiconductor devices, the light sources of exposure equipment used for microfabrication, particularly photolithography, have become increasingly shorter in wavelength, and now KrF excimer lasers (
248,4r+r+) light is now being considered. However, a resist material suitable for this wavelength has not yet been found.

For example, - KrF excimer laser light is quite powerful.
400 (manufactured by Sibley), the pattern shape after development is very poor because the Novolank resin of the pace polymer itself has a large surface absorption against the exposure light and the photoreactivity of the naphthoquinone diazide compound of the photosensitizer is not good. Cannot be used. In addition, resist materials have been developed that use KrF excimer laser light or far ultraviolet light as a light source. (For example, JP-A No. 64-80944; JP-A No. 1-154048) Pattern forming materials made of a photosensitive compound and a resin having high light transmittance in the vicinity of 248.4 nm have also been developed. 1-18885
Publication No. 2; Y, Tan1 et al., 5PIE's 1989
Sympo, 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 1, and a thickness of 1.0μ is applied.
A resist material film of m is obtained (FIG. 4(a)). Note that an oxide film, a conductive film, and an insulating film are often formed on the substrate 1. Next, it is selectively exposed to a 248.4n KrF excimer laser beam 3 through a mask 4 (Fig. 4(b)).
). Finally, development is performed using an ordinary alkaline developer (0.24% tetramethylammonium hydroxide aqueous solution) to dissolve and remove the exposed areas of the resist material 5, thereby obtaining a pattern 5a (FIG. 4(C)). . The UV spectral curves of this resist material film (1 μm) before and after exposure are shown in the fifth column.
As shown in the figure. While the resin used is 70% at a thickness of 1 μm, the transmittance of this resist material after exposure is as low as 40%.
It can be seen that sufficient light chromaticity is not obtained. Also,
As a result of pattern formation experiments, the aspect ratio of the pattern was approximately 70 degrees, and a sufficient pattern shape was not obtained. Furthermore, when using a resist material containing a photosensitive compound having a film base of this resist material, the sensitivity for boat fishing is 100 to 3.
KrF excimer laser light (248,4
It is difficult to put it into practical use using nanometers (nm). In addition, in recent years, a chemically amplified resist material using acid generated during exposure as a medium has been proposed as a means of reducing the amount of exposure energy [H9Ito et al., Polym, Eng, Sci.
, vol. 23, p. 101.2 (1983). Various reports have been made regarding this. (For example, W, R, B
Runsvold et al., 5PIE'51989 Symp.
o,, 1086-40; T, Neenan et al., 5P
IF's 1989 Sympo, 1086-01)
. However, the resins used in these chemically amplified resist materials have a relatively large number of aromatic rings, and therefore have insufficient light transmittance in the vicinity of 248.4 nm.
There are problems such as poor heat resistance of the resin.

Regarding photosensitive compounds, for example, onium salts such as triphenylsulfonium tetrafluoroborate have poor solution stability, and although they exhibit their original performance immediately after preparing resist materials, they cannot be used on semiconductor manufacturing lines. It is said that it is difficult to put it into practical use in
In the case of sulfonic acid ester of 2,6-cinitrobenzyl, stability as a compound is recognized, but 2nitro-6-nitrotubenzaldehyde, which is produced by exposure to light, is a commonly used developer (tetramethylammonium hydroxide aqueous solution). ), problems such as scum remaining in exposed areas 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.

Therefore, it is difficult to obtain a good pattern shape, and a large amount of exposure energy is required. In addition, for chemically amplified resist materials, 248.4 nm of resin
It cannot be used unless the light transmittance of the surrounding area is improved or the heat resistance of the resin is improved, and at the same time, for photosensitive compounds, it generates acid with a lower amount of exposure energy, has solution stability, and The property that the product is soluble in a developer is required.

[Purpose of the Invention] The present invention was made in view of the above-mentioned situation, and it provides a resin that has high transparency after exposure to i-line light, f&ultraviolet light, such as KrF excimer laser light, and has heat resistance. and 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. The purpose is to

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

"A heat-resistant resin composed 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 a heat-resistant resin that generates an acid when exposed to light. A photosensitive compound represented by I];
A resist material comprising a solvent capable of dissolving both.

During the ceremony, RI! 1. R5 and RJ are each independently a hydrogen atom, a halogen atom, a linear bibranched or cyclic alkyl group, a haloalkyl group, -0R3 (however, R8 is a linear or branched alkyl group, an alkyl substituted silyl group, tetrahydropyranyl group, tetrahydrofuranyl group, haloalkyl group, alkoxyalkyl group, linear or branched alkyloxycarbonyl group), nitro group, nitrile group, amide group, or -COO group ( However, R represents a linear or branched alkyl group), and R represents a linear or branched alkyl group.
Q and R3 are each independently a hydrogen atom, a halogen atom, a linear bibranched or cyclic alkyl group, a haloalkyl group,
-0R3 (However, R8 represents a linear or branched alkyl group.

), nitro group or nitrile group, xo represents a carbon atom, phenyl group or naphthyl group, and n represents an integer of 0 to 3. ]'' The resist material of the present invention utilizes chemical amplification in order to reduce the amount of exposure energy as much as possible. Specifically, the resist material of the present invention comprises a component having a functional group that undergoes a chemical change upon heating in an atmosphere of acid generated from an acid generator upon exposure and becomes alkali-soluble, and a component that imparts heat resistance to the resin. The point of using a heat-resistant resin (hereinafter abbreviated as "resin according to the present invention") consisting of a component that has a function of preventing the entire resin from softening when heated, and a novel photosensitive compound. This is a new resist material with the following characteristics. A component (hereinafter referred to as
[Abbreviated as component J having a specific functional group.] ) include monomers such as P-hydroxystyrene derivatives and P-hydroxy-α-methylstyrene derivatives having a protecting group that can be removed with acid. For example, P
-methoxystyrene, p-isopropoxystyrene, p
(e"L-butoxystyrene, P-methoxymethoxystyrene, P-isopropoxymethoxystyrene, P-tetrahydropyranyloxystyrene, P-tetrahydrofuranyloxystyrene, p-)limethylsilyloxystyrene, p-tert-butoxycarpho 'Nyloxystyrene, P-impropoxycarbonyloxystyrene, or P-hydroxy-α-methylstyrene derivatives having the same protective groups as P-hydroxystyrene derivatives, but are of course limited to these. In addition, as a component that imparts heat resistance to the resin, the use of this component can prevent the entire resin from softening even when heated to 100°C or higher, more preferably 140°C or higher. For example, P-hydroxystyrene, P-chlorostyrene, styrene, α
- methylstyrene, fumaronitrile, monoisopropyl maleate, mono-tert-butyl maleate, di-tert-butyl maleate, monocyclohexyl maleate, maleic anhydride, N-phenylmaleimide, N-substituted phenylmaleimide, N-methylmaleimide, N-
Monomers such as n-butylmaleimide are more common.

For example, the resin according to the present invention has the following general formula [■ or [m]
Hail to you.

[In the formula, R1 is a methyl group, an isopropyl group, a tert-
Butyl group, methoxymethyl group, isopropoxymethyl group, tetrahydropyranyl group, tetrahydrofuranyl group,
It represents a trimethylsilyl group, a tert-butoxycarbonyl group, or an isopropoxycarbonyl group, R2 represents a hydrogen atom, a halogen atom, or a methyl group, and R3 represents a hydrogen atom, a P-hydroxyphenyl group, a P-chlorophenyl group, a phenyl group, or a cyano group. group or -COOR7 (however, R
7 represents a branched or cyclic alkyl group having 3 to 10 carbon atoms, or a hydrogen atom.

), R4 and R6 each independently represent a hydrogen atom, a methyl group, or a halogen atom, and R5 represents a hydrogen atom, a cyano group, or -C00R8 (however, R8 has 3 to 10 carbon atoms).
represents a branched or cyclic alkyl group, or a hydrogen atom), and R9 is a hydrogen atom or -COORIo(
However, RIO represents a branched or cyclic alkyl group having 3 to 10 carbon atoms, or a hydrogen atom. ), and k and 1 each independently represent a natural number. [wherein, X is an oxygen atom or N- (CH represents a phenyl group, q represents 0 or a natural number), 1' and P each independently represent 0 or a natural number, L/, R', R2,'
R3, R', R5, R6, R9 and k are the same as above.

] The compounds represented by these formulas [II] or [nI] are representative of the resins according to the present invention, but 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-isopropoxystyrene and α-methylstyrene copolymers, ρ-
Tetrahydropyranyloxystyrene and p-hydroxystyrene copolymer, p-jert-butoxystyrene and P-hydroxystyrene copolymer, p-tert-butoxycarbonyloxystyrene and maleic acid monocyclohexyl ester copolymer, p-tert , -butoxycarbonyloxystyrene and α-methylstyrene copolymer, p-tert-butoxystyrene and fumaronitrile copolymer, P-methoxymethoxystyrene and p-chlorostyrene copolymer, p-methoxymethoxystyrene and monocyclohexyl maleate Copolymer of ester and maleic anhydride, copolymer of P-tetrahydrofuranyloxystyrene and N-methylmaleimide, copolymer of p-tert-butoxycarbonyloxystyrene and P-hydroxystyrene and maleic anhydride, p - copolymer of tetrahydropyranyloxystyrene with P-hydroxystyrene and fumaronitrile, copolymer of p(ert-butoxycarbonyloxystyrene with P-hydroxystyrene and N-butylmaleimide, bicotrahydropyranyloxy Examples include copolymers of styrene, P-hydroxystyrene, and N-phenylmaleimide, but are not limited thereto.

The resin according to the present invention comprises a component having the above-mentioned specific functional group (
It can be easily obtained by copolymerizing one or more monomers and one or more components (monomers) that impart heat resistance to the resin according to a conventional method for producing copolymers. That is, 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 with radicals in an organic solvent such as benzene or toluene. 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]. Bottom, 50-100℃ in nitrogen stream
The polymerization reaction may be carried out for 1 to 10 hours, and after the reaction, the polymer compound may be isolated by post-treatment 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 (weight) of the resin according to the present invention is usually 1. ．．
000 to about 40,000, preferably 3,000 to
It is about 20,000.

In the photosensitive compound represented by the general formula [1] used in the present invention, the halogen atom and haloalkyl group represented by RL R1:ly Ra include chlorine, bromine, fluorine, and iodine; An alkyl group of a chain seven-branched or cyclic alkyl group, an alkyl group of a haloalkyl group, an alkyl group of a linear or branched alkyl group represented by R8, an alkyl-substituted silyl group represented by the same <R8 an alkyl group, an alkyl group of the same haloalkyl group, an alkyl group of the same alkoxyalkyl group, an alkyl group of the same alkoxy group, an alkyl group of the same straight-chain or branched alkyloxycarbonyl group, and a straight-chain or branched alkyl group represented by R6. Examples of the alkyl group of the branched alkyl group include alkyl groups having 1 to 10 carbon atoms such as methyl group, ethyl group, propyl group, butyl group, amyl group, hexyl group, octyl group, and decyl group. Also, master.

The halogen atom and haloalkyl group represented by R3 include chlorine, bromine, fluorine, and iodine, and the alkyl group of a linear bibranched or cyclic alkyl group, the alkyl group of a haloalkyl group, and the alkyl group of RQ Examples of straight-chain or branched alkyl groups include alkyl groups having 1 to 10 carbon atoms, such as methyl group, ethyl group, propyl group, butyl group, amyl group, hexyl group, octyl group, and decyl group. Can be mentioned.

Among the photosensitive compounds represented by the general formula [1] used in the present invention, particularly preferred ones are those represented by the following general formula [I a
] Compounds shown in the following are exemplified.

(In the formula, R♂~simple, X. and n are the same as above.) That is,
The present inventors are in the process of researching photosensitive compounds that generate acid upon exposure to light. When a group is introduced, the sulfonyl group is excited by the effect of the nitro group upon exposure, making it easier to dissociate the sulfonic acid ester, and nitrobenzenesulfonic acid can be efficiently generated at a low exposure amount due to the influence of the water present in the resist film. Heading 1 The present invention has been completed.

Typical compounds represented by the general formula [1a] include the following general formulas [1bj, [lc] and [I
Compounds shown in d can be mentioned.

(In the formula, R5-simple and n are the same as above.) The solvent used in the present invention may be any solvent as long as it can dissolve both the resin and the photosensitive compound, but usually 365N
Those having no absorption in the vicinity of m and 248.4 nm are more preferably used. More specific examples include ethyl cellosolve acetate, methyl cellosolve acetate, diethylene glycol dimethyl ether, ethyl lactate, methyl lactate, dioxane, and ethylene glycol monoisopropyl ether, but are not limited thereto.

The resin according to the present invention does not absorb light in a wavelength range of 300 nm or more, and has extremely high light transmittance for 5-ray light of 365 nm. Furthermore, it has been confirmed that acid generators generate acids even with i-line light, so chemical amplification can be utilized. Therefore, the resist material of the present invention utilizes a chemical amplification method to produce a low exposure amount of KrF excimer laser light (2
To explain the effect of the present invention on the effect of C, which is a resist material that can be patterned using KrF excimer laser light, i-line light, etc., using KrF excimer laser light, i-line light, etc. the below described(
Acid is generated according to the photoreaction shown in A).

When heat treatment is performed subsequent to the exposure step, the functional groups of the resin undergo a chemical change by the acid according to the reaction formula (B) below, and become alkali-soluble, which is eluted 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 in this way, a large difference in solubility in an alkaline developer occurs between the 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 CB), 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.

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

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 was poured into methanol to cause crystallization, and the precipitated product was collected by filtration and dried to obtain 120 g of p-tert-butoxystyrene-fumaronitrile copolymer (Lock catch: 10,000).

Example 1゜ Regis consisting of the following composition P-ere-butoxystyrene fumaronitrile copolymer (Compound obtained in Reference Example 1) A sheet material was prepared.

Diethylene glycol dimethyl ether 15.0g 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 190 seconds, a resist material film with a thickness of 1.0 μm was obtained (FIG. 1(a)). Next, KrF excimer laser light 3 of 248.4 nm was selectively exposed through a mask 4 (FIG. 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 (Fig. 1(C)).

FIG. 2 shows the ultraviolet ray spectral curves of this resist material film (1 μm) before and after exposure. The transmittance before and after exposure hardly changes, and even after exposure it shows a high transmittance of about 65%. Further, the positive pattern at this time had a well-shaped 0.3 μm line-and-space pattern with an aspect ratio of about 87 degrees. Further, the γ characteristics of this resist material film (1 μm) are shown in FIG. This material has a minimum exposure dose of 10mJ/at+
It had a high sensitivity of 2.

Example 2 A resist material was prepared in the same manner as in Example 1 except that the resin in Example 1 was changed to the styrene resin shown below, and the same experiment as in Example 1 was conducted.

p-tert-butoxystyrene-P-hydroxystyrene copolymer (approx. 13,000)
As a result, good results similar to those of Example 1 were obtained. The positive pattern obtained using this resist material is approximately 15 m long.
Pattern formation was possible with an exposure energy amount of J/cm2.

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 12 m long.
Pattern formation was possible with an exposure energy amount of J/cm2.

Example 4 A resist material was prepared in the same manner as in Example 2 except that the photosensitive compound in Example 2 was changed to the compound shown below, and the same experiment as in Example 2 was conducted.

As a result, good results similar to those in Example 2 were obtained. The positive pattern obtained using this resist material is approximately 12 m long.
Pattern formation was possible with an exposure energy amount of J/cm''.

Example 5 P-methoxymethoxystyrene maleic acid copolymer (Mw approximately 15,000) (k/1/p=2/1/1) 6.0 g Diethylene glycol dimethyl ether 15.0 g Prepared with the above composition An experiment similar to Example 1 was conducted using a resist material.

As a result, good results similar to those in Example 1 were obtained. The positive pattern obtained using this resist material is approximately 18 m long.
Pattern formation was possible with an exposure energy amount of J/an2.

[Effect of the invention] The resist neo material according to the present invention can be used with a light source of 400 nm or less, such as 365 nm i-line light, or deep ultraviolet light of 300 nm or less (
Deep UV), for example, KrF excimer laser light (24
When used as a resist material for exposure such as 84 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.

The five resist materials are particularly effective with i-line light, far ultraviolet light, and KrF excimer laser light, but 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. Further, FIG. 4 is a process cross-sectional view of a pattern forming method using a conventional resist material, and FIG. 5 is an ultraviolet ray spectral curve diagram of the conventional resist material (where the solid line is before exposure and the broken line is after exposure). FIG. 6 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 (1)

[Scope of Claims] (1) A heat-resistant resin composed 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; A resist material comprising a photosensitive compound represented by the following general formula [I] that generates an acid, and a solvent capable of dissolving both. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R_0^1, R_0^2, and R_0^3 each independently represent a hydrogen atom, a halogen atom, a linear, branched, or cyclic alkyl group, or a haloalkyl group. group, -OR_0^6 (However, R_0^6 is a linear or branched alkyl group, an alkyl-substituted silyl group, a tetrahydropyranyl group, a tetrahydrofuranyl group, a haloalkyl group, an alkoxyalkyl group, a linear or branched represents a branched alkyloxycarbonyl group), nitro group, nitrile group, amide group or -C
OOR_0^7 group (however, R_0^7 represents a linear or branched alkyl group), R_0^4, R
_0^5 each independently represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a haloalkyl group,
-OR_0^8 (However, R_0^8 represents a linear or branched alkyl group. ]) represents a nitro group or a nitrile group, X_0 represents a carbon atom, a phenyl group or a naphthyl group, and n represents a 0-3
represents an integer. (2) The resist material according to claim (1), wherein the photosensitive compound represented by the general formula [I] is a photosensitive compound represented by the following general formula [Ia]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I a] (In the formula, R_0^1 to R_0^5, X_0 and n are the same as above.) (3) Photosensitive compound represented by the general formula [I a] The resist material according to claim 2, wherein is a photosensitive compound represented by the following general formula [Ib]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [ I b] (In the formula, R_0^1 to R_0^5 are the same as above.) (4)
Claim (1) wherein the photosensitive compound represented by the general formula [I a] is a photosensitive compound represented by the following general formula [I c]
2) The resist material described in 2). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] (In the formula, R_0^1 to R_0^5 are the same as above.) (5
) The resist material according to claim (2), wherein the photosensitive compound represented by the general formula [Ia] is a photosensitive compound represented by the following general formula [Id]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I d] (In the formula, R_1^0 to R_0^5 and n are the same as above.) (6) It undergoes a chemical change by heating in an acid atmosphere and becomes alkali-soluble. A heat-resistant resin composed of a component having a functional group 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 are 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 or -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 1) represents a branched or cyclic alkyl group or a hydrogen atom. ), 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.)
where k and k each independently represent a natural number. ]
The resist material according to any one of claims (1) to (5), which is a resin represented by: (7) 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. ), 1' 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 branched or cyclic alkyl group or hydrogen atom as described above. ] The resist material according to any one of claims (1) to (5), which is a resin represented by the following.