JPH0882925A - Photosensitive material - Google Patents

Abstract

PURPOSE: To obtain a photosensitive material excellent in transparency to a single-wavelength light source and having satisfactory dry etching resistance. CONSTITUTION: This photosensitive material contains a compd. having a terpenoid skeleton preferably contg. a compd. having a monovalent menthyl or menthyl deriv. group represented by the formula, wherein R is H or monovalent hydrocarbon, R<1> is H, halogen, hydrocarbon, hydroxyl, alkoxyl, amino, imido, amido, sulfonyl, carboxyl, carbonyl or sulfonamido and R<1> 's may be different from each other and may bond to each other to form a ring.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photosensitive material suitable as a resist used for microfabrication in the manufacturing process of semiconductor devices and the like, and more particularly to ultraviolet light, deep UV
Light, 248 nm KrF excimer laser light, 193 nm
In particular, the present invention relates to a photosensitive material that is suitable when using short-wavelength light such as ArF excimer laser light, electron beam, or X-ray as an exposure energy source.

[0002]

2. Description of the Related Art In the manufacturing process of electronic parts such as semiconductor elements, a fine pattern is formed by using a photolithography technique. This technique is performed along the following steps. That is, first, the resist composition is applied onto a substrate or the like to form a thin film which will be a photoresist film. Next, after exposing this photoresist film, processing such as development and rinsing is performed to form a resist pattern. Then, by using the resist pattern as an etching resistant mask, the exposed surface of the substrate or the like is etched to open lines and windows having a minute width to form a desired pattern. Finally, the resist is dissolved and removed to obtain a thin film pattern.

In recent years, with the high integration of semiconductor elements,
In the photolithography technique, a processing technique capable of forming a finer pattern is required. In response to this demand, attempts have been made to shorten the wavelength of the exposure light source. For example, ArF excimer laser (wavelength 193 nm)
A process for forming a fine resist pattern has been developed which employs a fifth harmonic (wavelength 218 nm) of a YAG laser as a light source. As a result, the minimum line width of the wiring pattern extends to the submicron order. And
There is a tendency for further miniaturization.

Further, in the above process, it is required to form a resist pattern by using a resist having excellent dry etching resistance for the purpose of more effectively performing fine processing.

In this regard, it is known to use a photosensitive composition containing an aromatic compound as a resist material. As such a resist material, many materials containing a phenolic resin as a base material have been developed, but when these materials having short wavelength light as described above are used as an exposure light source, the absorption thereof is large, and at the time of exposure, The exposure light cannot sufficiently reach the part far from the surface of the resist film. As a result, there has been a problem that it is difficult to obtain a fine pattern with the conventional resist material.

On the other hand, it has been studied to use polymethylmethacrylate (PMMA) having no aromatic ring as a resin which absorbs less light, but these materials do not have sufficient dry etching resistance. There was a point.

[0007]

As described above, a photosensitive composition for realizing a submicron fine pattern is required to have a small light absorption and a sufficient dry etching resistance. There is.

Therefore, the present invention is directed to a short wavelength light source, particularly Kr.
An object of the present invention is to provide a photosensitive material having excellent transparency to F excimer laser light and ArF excimer laser light and having sufficient dry etching resistance.

[0009]

In order to solve the above-mentioned problems, the present invention provides a photosensitive material containing a compound having a terpenoid skeleton.

Specific examples of the photosensitive material include a resin whose main chain can be broken by exposure, a resin composition containing a compound whose solubility is improved by exposure (positive resist), a resin which can be crosslinked by exposure, Examples thereof include a resin composition (negative resist) containing a compound whose solubility is reduced by exposure.

Further, a chemically amplified resist which amplifies a photochemical reaction by a thermal reaction after exposure is effective.

As the positive type chemically amplified resist, a compound called a photoacid generator capable of generating an acid upon exposure and a compound having at least one bond capable of being decomposed by an acid, for example, a dissolution inhibiting group are used. And a photosensitive composition containing an alkali-soluble resin, if necessary.

The negative chemically amplified resist is a photosensitive composition containing a photoacid generator, an alkali-soluble resin, and a compound capable of crosslinking the resin component with an acid, or a compound having a solubility reduced by an acid. Is mentioned.

The photosensitive material of the present invention comprises a skeleton of a compound constituting such a photosensitive material, such as a main chain or a side chain of a resin component, a photosensitizer component, a photoacid generator or a dissolution inhibitor. It has a group having a terpenoid skeleton in the skeleton of the component.

The amount of the terpenoid skeleton in the solid content of the photosensitive material is preferably 5% by weight or more and 95% by weight or less. The reason for this is that when the amount of the terpenoid skeleton is less than 5% by weight, the dry etching resistance of the obtained pattern is lowered, and conversely, when it exceeds 95% by weight, resolution and sensitivity may be lowered. . A more preferable amount of the terpenoid skeleton is 20 to 75% by weight.

In the present invention, the compound having a terpenoid skeleton substantially conforms to the isoprene rule and has a C ₅ H ₈
A hydrocarbon having a basic composition of, and an oxygen-containing compound derived from the hydrocarbon, and a compound having a different degree of unsaturation, or a derivative of the compound, which can be used as a component of the photosensitive material described above. is there.

Specific examples of the hydrocarbon, the oxygen-containing compound derived therefrom, and the compound having a different degree of unsaturation include myrcene, carene, ocimene, pinene, limonene, camphene, terpinolene, tricyclene, terpinene, Fentchen, Ferrandrene, Silvestrene, Sabinene, Citronellol, Pinocampeol, Geraniol, Fentyl alcohol, Nellore, Borneol, Linalool, Menthol, Terpineol, Carveol, Twill alcohol, Citronellal, Yonone, Iron, Cinerol, Citral, Mentone , Pinol, cyclocitral, carbomentone,
Ascaridol, safranal, carbotanaceton, ferrandral, pimeritenone, citronellic acid, perillaldehyde, tsuyon, caron, dageton, camphor, bisabolen, santalen, zingiberen, cariophyllene, curcumen, sedren, kazinen, longifolene, sesquibenichen, farnesole, farnesole, farnesole Dole, carotol, casino, lanseol, oidesmol, cedrol, guayol, quessoglycol, cyperone, hinokylic acid, elemophyllone, santalic acid, zernbon, camphorene, podocarprene, millen, phyllocladen, totarene, phytol, sclareol, manol, hinokiol, Ferginol, Totarol, Sugiol, Ketomanoyl oxide, Manoyl oxide Abietic acid, pimaric acid, neoabietic acid, levopimaric acid, iso -d- pimaric acid,
Examples thereof include compounds having a skeleton such as agartenedicarboxylic acid, rubenic acid, triterpene, and carotenoid in the structure.

Among these compounds, compounds having a monocyclic terpenoid skeleton, or hemiterpenes, monoterpenes, diterpenes and sesquiterpenes are particularly advantageous in view of alkali solubility.

In the present invention, these compounds are used after being modified into components of the photosensitive material.

When a compound having a terpenoid skeleton is used as a resin component in a photosensitive material, a polymer having a menthyl group or a menthyl derivative group is preferable. Menthol (C ₁₀ H ₂₀ O), which is a raw material for a polymer having a menthyl group or a menthyl derivative group, is easily available, safe, inexpensive, and chemically very stable.

Hereinafter, the compound having a terpenoid skeleton in the photosensitive material of the present invention will be described in detail by taking a menthyl group or a menthyl derivative group as an example.

The menthyl group or the menthyl derivative group is represented by the general formula (1) shown below.

[0023]

[Chemical 6] (In the general formula (1), R is a hydrogen atom or a monovalent hydrocarbon group. R ¹ may be the same or different from each other, and a hydrogen atom, a halogen atom, a hydrocarbon group,
A hydroxyl group, an alkoxyl group, an amino group, an imide group, an amide group, a sulfonyl group, a carboxyl group, a carbonyl group, and a sulfonamide group, and R ^{1 s} may be bonded to each other to form a ring. ) In addition, in the above formula (1), the hydrocarbon group may be either an aliphatic group or an aromatic group, and may be further substituted with a hetero atom such as a nitrogen atom, an oxygen atom, a sulfur atom or phosphorus. Not limited. The aliphatic group may be saturated or may contain an unsaturated bond, and may be linear or branched. Further, the aliphatic group may include a cyclic compound. The aromatic group may be unsubstituted or may be substituted with the aliphatic group.

When R ¹ is an amino group, its hydrogen atom may be substituted with the above-mentioned hydrocarbon group.

Examples of the menthyl group or the menthyl derivative group represented by the general formula (1) include 8-butylmenthyl group, 8-β-naphthylmenthyl group, 8-α-naphthylmenthyl group and the like. The menthyl group and its derivative may be present in any part of the polymer and is not particularly limited. In order to obtain a polymer having this group, more generally, the above-mentioned group is introduced as a side chain of a compound having a polymerizable double bond to obtain a compound having a menthyl group or a menthyl derivative group, and then a monomer The desired polymer can be obtained by polymerization or copolymerization.

The amount of the menthyl group or the menthyl derivative group in the solid content of the photosensitive material is preferably at least 5% by weight and not more than 95% by weight. The reason for this is
This is because if the amount of the compound is less than 5% by weight, the dry etching resistance of the obtained pattern decreases, and conversely if it exceeds 95% by weight, the resolution and sensitivity may decrease. A more preferable amount of the menthyl group or the menthyl derivative group is 20 to 75% by weight.

In the present invention, the menthyl group or the menthyl derivative group can be present in any component of the photosensitive material. Therefore, even if these groups are present in any of the components, the amount thereof is preferably in the range described above in the solid content of the photosensitive material.

Further, the compound having a menthol group or a menthol derivative group in its skeleton is more preferably copolymerized with a vinyl compound and used as a resin component of the photosensitive material. In this case, higher resolution of the photosensitive material can be achieved.

Examples of vinyl compounds include methyl acrylate, methyl methacrylate, α-chloroacrylate, cyanoacrylate, trifluoromethyl acrylate, α-methylstyrene, trimethylsilyl methacrylate, trimethylsilyl α-chloroacrylate, trimethylsilylmethyl α-chloroacrylate. ，
Maleic anhydride, tetrahydropyranyl methacrylate, tetrahydropyranyl α-chloroacrylate, t-
Butyl methacrylate, t-butyl α-chloroacrylate, butadiene, glycidyl methacrylate, isobornyl methacrylate, menthyl methacrylate, norbornyl methacrylate, adamantyl methacrylate,
And allyl methacrylate and the like.

In particular, the copolymer composition is methyl methacrylate, α-chloromethacrylate, trifluoroethyl α.
In the case of an acrylic compound such as -chloro acrylate, trifluoromethyl acrylate or olefin sulfonic acid, it can be preferably used as a positive resist. When the acrylic compound having a vinyl group, an allyl group, or an epoxy group in the alcohol portion of the ester and the acrylic compound having 4 or more carbon atoms in the alcohol portion of the ester have a copolymer composition, a negative resist is used. Can be preferably used as. The acrylic compound is represented by the general formula (5) shown below.

[0031]

[Chemical 7] (In the general formula (5), R ⁷ represents a hydrogen atom or a monovalent organic group, and R ⁸ , R ⁹ and R ¹⁰ represent a hydrogen atom, a halogen atom or an alkyl group. R ⁸ , R ⁹ , And R ¹⁰ may be the same or different.) A compound containing a menthyl group or a menthyl derivative group, which is used for obtaining a polymer, is represented by the above-mentioned general formula (5). An acrylic compound is preferable because it can be easily polymerized or copolymerized.
The acrylic compound has the general formula (2)
It is represented by. The desired polymer can be obtained by homopolymerizing or copolymerizing this compound.

[0032]

Embedded image (In the general formula (2), R ³ is an organic group containing a menthyl group or a menthyl derivative group represented by the general formula (1), and R ⁴ is an alkyl group, a carboxyl group, an alkoxycarbonyl group, a halogen atom or It is a hydrogen atom.) Further, the above-mentioned menthyl group or menthyl derivative group may be introduced into a polyvalent carboxylic acid having a polymerizable structure as represented by the general formula (3) shown in Chemical formula 9 below. As a result, high resolution is achieved, which is preferable.

[0033]

[Chemical 9] (In the general formula (3), R ⁵ and R ⁶ are monovalent organic groups or hydrogen atoms, and at least one of them contains a menthyl group or a menthyl derivative group represented by the general formula (1). In the above general formula (3), one of R ⁵ and R ⁶ may be appropriately introduced with a group capable of being decomposed or crosslinked by an acid.

The compound represented by the general formula (3) is Z
The structure is not limited to the body or E-body, and
A polymer obtained by homopolymerizing or copolymerizing this monomer is used.

The compound represented by the above general formula (2) or (3) may be copolymerized with a compound which decomposes or crosslinks with an acid. The compound that decomposes or crosslinks with this acid is represented by the following general formula (4).

[0036]

[Chemical 10] (In the above general formula (4), R ¹³ is a monovalent organic group,
¹⁴ is an alkyl group, a halogen atom or a hydrogen atom. ) When the compound represented by the general formula (4) is a compound that decomposes with an acid, in the general formula (4),-(C =
O) O-R ¹³ may be a group that is decomposed by an acid described below, or R ¹³ may be an organic group containing a group that is decomposed by such an acid.

In the present invention, when the monomer and copolymer having a menthyl group or a menthyl derivative group are decomposed by the action of an acid to be soluble in a developing solution, the photosensitive material of the present invention is It can be used as a positive chemically amplified resist, while when it becomes insoluble in a developer due to the action of acid, the photosensitive composition of the present invention should be used as a negative chemically amplified resist. Is possible.

The positive type chemically amplified resist is
An acid is generated by irradiating with (a) an alkali-soluble resin that is a resin component, (b) a dissolution inhibitor that is a compound that decomposes with an acid, and (c) light such as actinic radiation, energy radiation, or substance radiation. It is a photosensitive material containing three components of a photoacid generator which is a compound. The alkali-soluble resin can also act as a dissolution inhibitor at the same time by having an acid-decomposable group, that is, a dissolution inhibiting group as its copolymer composition. The positive type chemically amplified resist is insoluble in an alkaline solution in an unexposed state (unirradiated with actinic radiation) due to the presence of a dissolution inhibitor. Therefore, by exposing the chemically amplified resist layer applied to the substrate to light and treating it by baking, acid is generated from the photoacid generator. This acid decomposes the aforementioned dissolution inhibitor and becomes soluble in the alkaline solution. Such a resist structure is a positive type, but in the case of a negative type chemically amplified resist,
Instead of the component (b), a compound which can crosslink the resin component with an acid or a compound whose solubility is reduced by an acid is contained.

The chemically amplified resist can be used as an arbitrary positive or negative resist depending on the components contained therein. For example, when used as a positive type, the resin may be a vinyl-based compound having the structure represented by the general formula (1) in its side chain, or an acrylic compound represented by the general formula (5), and an acid compound. A copolymer with a monomer having a group capable of decomposing by is preferred.

In particular, the resin component is the above general formula (2).
Copolymerization of a monomer represented by or a monomer represented by the general formula (3) with, for example, a compound containing a functional group capable of being decomposed or cross-linked by an acid represented by the general formula (4). In the case of being a combination, it can be suitably used as a chemically amplified resist by containing a photo-acid generator.

However, in the compound represented by the general formula (3), at least one of R ⁵ and R ⁶ is an organic group containing a menthyl group or a menthyl derivative group, and the other is an organic group capable of being decomposed or crosslinked with an acid. In such a case, by adding a photo-acid generator to the homopolymer, it becomes possible to suitably use it as a chemically amplified resist.

Examples of the group decomposable by an acid include isopropyl ester, ethyl ester, methyl ester, methoxymethyl ester, ethoxyethyl ester, methylthiomethyl ester, tetrahydropyranyl ester, tetrahydrofuranyl ester, methoxyethoxymethyl ester and 2-trimethylsilyl. Ethoxymethyl ester, 2,2,2-trichloroethyl ester, 2
-Chloroethyl ester, 2-bromoethyl ester,
2-iodoethyl ester, 2-fluoroethyl ester, ω-chloroalkyl ester, 2-trimethylsilylethyl ester, 2-methylthioethyl ester,
1,3-dithianyl-2-methyl ester, t-butyl ester, cyclopentyl ester, cyclohexyl ester, 3-oxocyclohexyl ester, allyl ester, 3-buten-1-yl ester, isobornyl ester, 4-trimethylsilyl-2 -Buten-1-yl ester, 9-anthrylmethyl ester, 2-
9 ', 10'-dioxo-anthryl methyl ester,
1-pyrenyl methyl ester, 2-trifluoromethyl-6-chromyl methyl ester, piperonyl ester,
4-picolyl ester, trimethylsilyl ester, triethylsilyl ester, isopropyldimethylsilyl ester, di-t-butylmethylsilyl ester, thiol ester, oxazole, 2-alkyl-1,3-
Oxazoline, 4-alkyl-5-oxo-1,3-oxazoline, 5-alkyl-4-oxo-1,3-dioxolane, orthoester, pentaaminecobalt complex, triethylstannyl ester, tri-n-
Butylstannyl ester, N, N-dimethylamide, pyrrolidine amide, piperidine amide, 5,6-dihydrophenanthridine amide, N-7-nitroindolyl ester, N-8-nitro-1,2,3,4- Tetrahydroquinolylamide, hydrazide, N-phenylhydrazide, and
Esters such as N, N'-diisopropylhydrazide; t
-Butoxycarbonyl ether, methyl ether, methoxymethyl ether, methylthiomethyl ether, t-
Butylthiomethyl ether, t-butoxymethyl ether, 4-pentenyloxymethyl ether, t-butyldimethylsiloxymethyl ether, sexyldimethylsiloxymethyl ether, 2-methoxyethoxymethyl ether, 2,2,2-trichloroethoxymethyl Ether, bis
-2'-chloroethoxy-methyl ether, 2'-trimethylsilylethoxymethyl ether, 2'-triethylsilylethoxymethyl ether, 2'-triisopropylsilylethoxymethyl ether, 2'-t-butyldimethylsilylethoxymethyl ether, tetrahydro Pyranyl ether, tetrahydrothiopyranyl ether, 3-bromotetrahydropyranyl ether, 1-methoxycyclohexyl ether, 4-methoxytetrahydropyranyl ether, 4-methoxytetrahydrothiopyranyl ether, 4-methoxytetrahydrothiopyranyl ether-
S, S-dioxide, 1,4-dioxan-2-yl ether,
Tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 2,3,3a, 4,5,6,7,7a-octahydro-7,8,8
-Trimethyl-4,7-methanobenzofuran-2-yl ether, 1-ethoxyethyl ether, 1-2'-chloroethoxy-ethyl ether, 1-methyl-1-methoxyethyl ether, 2,2,2-trichloroethyl Ether, 2-trimethylsilylethyl ether, t-butyl ether, allyl ether, 4,4 ', 4 "-tris-4', 5'-dichlorophthalimidophenyl-methyl ether, 4,4 ', 4"-tris-4' ,
5'-dibromophthalimidophenyl-methyl ether, 4,
4 ', 4 "-Tris-4', 5'-iodophthalimidophenyl-methyl ether, 9-anthryl ether, 9-9'-phenyl-
10'-oxo-anthryl ether (tritylone ether), 1,3-benzodithiolan-2-yl ether, benzisothiazolyl-S, S-dioxide ether, trimethylsilyl ether, triethylsilyl ether, triisopropylsilyl ether Ethers such as dimethyl isopropyl silyl ether, diethyl isopropyl silyl ether, dimethyl sexyl silyl ether, and t-butyl dimethyl silyl ether; methylene acetal, ethylidene acetal, 2,2,2-trichloroethylidene acetal, 2,2, Acetals such as 2-tribromoethylidene acetal and 2,2,2-triiodoethylidene acetal; 1-t-butylethylidene ketal, isopropylidene ketal (acetonide), cyclopentylidene ketal, cyclohexyl Denketaru,
And ketals such as cycloheptylidene ketal; methoxymethylene acetal, ethoxymethylene acetal, dimethoxymethylene orthoester, 1-methoxyethylidene orthoester, 1-ethoxyethylidene orthoester, 1,2-dimethoxyethylidene orthoester, 1- Cyclic orthoesters such as N, N-dimethylaminoethylidene orthoester and 2-oxacyclopentylidene orthoester; trimethylsilyl ketene acetal, triethylsilyl ketene acetal, triisopropylsilyl ketene acetal, and t-butyldimethyl Silyl ketene acetals such as silyl ketene acetals; di-t-butyl silyl ether, 1,3-1 ', 1', 3 ', 3'-tetraisopropyldisiloxanilidene ether, and Silyl ethers such as tetra -t- butoxy-1,3-diisopropyl isopropylidene ether; dimethyl acetal, dimethyl ketal,
Bis-2,2,2-trichloroethyl acetal, bis-2,2,2-
Tribromoethyl acetal, bis-2,2,2-triiodoethyl acetal, bis-2,2,2-trichloroethyl ketal, bis-2,2,2-tribromoethyl ketal, bis-2,
Acyclic acetals or ketals such as 2,2-triiodoethyl ketal, diacetyl acetal, and diacetyl ketal; 1,3-dioxane, 5-methylene-
1,3-dioxane, 5,5-dibromo-1,3-dioxane, 1,3-
Dioxolane, 4-bromomethyl-1,3-dioxolane, 4-
Cyclic acetals or ketals such as 3'-butenyl-1,3-dioxolane and 4,5-dimethoxymethyl-1,3-dioxolane; S, S'-dimethylacetal,
S, S'-Dimethylketal, S, S'-Diethylacetal, S,
S'-diethyl ketal, S, S'-dipropyl acetal, S,
S'-dipropyl ketal, S, S'-dibutyl acetal, S,
S'-dibutyl ketal, S, S'-dipentyl acetal, S,
S'-dipentyl ketal, S, S'-diacetyl acetal,
And acyclic dithioacetals or ketals such as S, S'-diacetyl ketal; 1,3-dithianacetal, 1,3-dithianketal, 1,3-dithiolane acetal, and 1,3-dithiolane ketal Cyclic dithioacetals or ketals; O-trimethylsilyl-S-alkyl acetals; O-trimethylsilyl-S-alkyl ketals; acyclic monothioacetals such as O-methyl-S-2-methylthioethyl acetal; Acyclic monothioketals such as O-methyl-S-2-methylthioethyl ketal; cyclic monothioacetals or ketals such as 1,3-oxathiolane acetal, diselenoacetal, and diselenoketal; O- Trimethylsilyl cyanohydrin, O-1
-Cyanohydrins such as ethoxyethyl cyanohydrin and O-tetrahydropyranyl cyanohydrin; Hydrazones such as N, N-dimethylhydrazone; Oxime derivatives, oximes such as O-methyloxime; Oxazolidine, 1-methyl-2-1'- Examples thereof include hydroxyalkyl-imidazole and cyclic derivatives such as N, N-dimethylimidazolidine.

More preferably, t-butyl methacrylate, ethoxyethyl methacrylate, 3-oxocyclohexyl methacrylate, t-butyl-3-naphthyl-
And t-butyl esters such as 2-propenoate, isobornyl methacrylate, trimethylsilyl methacrylate, and tetrahydropyranyl methacrylate; trimethylsilyl ester; tetrahydropyranyl ester. In this case, acrylate may be used instead of methacrylate.

The content of the monomer having a menthyl group or a menthyl derivative group in the skeleton in such a copolymer is preferably in the range of 5 mol% to 95 mol% with respect to the total moles of all the monomers. If it is less than 5 mol%, the dry etching resistance of the obtained pattern is lowered, and if it exceeds 95 mol%,
It is not preferable because the resolution and sensitivity will be reduced. The more preferable content of the monomer is 20 to 75.
Mol%.

When a monomer having a dissolution inhibiting group is contained in the polymer as a copolymer composition, the content thereof is 10 mol% to 95% based on the total number of moles of the whole monomers.
A range of mol% is desirable. If it is less than 10 mol%, a sufficient dissolution inhibiting effect cannot be imparted, while if it exceeds 95 mol%, the resolution is lowered. The content of the monomer having a dissolution inhibiting group is more preferably 15 mol% to 70 mol%. Further, an alkali-soluble group may be further contained as a base resin component of the photosensitive material of the present invention. As the monomer containing an alkali-soluble group,
It is possible to use one that itself dissolves in an alkali or a base. For example, a monomer containing a carboxylic acid, a sulfonic acid, or an acid anhydride can be mentioned. Two or more alkali-soluble groups may be present in the monomer. These monomers include ester, alcohol, amine,
Other functional groups such as imines, imides, sulfonamides, amides may be present. Such a monomer may be mixed with the polymer thereof and the compound represented by the general formula (2) or the polymer including the compound represented by the general formula (3) as a monomer. However, it may be a copolymer composition.

As the compound having an alkali-soluble group, the compound represented by the above general formula (5) is preferable. In this compound, when R ⁷ is a monovalent organic group, it may have a group soluble in an alkali or a base.

Further, (a) an alkali-soluble resin, (b)
In a photosensitive material containing three components of a dissolution inhibitor and (c) a photoacid generator, when a menthyl or menthyl derivative group is present in the skeleton of an alkali-soluble resin, it is represented by the above general formula (2). And a compound represented by the general formula (3) and a compound having an alkali-soluble group represented by the general formula (5) are preferably used. Further, in the compound represented by the general formula (3), at least one of R ⁵ and R ⁶ is an organic group containing a menthyl group or a menthyl derivative group, and the other is an organic group containing a hydrogen atom or an alkali-soluble group. If
The homopolymer can also be used as an alkali-soluble resin. Needless to say, at this time, a monomer having a dissolution inhibiting group may further have a copolymer composition.

Other copolymerizable components in the base resin of the photosensitive material of the present invention include acrylic acid ester monomers, imide monomers, sulfonamide monomers, amide monomers and acrylic alkylaminosulfonylalkyl esters represented by the general formula (5). May be further contained. For example, a methacrylic acid ester monomer, an acrylic acid ester monomer, a crotonic acid ester monomer, a tiglylic acid ester monomer, etc. can be mentioned.

In this case, it is possible to appropriately adjust the alkali solubility of the resin component by introducing an arbitrary organic group into R ⁷ of the general formula (5).

When the copolymer composition contains an alkali-soluble group, the content of the monomer having the alkali-soluble group is preferably in the range of 1 mol% to 95 mol% with respect to the total number of moles of the monomers. If it is less than 1 mol%, the alkali solubility after exposure may be insufficient, while 95
If it exceeds mol%, the sensitivity may decrease. In addition,
The content of the alkali-soluble group is more preferably 1 to 70.
Mol%.

Further, when the acrylic acid ester monomer represented by the general formula (5) is contained, it is preferable to add 1 to 80% of this monomer to the total number of the monomers. If it deviates from this range, the resolution will decrease. The content of the acrylic acid ester monomer further contained is more preferably 1 to 70%. Further, several kinds of copolymers can be mixed and used as the base resin. Further, not only the copolymers but also the compounds represented by the above general formulas (2) to (5) can be used as a base resin by appropriately mixing those homopolymers.

The photo-acid generator contained as a component of the chemically amplified resist composition is a compound which generates an acid upon irradiation with actinic radiation, such as an aryl onium salt,
Examples thereof include naphthoquinone diazide compound, diazonium salt, sulfonate compound, sulfonium compound, iodonium compound, and sulfonyl diazomethane compound.

As examples of these compounds, specifically,
Triphenylsulfonium triflate, diphenyliodonium triflate, 2,3,4,4-tetrahydroxybenzophenone-4-naphthoquinonediazide sulfonate, 4-N-phenylamino-2-methoxyphenyldiazonium sulphate, 4-N -Phenylamino-2-methoxyphenyldiazonium p-ethylphenylsulfate, 4-
N-phenylamino-2-methoxyphenyldiazonium 2-
Naphthyl sulfate, 4-N-phenylamino-2-methoxyphenyldiazonium phenylsulfate, 2,5-diethoxy-4-N-4'-methoxyphenylcarbonylphenyldiazonium 3-carboxy-4-hydroxyphenylsulfate, 2 -Methoxy-4-N-phenylphenyldiazonium 3-carboxy-4-hydroxyphenylsulfate, diphenylsulfonylmethane, diphenylsulfonyldiazomethane, diphenyldisulfone, α-methylbenzointosylate, pyrogallol trimesylate, and benzointosylate To be Further, the compounds shown in the following Tables 1 and 2 and Chemical formulas 11 to 14 may be used.

[0054]

[Table 1]

[0055]

[Table 2]

[0056]

[Chemical 11]

[0057]

[Chemical 12]

[0058]

[Chemical 13]

[0059]

Embedded image Further, the iodonium salt shown in Chemical formulas 15 and 16, the sulfonium salt shown in Chemical formulas 17 to 19, the disulfone derivative shown in Chemical formula 20, and the imidosulfone derivative shown in Chemical formula 21 can also be used.

[0060]

[Chemical 15]

[0061]

Embedded image

[0062]

[Chemical 17]

[0063]

[Chemical 18]

[0064]

[Chemical 19]

[0065]

Embedded image

[0066]

[Chemical 21] Further, compounds shown in Chemical formulas 22 to 25 below may be used.

[0067]

[Chemical formula 22]

[0068]

[Chemical formula 23]

[0069]

[Chemical formula 24]

[0070]

[Chemical 25] In the formula shown in Chemical formula 25, C ¹ and C ² form a single bond or a double bond, and R ′ is —CF ₃ , —CF ₂ CF ₃ ,
A group selected from the group consisting of —CF ₂ CF ₂ H and — (CF ₂ ) _n —Z ′ (where n is 1 to 4,
Z ′ is selected from H, alkyl, aryl, and groups shown in the chemical formula 26 below. ) Also, X ′ and Y ′ are
(1) forming a monocyclic or polycyclic ring which may contain one or more heteroatoms, (2) forming a fused aromatic ring, or (3) independently hydrogen, alkyl or aryl. Alternatively, (4) it may be attached to a residue containing another sulfonyloxyimide, or (5) it may be attached to a polymerizable chain or backbone.

[0071]

[Chemical formula 26] In particular, when a photoacid generator having a naphthalene skeleton is used,
It is preferable because the light transmittance around 193 nm is increased.

Examples of the photoacid generator having a naphthalene skeleton include naphthalene, pentalene, indene, azulene, heptalene, biphenylene, as-indacene, s-
Indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene,
Acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, naphthacene, pleiaden,
Picene, perylene, pentaphene, pentacene, tetraphenylene, hexaphene, hexacene, rubicene, coronene, trinaphthylene, heptaphene, heptacene,
Pyrantrene, obalene, dibenzophenanthrene, benz [a] anthracene, dibenzo [a, j] anthracene, indeno [1,2-a] indene, anthra [2,1-a] naphthacene,
Sulfonyl or sulfonate compounds having 1H-benzo [a] cyclopento [j] anthracene ring; naphthalene, pentalene, indene, azulene, heptalene,
Biphenylene, as-indacene, s-indacene, acenaphthylene, fluorene, phenalene, phenanthrene,
Anthracene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, naphthacene, pleiaden, picene, perylene,
Pentaphene, pentacene, tetraphenylene, hexaphene, hexacene, rubicene, coronene, trinaphthylene, heptaphene, heptacene, pyrantrene, ovarene, dibenzophenanthrene, benz [a] anthracene, dibenzo [a, j] anthracene, indeno [1,2-a] Indene, anthra [2,1-a] naphthacene, 1H-benzo [a] cyclopent [j] 4-quinonediazide compound having hydroxy compound in anthracene ring; naphthalene, pentalene,
Inden, azulene, heptalen, biphenylene, as-
Indacene, s-indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, naphthacene,
Pleiaden, picene, perylene, pentaphene, pentacene, tetraphenylene, hexaphene, hexacene, rubicene, coronene, trinaphthylene, heptaphene, heptacene, pyrantrene, ovalene, dibenzophenanthrene, benz [a] anthracene, dibenzo [a, j].
Anthracene, Indeno [1,2-a] Inden, Anthra [2,
Examples thereof include salts of 1-a] naphthacene and 1H-benzo [a] cyclopento [j] anthracene having a side chain with sulfonium or iodonium triflate. In particular, a salt with a sulfonyl or sulfonate compound having a naphthalene ring or an anthracene ring: a 4-quinonediazide compound having a hydroxy compound in naphthalene or anthracene: a salt of sulfonium or iodonium triflate having a naphthalene or anthracene rule chain is preferable. Among these compounds, trinaphthyl sulfonium triflate, dinaphthyl iodonium triflate, dinaphthyl sulfonyl methane, Midori Kagaku NAT-105 (CAS. No. [137867-6]).
1-9]), manufactured by Midori Kagaku, NAT-103 (CAS.N.
o. [131582-00-8]). NA manufactured by Midori Kagaku
I-105 (CAS. No. [85342-62-
7]) and TAZ-106 (CA manufactured by Midori Kagaku)
S. No. [69432-40-2]), Midori Kagaku NDS-105, Midori Kagaku CMS-105, Midori Kagaku DAM-301 (CAS. No. [138529].
-81-4]), Midori Kagaku SI-105 (CAS.
No. [34694-40-7]), ND manufactured by Midori Kagaku
I-105 (CAS. No. [133710-62-
0]), EPI-105 (CAS. No.
[135133-12-9]), PI-1 manufactured by Midori Kagaku
05 (CAS. No. [41580-58-9]) is preferable. Further, the compounds shown in Chemical formulas 27 to 31 below may be used.

[0073]

[Chemical 27]

[0074]

[Chemical 28]

[0075]

[Chemical 29]

[0076]

[Chemical 30]

[0077]

[Chemical 31] More preferred among these compounds are trinaphthyl sulfonium triflate, dinaphthyl iodonium triflate, dinaphthyl sulfonyl methane, NAT-105 (CAS. No. [1.
37867-61-9]), NDI-10 manufactured by Midori Kagaku
5 (CAS. No. [133710-62-0]). And NAI-105 (CAS. No.
[85342-62-7]).

Further, it is more preferable to use a compound having a terpenoid skeleton as the photo-acid generator because the light transmittance in the vicinity of 193 nm can be further increased.

As the compound having a terpenoid skeleton, those described above can be used. That is, for example, myrcene, karen, ocimene, pinene, limonene, camphene, terpinolene, tricyclene, terpinen, fenchen, ferrandrene, silvestrene, sabinene, citronellol, pinocampheol,
Geraniol, fentyl alcohol, nerol, borneol, linalool, menthol, terpineol,
Carveol, twill alcohol, citronellal, yonone, iron, cinerol, citral, menthone, pinol, cyclocitral, carbomentone, ascaridol, safranal, carbotanaceton, ferrandral, pimeritenone, citronellolic acid, perylaldehyde, thuyoung, caron, dagueton, shounou , Bisabolen, santalen, zingiberene, cariophyllene, curcumen, sedren, kazinen, longifolene, sesquibenhen, farnesol, patchouli alcohol, nerolidol, carrotol, casino, lanseol, eudesmol, sedrol, guayol, quessoglycol, cyperone, hinokironic acid, elequinoic acid, ， Santalic acid ， Serumbon ， Kanphorene ， Podocarprene ， Millen ， Philokradene Totalene, phytol, sclareol, manol, hinokiol, ferguinol, totalol, sugiol, ketomanoyl oxide, manoyl oxide, abietic acid, pimaric acid, neoabietic acid, levopimaric acid, iso-d-pimaric acid, agatenedicarboxylic acid, Sulfonyl or sulfonate compounds containing rubenic acid, triterpenes, or carotenoids; myrcene, carene, ocimene, pinene, limonene, camphene, terpinolene, tricyclene, terpinene, fenchen, ferrandrene, silvestrene, sabinene, citronellol, pinocampheol, Geraniol, fentyl alcohol, nerol, borneol,
Linalool, menthol, terpineol, carveol, twill alcohol, citronellal, yonone, iron, cinerol, citral, menthone, pinol, cyclocitral, carbomentone, ascaridol, safranal, carbotanaceton, ferrandral, pimeritenone, citronelloic acid, perylaldehyde, thuyoung. , Karon, Dageton, Camphor, Bisabolen, Santarem, Zingiberen, Cariophyllen, Curcumen,
Sedren, Kazinen, Longifolen, Sesqui Benichen,
Farnesol, patchouli alcohol, nerolidol,
Carotol, casino, lanseol, edesmol, cedrol, guayol, quessoglycol, cyperone, hinokic acid, eremophilon, santalic acid, zerumbone, camphorene, podocarprene, millen, phyllocladen, totarene, phytol, sclareol, manol, hinokiol, ferguinol, Totarol, Sugiol, Ketomanoyl oxide, Manoyl oxide,
4-quinonediazide compounds having hydroxy compounds in abietic acid, pimaric acid, neoabietic acid, levopimaric acid, iso-d-pimaric acid, agatenedicarboxylic acid, rubenic acid, triterpenes, or carotenoids; myrcene, carene, ocimene, pinene, Limonene, camphene, terpinolene, tricyclene, terpinen, fenchen, ferrandrene, silvestrene, sabinen,
Citronellol, Pinocampheol, Geraniol,
Fentyl alcohol, nerol, borneol, linalool, menthol, terpineol, carveol,
Twill alcohol, citronellal, yonon, iron,
Cinerol, citral, menthone, pinol, cyclocitral, carbomentone, ascaridol, safranal, carbotanaceton, ferrandral, pimeritenone, citronellolic acid, perillaldehyde, thuyoung,
Karon, Dageton, Camphor, Bisabolen, Santalen, Zingiberen, Cariophyllen, Curcumen, Sedren, Kazinen, Longifolen, Sesquibenien, Farnesol, Patchouli alcohol, Nerolidol, Carotol, Casino, Lanceol, Oidesmol,
Cedrol, Guayol, Kessoglycol, Cyperone, Hinokinoic acid, Eremophilon, Santalic acid, Zerumbon, Camphorene, Podocarprene, Millen, Phyllocladen, Totarene, Phytol, Sclareol, Manol, Hinokiol, Feruginol, Totarol, Sugiol, Ketomanoyloxide, Ma Examples thereof include salts of noyl oxide, abietic acid, pimaric acid, neoabietic acid, or sulfonium or iodonium triflate having a carotenoid side chain. In particular, trimentyl sulfonyl methane, trimentyl sulfonium triflate, dimenthyl methyl sulfonium triflate, menthyl dimethyl sulfonium triflate, dimenthyl iodonium triflate, and menthyl methyl iodonium triflate are preferable.

The photo-acid generator added is preferably in the range of 0.001 mol% to 50 mol% with respect to the entire base resin. If it is less than 0.001 mol%, a sufficient amount of acid is not generated, and pattern formation may be impossible,
On the other hand, when it exceeds 50 mol%, the resolution and sensitivity are deteriorated, which is not preferable. The content of the photo-acid generator is more preferably 0.01 with respect to the entire base resin.
It is mol% -40 mol%.

The photosensitive material of the present invention is a positive type chemically amplified resist containing three components: (a) alkali-soluble resin, (b) dissolution inhibitor, and (c) photoacid generator. Needless to say, even when a monomer having a dissolution inhibiting group is introduced as a copolymer composition of resin components, a dissolution inhibiting agent may be further contained.

This dissolution inhibitor has a substituent or a functional group capable of decomposing in the presence of an acid, like the aforementioned dissolution inhibiting group, and the product after decomposition is-(C = O) O-,-OS (= O) _2- , or-
There is no particular limitation as long as it produces O-.

For example, the phenolic compound is t-butoxycarbonyl ether, methyl ether, methoxymethyl ether, methylthiomethyl ether, t-butylthiomethyl ether, t-butoxymethyl ether, 4-pentenyloxymethyl ether, t-butyl. Dimethylsiloxymethyl ether, sexyldimethylsiloxymethyl ether, 2-methoxyethoxymethyl ether, 2,2,
2-trichloroethoxymethyl ether, bis-2'-chloroethoxy-methyl ether, 2'-trimethylsilylethoxymethyl ether, 2'-triethylsilylethoxymethyl ether, 2'-triisopropylsilylethoxymethyl ether, 2'-t- Butyldimethylsilylethoxymethyl ether, tetrahydropyranyl ether, tetrahydrothiopyranyl ether, 3-bromotetrahydropyranyl ether, 1-methoxycyclohexyl ether, 4-methoxytetrahydropyranyl ether, 4-methoxytetrahydrothiopyranyl ether, 4-methoxytetrahydrothiopyrani Ruether-S, S-dioxide, 1,4-dioxan-2-yl ether,
Tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 2,3,3a, 4,5,6,7,7a-octahydro-7,8,8
-Trimethyl-4,7-methanobenzofuran-2-yl ether, 1-ethoxyethyl ether, 1-2'-chloroethoxy-
Ethyl ether, 1-methyl-1-methoxyethyl ether, 2,2,2-trichloroethyl ether, 2-trimethylsilylethyl ether, t-butyl ether, allyl ether, 4,4 ', 4 "-tris-4', 5 '-Dichlorophthalimidophenyl-methyl ether, 4,4', 4 "-Tris-4 ', 5'-dibromophthalimidophenyl-methyl ether, 4,4', 4" -Tris-4 ', 5'-iodophthalimide Phenyl-methyl ether, 9-anthryl ether, 9-9'-phenyl-10'-oxo
-Anthryl ether (tritylone ether), 1,3-benzodithiolan-2-yl ether, benzisothiazolyl-S, S-dioxide ether, trimethylsilyl ether, triethylsilyl ether, triisopropylsilyl ether, dimethylisopropylsilyl Examples include ethers, diethyl isopropyl silyl ethers, dimethyl thexyl silyl ethers, and compounds converted to t-butyl dimethyl silyl ethers. In particular, a phenolic compound, preferably a naphthol compound
A compound protected with -butoxycarbonyl group, t-butoxycarbonylmethyl group, trimethylsilyl group, t-butyldimethylsilyl group, or tetrahydropyranyl group is most suitable. Alternatively, polycarboxylic acid isopropyl ester, ethyl ester, methyl ester, methoxymethyl ester, methylthiomethyl ester, tetrahydropyranyl ester, tetrahydrofuranyl ester, methoxyethoxymethyl ester, 2-trimethylsilylethoxymethyl ester, 2,2,2- Trichloroethyl ester, 2-chloroethyl ester, 2-bromoethyl ester, 2-iodoethyl ester, 2-fluoroethyl ester, ω-chloroalkyl ester, 2-
Trimethylsilylethyl ester, 2-methylthioethyl ester, 1,3-dithianyl-2-methyl ester, t-
Butyl ester, cyclopentyl ester, cyclohexyl ester, allyl ester, 3-buten-1-yl ester, 4-trimethylsilyl-2-buten-1-yl ester, 9-anthrylmethyl ester, 2-
9 ', 10'-dioxo-anthrylmethyl ester,
1-pyrenyl methyl ester, 2-trifluoromethyl-6-chromyl methyl ester, piperonyl ester,
4-picolyl ester, trimethylsilyl ester, triethylsilyl ester, t-butyldimethylsilyl ester, isopropyldimethylsilyl ester, di-t
-Butylmethylsilyl ester, thiol ester, oxazole, 2-alkyl-1,3-oxazoline, 4
-Alkyl-5-oxo-1,3-oxazoline, 5-
Alkyl-4-oxo-1,3-dioxolane, orthoester, pentaaminecobalt complex, triethylstannyl ester, tri-n-butylstannyl ester, N, N-dimethylamide, pyrrolidineamide, piperidineamide, 5,6-dihydro Phenanthridinamide,
N-7-nitroindolyl ester, N-8-nitro-1,2,
3,4-tetrahydroquinolylamide, hydrazide, N-phenylhydrazide, N, N'-diisopropylhydrazide,
Alternatively, t-butyl ester or the like may be used. Further, the compounds shown in the following chemical formulas 32 to 44 can also be used.

[0084]

[Chemical 32]

[0085]

[Chemical 33]

[0086]

Embedded image

[0087]

Embedded image

[0088]

Embedded image

[0089]

Embedded image

[0090]

[Chemical 38]

[0091]

[Chemical Formula 39]

[0092]

[Chemical 40]

[0093]

Embedded image

[0094]

Embedded image

[0095]

[Chemical 43]

[0096]

[Chemical 44] In particular, a compound obtained by protecting polyhydroxynaphthol having a naphthalene skeleton in its structure with a t-butoxycarbonyl group is preferable because it has a high transmittance at 193 nm.

Further, the compound represented by the general formula (6) shown in the following chemical formula 45 can also be used.

[0098]

[Chemical formula 45] (In the general formula (6), R ¹¹ and R ¹² are hydrogen atoms,
It represents a halogen atom, a cyano group, a nitro group, a silyl group, or a monovalent organic group, which may be the same or different. Also,
R ¹¹ and R ¹² may combine with each other to form a ring. X is> C = O or -SO ₂ - shows a. Y represents a divalent organic group. Any one of R ¹¹ , R ^{12 and} Y
One or more has a substituent or a functional group that is decomposed by an acid. In the compound represented by the general formula (6), examples of the monovalent organic group introduced as R ¹¹ or R ¹² include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and s-butyl. , An alkyl group such as t-butyl, and a substituted or unsubstituted alicyclic group or heterocyclic group such as cyclohexyl, piperidyl, and pyranine.

Examples of the divalent substituent Y include, for example,
Unsaturated aliphatic groups such as ethylene, propylene and butylene; and substituted or unsubstituted alicyclic groups or heterocyclic groups such as cyclohexane, pyrazine, pyran, and morpholane.

It should be noted that the product after decomposition having a substituent and a functional group capable of decomposing in the presence of an acid is-(C = O) O-, -OS (= O) by the action of an alkaline solution. _2- ,
Alternatively, when a dissolution inhibitor such as a compound which produces —O— is further contained, it is contained in an amount of 1 to 60 mol% based on the base resin.
Is preferred. If it deviates from this range, there may be a problem in coatability. In this case, the base resin component used does not have to include a group that is decomposed by an acid.

On the other hand, when the photosensitive material of the present invention is used as a negative chemically amplified resist, for example, a vinyl-based or general formula (5) containing a structure represented by the general formula (1) is used. A photo-acid generator and a photo-crosslinking agent are added to a copolymer of the acrylic compound represented by the formula (4) and an acrylic-soluble or vinyl-based compound represented by the general formula (5) which is soluble in methacrylic acid or acrylic acid. It can be added and prepared.

In this case, as the photo-acid generator, in addition to those enumerated in the case of the positive type, halogenated alkyl-substituted triazine, naphthyridine compound and the like can be used. Further, the compounds shown in Table 3 below and Chemical Formula 46 may be used.

[0103]

[Table 3]

[0104]

[Chemical formula 46] Further, an oxadiazole derivative substituted with a trihalomethyl group represented by the following Chemical Formula 47 and an s-triazine derivative substituted with a trihalomethyl group represented by the following Chemical Formula 48 can also be used.

[0105]

[Chemical 47]

[0106]

[Chemical 48] As the photocrosslinking agent, for example, vinyl having an epoxy group in a side chain, an acrylic polymer represented by the general formula (5); methylol-substituted triazine, melamine-based compounds such as naphthyridine compounds, and the like are used. You can

The photosensitive material of the present invention as a chemically amplified resist has been described above, but when used as a chemically amplified resist, the polymer contained therein preferably satisfies the following conditions. . That is, the softening point is 20
℃ or more and an average molecular weight of 500 to 500,0
00. If the softening point of the resin component of the photosensitive material is too low, that is, lower than 20 ° C., the acid generated from the photo-acid generator by the irradiation of actinic radiation is diffused more than necessary in the resist layer by the baking treatment. Therefore, the resolution of the resist after patterning may decrease.

If the polymer is too high,
When a resist composition containing this is irradiated with electron radiation, the crosslinking reaction is accelerated by the irradiation and baking after irradiation. Therefore, in the case of a positive type resist, the image quality or sensitivity of the resist may deteriorate. On the other hand, if the molecular weight of the polymer is too small, it becomes difficult to form a resist layer having sufficient mechanical strength.

Next, a preparation example of the photosensitive material of the present invention and a pattern forming method using the same will be described by taking a positive chemically amplified resist as an example.

When the photosensitive material of the present invention is used as a chemically amplified resist, the above polymer, a compound which is decomposed by an acid if necessary, that is, a dissolution inhibitor, and a compound which generates an acid when irradiated with actinic radiation are used. That is, it can be prepared by dissolving a photo-acid generator and an organic solvent in an organic solvent and filtering.

When the photosensitive material of the present invention is used as a conventional resist, for example, the above-mentioned polymer and a photosensitizer or a photocrosslinking agent or a photomain chain-breaking agent whose solubility is improved or reduced by exposure are used. It can be prepared by dissolving in a solvent and filtering. Examples of the organic solvent include ketone solvents such as cyclohexanone, acetone, methylethylketone, and methylisobutylketone; methylcellosolve, 2-ethoxyethylacetate, 2-methoxyethylacetate, 2-propoxymethylacetate, or 2- Cellosolve solvent such as butoxyethyl acetate; glycol solvent such as propylene glycol monomethyl ether acetate; ester solvent such as ethyl acetate, butyl acetate or isoamyl acetate; lactone solvent such as γ-butyrolactone; dimethyl sulfoxide, hexamethyl Examples of the nitrogen-containing solvent include phosphoric triamide dimethylformamide and N-methylpyrrolidone. These solvents may be used alone or as a mixed solvent. Furthermore, aromatic solvents such as xylene and toluene, or aliphatic alcohols such as isopropyl alcohol, ethyl alcohol, methyl alcohol, butyl alcohol, n-butyl alcohol, s-butyl alcohol, t-butyl alcohol and isobutyl alcohol are added to these. It may contain an appropriate amount.

In addition to the above-mentioned components, if necessary, a surfactant as a coating film modifying agent; other polymers such as epoxy resin, polymethylmethacrylate, propylene oxide-ethylene oxide copolymer, polystyrene; or You may mix | blend the dye as an antireflection agent.

A process for forming a resist pattern using the photosensitive material of the present invention prepared as described above will be described.

First, a solution of a photosensitive material prepared by dissolving the above components in an organic solvent is coated on a substrate by a spin coating method or a dipping method, and then at about 150 ° C. or lower, preferably 70 to 120 ° C. After drying, a photosensitive resin layer (resist film) containing the above composition as a main component is formed. The substrate used here is, for example, a silicon wafer, a silicon wafer having a step on which various insulating films and electrodes, and wiring are formed, a blank mask, GaAs, AlG.
Examples thereof include III-V group compound semiconductor wafers such as aAs.

Then, the resist film is subjected to pattern exposure, that is, irradiation with actinic radiation is performed through a predetermined mask pattern. As the actinic radiation used for this pattern exposure, short-wavelength ultraviolet rays are usually used.
Electron beam, X-ray, low-pressure mercury lamp light, KrF or ArF excimer laser light, synchrotron orbital radiation light, γ-ray, or ion beam may be used.

Subsequently, the resist film after exposure is heated to 150 ° C. by using a hot plate, an oven or the like, or by irradiating infrared rays.
Baking is performed by heat treatment below.

Then, the resist film after baking is subjected to a developing treatment by an immersion method, a spray method or the like using an alkaline aqueous solution to form a desired pattern. As the alkaline aqueous solution used as the developing solution, for example, an organic alkaline aqueous solution such as tetramethylammonium hydroxide aqueous solution or an inorganic alkaline aqueous solution such as potassium hydroxide or sodium hydroxide may be used at a concentration of 15% or less. You can Further, as a developing solution, isopropyl alcohol, ethanol, methanol, 1-
Organic solvents such as butanol, 2-butanol, 1-methyl-1-propanol, and 1-methyl-2-propanol can also be used. This may be used alone or as a mixed solvent.

After the development treatment, the substrate and the resist film may be rinsed with water or the like.

[0119]

The present inventors have found that a compound having a terpenoid skeleton exhibits excellent dry etching resistance despite having no aromatic ring. The present invention has been made based on such knowledge.

Since the compound having a terpenoid skeleton does not have an aromatic ring, it is originally a KrF excimer laser beam, A
It has low absorption in the short wavelength region such as rF excimer laser light and has excellent transparency.

Since it contains a compound having such a terpenoid skeleton, it can be exposed to ultraviolet light, deep UV light, 2
48 nm KrF excimer laser light, 193 nm Ar
A photosensitive material having excellent transparency with respect to short wavelength light such as F-xima laser light, electron beam, and X-ray, and having sufficient dry etching resistance was obtained. By using the photosensitive material of the present invention having such characteristics, a quarter micron pattern can be accurately formed.

In particular, when a compound containing a menthyl group or a menthyl derivative group is used as the compound,
A photosensitive material having excellent dry etching resistance can be obtained. It is considered that the menthyl group and the like have a ring structure and therefore, even if one carbon-carbon bond is broken, the other bond remains. Further, the effect based on the compound containing a menthyl group or a menthyl derivative group being chiral,
It is also considered that there is a steric effect due to the presence of an alkyl substituent such as an isopropyl group or a methyl group on the menthyl group. Furthermore, the presence of substituents contributes more to stabilization of the ring conformation, which is also considered to have an effect.

Terpenes are naturally-occurring compounds with high safety, which are also used as raw materials for flavors, foods, pharmaceuticals and the like. Therefore, even when the above compound is used as a polymer, the compound after decomposition becomes a terpene, so that a photosensitive material excellent in safety can be obtained.

[0124]

The present invention will be described in more detail below with reference to examples. Note that these examples do not limit the present invention. (Example I) In this example, a resin component containing a compound having a terpenoid skeleton was used, and a photosensitive material containing this resin component was produced and evaluated. In particular, changing the type of compound having a terpenoid skeleton,
The resin component was synthesized. (Synthesis Example I-1) 24 g of methacrylic acid, 31 g of citronellol, and 15 g of paratoluenesulfonic acid were heated and refluxed at an oil temperature of 150 ° C. for 19 hours in 500 mL of toluene. Then, the reaction was stopped with a saturated sodium hydrogen carbonate aqueous solution, and ether was added. The two layers were separated, the aqueous layer was extracted with ether, and the organic layers were combined and washed with a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium hydroxide solution to remove the acid. Furthermore, the pH was adjusted to 7 with a saturated aqueous solution of ammonium chloride, and dried with saturated saline and anhydrous sodium sulfate. Finally, the obtained oily substance was distilled under reduced pressure to obtain citronellyl methacrylate. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-1) 2.1 g of citronellyl methacrylate and 0.4 g of azoisobutyronitrile as a polymerization initiator were dissolved in 6 mL of toluene.

The obtained solution was frozen in liquid nitrogen, deaerated three times for 20 minutes, and then brought to room temperature. Then, under a nitrogen stream, the oil temperature was heated at 70 ° C for 16 hours to obtain 600 m of methanol
The reaction was stopped by L. After reprecipitation with methanol, it was filtered off and the solvent was distilled off under vacuum to obtain polycitronellyl methacrylate.

This was made into a cyclohexanone solution, which was then applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined.

Furthermore, carbon tetrafluoride (CF
₄ ) The etching rate by gas was measured. The dry etching resistance was evaluated under the following conditions. That is, the flow rate of CF ₄ was 12.6 sccm, the degree of vacuum was 10 mtorr, and the microwave output was 150 W.

Further, instead of polycitronellyl methacrylate, novolac resin and polymethylmethacrylate were each made into a cyclohexanone solution to prepare Comparative Examples (I-1) and (I-2).

The obtained solutions of Comparative Example (I-1) and Comparative Example (I-2) were coated on a quartz wafer in the same manner, and A
The transparency to rF excimer laser light was examined. Furthermore,
The etching rate with carbon tetrafluoride gas was examined under the same conditions. The results obtained are summarized in Table 4 below. ． The etching rate of polycitronellyl methacrylate was 0.3 when the etching rate of PMMA was 1.

[0130]

[Table 4] As shown in Table 4, the polymer having a terpenoid skeleton has a high transmittance at 193 nm and an excellent dry etching property. On the other hand, it can be seen that the novolac resin has a remarkably low transmittance and PMMA has poor etching resistance. Hereinafter, (Example I-1) to (Example I)
In -3), each of the copolymers containing citronellyl methacrylate obtained in Synthesis Example 1 was synthesized, a photosensitive material containing the same was obtained, and its characteristics were investigated. (Example I-1) 9 g of citronellyl methacrylate, 1 g of glycidyl methacrylate, and 0.5 g of azoisobutyronitrile as a polymerization initiator were added to 30 m of toluene.
Dissolved in L.

The obtained solution was frozen in liquid nitrogen, degassed three times for 20 minutes, and then brought to room temperature. Next, the mixture was heated at an oil temperature of 70 ° C for 16 hours under a nitrogen stream, and the reaction was stopped with methanol. After reprecipitation with methanol, the mixture was filtered off and the solvent was distilled off under vacuum to obtain the target copolymer.

1 g of the obtained copolymer was dissolved in 9 mL of methyl 3-methoxypropionate, the solution was applied on a silicon wafer to a thickness of 1 μm, and then prebaked at 100 ° C. Then, electron beam exposure (exposure amount 10
μCcm ⁻² , 20 keV) and then developed with methyl ethyl ketone to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-2) 9 g of citronellyl methacrylate, 1 g of allyl methacrylate, and 0.5 g of azoisobutyronitrile as a polymerization initiator were dissolved in 30 mL of toluene.

The obtained solution was frozen with liquid nitrogen, deaerated 5 times for 20 minutes, and then brought to room temperature. Next, the mixture was heated at an oil temperature of 70 ° C for 16 hours under a nitrogen stream, and the reaction was stopped with methanol. After reprecipitation with methanol, the mixture was filtered off and the solvent was distilled off under vacuum to obtain the target copolymer.

The resulting copolymer was prepared according to the above-mentioned Example (I-
After coating on a silicon wafer as a solution similar to 1), prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined. As a result, 0.
A negative line and space pattern of 5 μm could be resolved. (Example I-3) Citronellyl methacrylate 5 g, α
5 g of chlorotrifluoroethyl acrylate and 0.5 g of azoisobutyronitrile as a polymerization initiator
Is tetrahydrofuran (hereinafter abbreviated as THF) 28
Dissolved in mL.

The obtained solution was frozen in liquid nitrogen, degassed 5 times for 20 minutes and then brought to room temperature. Next, the mixture was heated under a nitrogen stream at an oil temperature of 60 ° C. for 16 hours, and the reaction was stopped with hexane. After reprecipitation with hexane, the product was filtered off and the solvent was distilled off under vacuum to obtain a target copolymer.

The resulting copolymer was prepared according to the above-mentioned Example (I-
After being coated on a silicon wafer as a solution similar to 1), prebaking and exposure were performed under the same conditions, and further development was performed using methyl isobutyl ketone to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm positive line and space pattern could be resolved. (Synthesis Example I-2) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-1) was synthesized, and the copolymer was evaluated.

Citronellyl methacrylate, t-butyl methacrylate, and methacrylic acid were added at 50:30:20.
Was dissolved in 40 mL of THF together with 0.5 g of azoisobutyronitrile as a polymerization initiator.

The obtained solution was frozen in liquid nitrogen, deaerated 5 times for 20 minutes, and then brought to room temperature. Next, the mixture was heated at an oil temperature of 60 ° C. for 9 hours under a nitrogen stream, and the reaction was stopped with hexane. After reprecipitation with hexane, the mixture was filtered and the solvent was removed under vacuum to obtain the target copolymer.

The obtained copolymer was made into a cyclohexanone solution, which was coated on a quartz wafer to a film thickness of 1 μm, and then ArF
As a result of examining the transparency with respect to the excimer laser beam (193 nm), the transmittance was 74%, which was superior to PMMA.

Further, as a result of comparing the etching rate with carbon tetrafluoride gas (CF ₄ ) gas with PMMA, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3.

The dry etching resistance was evaluated under the following conditions. In other words, the flow rate of CF ₄ is 12.6 sccm, the degree of vacuum is 10 mtorr,
The microwave output was 150 W.

The following (Example I-4) to (Example I-1)
In 1), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-2) was synthesized, and its characteristics were examined. (Example I-4) 2 g of the copolymer obtained in Synthesis Example (I-2) and 0.04 g of triphenylsulfonium triflate as an acid generator were dissolved in 8 mL of 2-ethoxyethyl acetate.

This was applied on a silicon wafer in a film thickness of 0.8 μm and then prebaked at 100 ° C. Then
After ArF excimer laser exposure (40 mJcm ⁻² ), development was performed with an aqueous solution of tetramethylammonium hydroxide to form a pattern and its characteristics were examined. As a result, a line and space of 0.15 μm could be resolved.

Further, in the same manner as in Synthesis Example (I-1),
When the transparency and the dry etching resistance were evaluated, the transmittance was 60% and the etching rate was 0.3, which was excellent with respect to PMMA. (Example I-5) to (Example I-7) Using the photo-acid generator shown in Table 5 below, the above-mentioned Example (I-) was used.
After coating on a silicon wafer in the same manner as 4), prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined. In each example,
The amount of acid generator added was 0.05 g each. Further, the transparency and the dry etching resistance were evaluated in the same manner as in Synthesis Example (I-1). The results are also shown in Table 5 below. The etching rate is a value for PMMA.

[0147]

[Table 5] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-8) 2 g of the copolymer obtained in Synthesis Example (I-2), 0.04 g of triphenylsulfonium triflate as a photoacid generator, and 3, as a dissolution inhibitor.
0.1 g of 3-bis-4'-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone was added to 2 g.
-Ethoxyethyl acetate dissolved in 8 mL.

This was applied on a silicon wafer to a film thickness of 0.8 μm and then prebaked at 100 ° C. Then
After ArF excimer laser exposure (40 mJcm ⁻² ), development was performed with an aqueous solution of tetramethylammonium hydroxide to form a pattern and its characteristics were examined. As a result, a line and space of 0.15 μm could be resolved.

Further, in the same manner as in Synthesis Example (I-1),
When the transparency and the dry etching resistance were evaluated, the transmittance was 55%, and the etching rate was excellent with respect to PMMA of 0.3. (Example I-9) to (Example I-11) Using the photo-acid generator shown in Table 6 below, the above-mentioned Example (I-) was used.
After coating on a silicon wafer in the same manner as in 8), prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined. In each example, the amount of the photo-acid generator added was 0.05 g.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The results are also shown in Table 6 below. The etching rate is PM
It is a value for MA.

[0151]

[Table 6] In each of the examples, a line and space pattern of 0.15 μm could be obtained.

In the present invention, the monomer represented by the general formula (2), t-butyl methacrylate (functional group decomposable by acid), and methacrylic acid (alkali-soluble group) are the same as those shown in FIG. Within the shaded area, it is possible to mix in any composition ratio. (Synthesis Example I-3) A pinocamphyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of pinocampheol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-3) Other than using pinocamphyl methacrylate,
Polypinocamphyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) described above, and this was used as the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polypinocamphylmethacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polypinocamphyl methacrylate is 0.3 when the etching rate of PMMA is 1. there were.

Hereinafter, (Example I-12) to (Example I-)
In 14), each of the copolymers containing the pinocamphyl methacrylate obtained in Synthesis Example (I-3) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-12) Instead of the citronellyl methacrylate, the pinocamphyl methacrylate obtained in the above-mentioned synthesis example (I-3) is used, but the above-mentioned example (I-) is used.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-13) The above-mentioned Example (I-) was carried out except that the pinocamphyl methacrylate obtained in the above-mentioned Synthesis Example (I-3) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-14) The above-mentioned Example (I-) was carried out except that the pinocamphyl methacrylate obtained in the above-mentioned Synthesis Example (I-3) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-4) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-3) was synthesized, and the copolymer was evaluated.

Specifically, the copolymer obtained by synthesizing the copolymer in the same manner as in the above-mentioned Synthesis Example (I-2) except that pinocamphyl methacrylate was used instead of citronellyl methacrylate. Was the same cyclohexanone solution as described above. ArF excimer laser light (193 nm)
As a result of similarly examining the transparency with respect to
%, Which was superior to PMMA.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-15) to (Example I-)
In 22), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-4) was synthesized, and its characteristics were examined. (Example I-15) to (Example I-18) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-4) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 7 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0165]

[Table 7] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-19) to (Example I-22) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-4) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 8 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0167]

[Table 8] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-5) Geranyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of geraniol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-5) Polygeranyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that geranyl methacrylate was used. A cyclohexanone solution similar to the above was used. ArF excimer laser light (193
Similarly, the transparency for polygeranyl methacrylate was 45 μm and the transmittance was 45 μm.
%Met.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polygeranyl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-23) to (Example I-)
In 25), each of the copolymers containing geranyl methacrylate obtained in Synthesis Example (I-5) was synthesized, a photosensitive material containing the copolymer was obtained, and the characteristics thereof were examined. (Example I-23) Copolymerization was performed in the same manner as in the above-mentioned Example (I-1) except that the geranyl methacrylate obtained in the above-mentioned Synthesis Example (I-5) was used in place of the citronellyl methacrylate. The coalescence was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-24) Copolymerization was carried out in the same manner as in the above-mentioned Example (I-2) except that the geranyl methacrylate obtained in the above-mentioned Synthesis Example (I-5) was used in place of the citronellyl methacrylate. The coalescence was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-25) Copolymerization was carried out in the same manner as in the above-mentioned Example (I-3) except that the geranyl methacrylate obtained in the above-mentioned Synthesis Example (I-5) was used instead of the citronellyl methacrylate. The coalescence was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-6) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-5) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that geranyl methacrylate was used instead of citronellyl methacrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-26) to (Example I-)
In 33), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-6) was synthesized, and its characteristics were examined. (Example I-26) to (Example I-29) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-6) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 9 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0181]

[Table 9] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-30) to (Example I-33) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-6) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 10 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0183]

[Table 10] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis example I-7) The above-mentioned synthesis example (I-1) except that citronellol is replaced with the same amount of fentyl alcohol.
Fentyl methacrylate was obtained in the same manner as in. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-7) Polyphentyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that fentyl methacrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (1
When the transparency to (93 nm) was similarly examined,
The transmittance of polyphentyl methacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyphentyl methacrylate was 0.
It was 3.

Hereinafter, (Example I-34) to (Example I-)
In 36), each of the copolymers containing fentyl methacrylate obtained in Synthesis Example (I-7) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-34) The above-mentioned Example (I-1) except that the fentyl methacrylate obtained in the above-mentioned Synthesis Example (I-7) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that of Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-35) The above-mentioned Example (I-2) is used except that the fentyl methacrylate obtained in the above-mentioned Synthesis Example (I-7) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-36) The above-mentioned Example (I-3) except that the fentyl methacrylate obtained in the above-mentioned Synthesis Example (I-7) is used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-8) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-7) was synthesized, and the copolymer was evaluated.

Specifically, except that fentyl methacrylate is used instead of citronellyl methacrylate,
A copolymer was synthesized in the same manner as in Synthesis Example (I-2) above, and the obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-37) to (Example I-)
In 44), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-8) was synthesized, and its characteristics were investigated. (Example I-37) to (Example I-40) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-8) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 11 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0197]

[Table 11] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-41) to (Example I-44) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-8) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 12 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0199]

[Table 12] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-9) Neryl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of nerol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-9) Polyneryl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that neryl methacrylate was used. A cyclohexanone solution similar to the above was used. ArF excimer laser light (193n
When the transparency to m) was examined in the same manner, the transmittance of polyneryl methacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyneryl methacrylate was 0.3 when the etching rate of PMMA was 1. .

Hereinafter, (Example I-45) to (Example I-)
In 47), the copolymers containing neryl methacrylate obtained in Synthesis Example (I-9) were synthesized, and a photosensitive material containing them was obtained, and the characteristics thereof were examined. (Example I-45) Copolymerization was performed in the same manner as in the above-mentioned Example (I-1) except that the neryl methacrylate obtained in the above-mentioned Synthesis Example (I-9) was used instead of the citronellyl methacrylate. The coalescence was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that of Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-46) Copolymerization was carried out in the same manner as in the above-mentioned Example (I-2) except that the neryl methacrylate obtained in the above-mentioned Synthesis Example (I-9) was used instead of the citronellyl methacrylate. The coalescence was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-47) Copolymerization was performed in the same manner as in the above-mentioned Example (I-3) except that the neryl methacrylate obtained in the above-mentioned Synthesis Example (I-9) was used instead of the citronellyl methacrylate. The coalescence was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-10) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-9) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in the above Synthesis Example (I-2) except that neryl methacrylate was used instead of citronellyl methacrylate, and the obtained copolymer was used in the same manner. Of cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-48) to (Example I-)
In 55), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-10) was synthesized, and its characteristics were examined. (Example I-48) to (Example I-51) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-10) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 13 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0213]

[Table 13] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-52) to (Example I-55) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-10) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 14 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0215]

[Table 14] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-11) Bornyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronetol was replaced with the same amount of borneol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-11) Polybornyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except for using bornyl methacrylate. Was the same cyclohexanone solution as described above. ArF excimer laser light (19
Similarly, the transparency of polybornyl methacrylate was found to be 4 μm in terms of 1 μm.
It was 5%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polybornyl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-56) to (Example I-)
In 58), each of the copolymers containing bornyl methacrylate obtained in Synthesis Example (I-11) was synthesized, a photosensitive material containing the copolymer was obtained, and the characteristics thereof were examined. (Example I-56) The above-mentioned Example (I-1) except that the bornyl methacrylate obtained in the above-mentioned Synthesis Example (I-11) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that of Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-57) The above-mentioned Example (I-2) except that the bornyl methacrylate obtained in the above-mentioned Synthesis Example (I-11) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-58) The above-mentioned Example (I-3) except that the bornyl methacrylate obtained in the above-mentioned Synthesis Example (I-11) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-12) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-11) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that bornyl methacrylate was used instead of citronellyl methacrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Furthermore, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-59) to (Example I-)
In 66), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-12) was synthesized, and its characteristics were examined. (Example I-59) to (Example I-62) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-12) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 15 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0229]

[Table 15] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-63) to (Example I-66) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-12) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 16 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0231]

[Table 16] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-13) Cineryl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of cinerol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-13) Polycineryl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that cineryl methacrylate was used. The same cyclohexanone solution as described above was used. ArF excimer laser light (19
(3 nm), the transparency was similarly examined, and it was found that the transmittance of polycineryl methacrylate was 1 μm.
It was 5%.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polycineryl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-67) to (Example I-)
In 69), each of the copolymers containing cineryl methacrylate obtained in Synthesis Example (I-13) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-67) The above-mentioned Example (I-1) except that the cyneryl methacrylate obtained in the above-mentioned Synthesis Example (I-13) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-68) The above-mentioned Example (I-2) except that the cyneryl methacrylate obtained in the above-mentioned Synthesis Example (I-13) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-69) The above-mentioned Example (I-3) except that the cyneryl methacrylate obtained in the above-mentioned Synthesis Example (I-13) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-14) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-13) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that cyneryl methacrylate was used instead of citronellyl methacrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-70) to (Example I-)
In 77), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-14) was synthesized, and its characteristics were examined. (Example I-70) to (Example I-73) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-14) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 17 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0245]

[Table 17] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-74) to (Example I-77) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-14) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 18 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0247]

[Table 18] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-15) Pinyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of pinol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-15) Polypinyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that pinyl methacrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193n
When the transparency to m) was examined in the same manner, the transmittance of polypinyl methacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polypinylmethacrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-78) to (Example I-)
In 80), each of the copolymers containing pinyl methacrylate obtained in Synthesis Example (I-15) was synthesized, a photosensitive material containing the copolymer was obtained, and the characteristics thereof were examined. (Example I-78) The same procedure as in Example (I-1) above was repeated except that the pinyl methacrylate obtained in Synthesis Example (I-15) above was used instead of citronellyl methacrylate. A polymer was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-79) The same procedure as in Example (I-2) was repeated except that the pinyl methacrylate obtained in Synthesis Example (I-15) was used instead of citronellyl methacrylate. A polymer was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-80) The same procedure as in Example (I-3) above was repeated except that the pinyl methacrylate obtained in Synthesis Example (I-15) above was used instead of citronellyl methacrylate. A polymer was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-16) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-15) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that pinyl methacrylate was used instead of citronellyl methacrylate, and the obtained copolymer was The same cyclohexanone solution was used.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-81) to (Example I-)
88), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-16) was synthesized, and its characteristics were investigated. (Example I-81) to (Example I-84) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-16) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 19 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0261]

[Table 19] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-85) to (Example I-88) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-16) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 20 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0263]

[Table 20] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-17) Ascaridyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of ascaridol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-17) Other than using ascaridyl methacrylate,
Polyalkali dimethacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) described above, and this was used as the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polyascaridyl methacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyascalydyl methacrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-89) to (Example I-)
In 91), the copolymers containing ascalydyl methacrylate obtained in Synthesis Example (I-17) were synthesized, and photosensitive materials containing the same were obtained, and their properties were examined. (Example I-89) The above-mentioned Example (I-) was carried out except that the ascaridyl methacrylate obtained in the above-mentioned Synthesis Example (I-17) was used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-90) The above-mentioned Example (I-) is used except that the ascaridyl methacrylate obtained in the above-mentioned Synthesis Example (I-17) is used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-91) The above-mentioned example (I-) was performed except that the ascaridyl methacrylate obtained in the above-mentioned synthesis example (I-17) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm positive line and space pattern could be resolved. (Synthesis Example I-18) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-17) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in the above Synthesis Example (I-2) except that ascaridyl methacrylate was used instead of citronellyl methacrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-92) to (Example I-92)
In 99), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-18) was synthesized, and its characteristics were examined. (Example I-92) to (Example I-95) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-18) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 21 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0277]

[Table 21] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-96) to (Example I-99) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-18) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 22 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0279]

[Table 22] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-19) Farnesyl methacrylate was obtained in the same manner as in Synthesis Example (I-1) above except that citronellol was replaced with the same amount of farnesol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-19) Other than using farnesyl methacrylate,
Polyfarnesyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) described above, and this was used as the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polyfarnesyl methacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyfarnesyl methacrylate was 0.3 when the etching rate of PMMA was 1. .

Hereinafter, (Example I-100) to (Example I)
-102), each of the farnesyl methacrylate-containing copolymers obtained in Synthesis Example (I-19) was synthesized, and a photosensitive material containing the same was obtained, and its properties were examined. (Example I-100) The above-mentioned Example (I) is repeated except that the farnesyl methacrylate obtained in the above-mentioned Synthesis Example (I-19) is used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in -1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-101) The above-mentioned Example (I) was repeated except that the farnesyl methacrylate obtained in the above-mentioned Synthesis Example (I-19) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in -2).

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-102) The above-mentioned Example (I) was repeated except that the farnesyl methacrylate obtained in the above-mentioned Synthesis Example (I-19) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in -3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-20) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-19) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that farnesyl methacrylate was used instead of citronellyl methacrylate, and the obtained copolymer was treated in the same manner. Of cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-103) to (Example I)
-110), the chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-20) was synthesized, and its characteristics were investigated. (Example I-103) to (Example I-106) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-20) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 23 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0293]

[Table 23] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-107) to (Example I-110) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-20) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 24 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0295]

[Table 24] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-21) The above Synthesis Example (I-1) except that citronellol is replaced with the same amount of patchouli alcohol.
In the same manner as described above, patchuryl methacrylate was obtained. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-21) Polypatchuryl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that patchoulyl methacrylate was used. Was the same cyclohexanone solution as described above. When the transparency to the ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polypaturyl methacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polypataturyl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

[Examples I-111] to (Example I)
-113), each of the copolymers containing patchoulyl methacrylate obtained in Synthesis Example (I-21) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-111) The above-mentioned Example (I-111) was used except that the patchuryl methacrylate obtained in the above-mentioned Synthesis Example (I-21) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-112) The above-mentioned Example (I-) was carried out except that the patchuryl methacrylate obtained in the above-mentioned Synthesis Example (I-21) was used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-113) The above-mentioned Example (I-) was used except that the patchuryl methacrylate obtained in the above-mentioned Synthesis Example (I-21) was used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm positive line and space pattern could be resolved. (Synthesis Example I-22) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-21) was synthesized, and the copolymer was evaluated.

Specifically, except that patchuryl methacrylate is used instead of citronellyl methacrylate,
A copolymer was synthesized in the same manner as in Synthesis Example (I-2) above, and the obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Furthermore, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-114) to (Example I)
In -121), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-22) was synthesized, and its characteristics were examined. (Example I-114) to (Example I-117) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-22) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 25 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0309]

[Table 25] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-118) to (Example I-121) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-22) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 26 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0311]

[Table 26] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-23) Neroridyl methacrylate was obtained in the same manner as in Synthesis Example (I-1) above except that citronellol was replaced with the same amount of nerolidol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-23) Polynerolidyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that nerolidyl methacrylate was used. Was the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polynerolidyl methacrylate was 45% in terms of 1 μm. Furthermore, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polynerolidyl methacrylate was 0.3 when the etching rate of PMMA was 1.

Hereinafter, (Example I-122) to (Example I)
-124), each of the copolymers containing nerolidyl methacrylate obtained in Synthesis Example (I-23) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-122) The above-mentioned Example (I-) was used except that the nerolidyl methacrylate obtained in the above-mentioned Synthesis Example (I-23) was used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-123) In place of the citronellyl methacrylate, the above-mentioned Example (I-) is used except that the nerolidyl methacrylate obtained in the above-mentioned Synthesis Example (I-23) is used.
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-124) The above-mentioned Example (I-) is used except that the nerolidyl methacrylate obtained in the above-mentioned Synthesis Example (I-23) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-24) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-23) was synthesized, and the copolymer was evaluated.

Specifically, except that nerolidyl methacrylate is used instead of citronellyl methacrylate,
A copolymer was synthesized in the same manner as in Synthesis Example (I-2) above, and the obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-125) to (Example I)
-132), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-24) was synthesized, and its characteristics were investigated. (Example I-125) to (Example I-128) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-24) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 27 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0324]

[Table 27] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-129) to (Example I-132) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-24) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 28 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0326]

[Table 28] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-25) Carotyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of carotol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-25) Polycarotyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that carotyl methacrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (19
Similarly, the transparency for polycarotylmethacrylate was 45 μm and the transmittance was 45 μm.
%Met.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polycarotyl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-133) to (Example I)
-135), each of the copolymers containing carotyl methacrylate obtained in Synthesis Example (I-25) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-133) In place of the citronellyl methacrylate, the carotyl methacrylate obtained in the above-mentioned synthesis example (I-25) is used, but in the above-mentioned example (I-
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-134) In place of the citronellyl methacrylate, the carotyl methacrylate obtained in the above Synthesis Example (I-25) is used, but in the above Example (I-
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-135) In place of the citronellyl methacrylate, the carotyl methacrylate obtained in the above Synthesis Example (I-25) is used, but in the above Example (I-
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-26) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-25) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in the above Synthesis Example (I-2) except that carotyl methacrylate was used instead of citronellyl methacrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate by carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-136) to (Example I)
-143), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-26) was synthesized, and its characteristics were examined. (Example I-136) to (Example I-139) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-26) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 29 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0340]

[Table 29] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-140) to (Example I-143) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-26) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 30 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0342]

[Table 30] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-27) A cazinyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of casino. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-27) Polycadinyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that cazinyl methacrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (19
(3 nm), the transparency was similarly examined, and it was found that the transmittance of polycazinyl methacrylate was 45 in terms of 1 μm.
%Met.

Further, as a result of measuring the etching rate by carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polycazinyl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-144) to (Example I)
-146), the copolymers containing carotyl methacrylate obtained in Synthesis Example (I-27) were synthesized, and photosensitive materials containing the same were obtained, and their properties were examined. (Example I-144) In place of the citronellyl methacrylate, the above-mentioned example (I-) is used except that the cazinyl methacrylate obtained in the above-mentioned synthesis example (I-27) is used.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-145) The above-mentioned Example (I-) is used except that the cazinyl methacrylate obtained in the above-mentioned Synthesis Example (I-27) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-146) In place of the citronellyl methacrylate, the above-mentioned example (I- except that the cazinyl methacrylate obtained in the above-mentioned synthesis example (I-27) is used.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-28) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-27) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that cazinyl methacrylate was used instead of citronellyl methacrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-147) to (Example I)
-154), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-28) was synthesized, and its characteristics were examined. (Example I-147) to (Example I-150) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-28) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 31 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0356]

[Table 31] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-151) to (Example I-154) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-28) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 32 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0358]

[Table 32] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-29) Lancil methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of lanseol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-29) Polylansyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that lanyl methacrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (19
(3 nm), the transparency was similarly examined.
%Met.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polylansyl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-155) to (Example I)
-157), each of the copolymers containing lanyl methacrylate obtained in Synthesis Example (I-29) was synthesized, a photosensitive material containing the copolymer was obtained, and the characteristics thereof were examined. (Example I-155) In place of the citronellyl methacrylate, the above-mentioned example (I- except that the lanyl methacrylate obtained in the above-mentioned synthesis example (I-29) is used.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that of Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-156) The above-mentioned Example (I-) was carried out except that the lanyl methacrylate obtained in the above-mentioned Synthesis Example (I-29) was used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-157) The above-mentioned Example (I-) was conducted except that the lanyl methacrylate obtained in the above-mentioned Synthesis Example (I-29) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-30) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-29) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above, except that lanyl methacrylate was used instead of citronellyl methacrylate.
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-158) to (Example I)
-165), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-30) was synthesized, and its characteristics were examined. (Example I-158) to (Example I-161) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-30) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 33 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0372]

[Table 33] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-162) to (Example I-165) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-30) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 34 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0374]

[Table 34] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-31) Oydesmil methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of eudesmol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-31) Other than using eudesmil methacrylate,
Polyeudesmil methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) described above, and this was used as the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polyoidesyl methacrylate was 45% in terms of 1 μm.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyoidesylmethacrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-166) to (Example I)
-168), each of the copolymers containing eudesmil methacrylate obtained in Synthesis Example (I-31) was synthesized, and a photosensitive material containing the same was obtained, and its properties were examined. (Example I-166) The above-mentioned Example (I) was carried out except that the eudesmil methacrylate obtained in the above-mentioned Synthesis Example (I-31) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in -1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-167) In place of the citronellyl methacrylate, the above-mentioned example (I) is used except that the eudesmil methacrylate obtained in the above-mentioned synthesis example (I-31) is used.
A copolymer was synthesized in the same manner as in -2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-168) In place of the citronellyl methacrylate, the above-mentioned example (I) is used except that the eudesmil methacrylate obtained in the above-mentioned synthesis example (I-31) is used.
A copolymer was synthesized in the same manner as in -3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-32) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-31) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that eudesmil methacrylate was used in place of citronellyl methacrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-169) to (Example I)
-176), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-32) was synthesized, and its characteristics were investigated. (Example I-169) to (Example I-172) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-32) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 35 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0388]

[Table 35] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-173) to (Example I-176) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-32) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 36 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0390]

[Table 36] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-33) A cedryl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of sedrol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-33) Polycedryl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that ceryl methacrylate was used. This was used as the same cyclohexanone solution as described above. ArF excimer laser light (1
When the transparency to (93 nm) was similarly examined,
The transmittance of polycedryl methacrylate in terms of 1 μm is 4
It was 5%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polycedryl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

[Examples I-177] to [Example I]
-179), each of the copolymers containing the cerylyl methacrylate obtained in Synthesis Example (I-33) was synthesized, and a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-177) In place of the citronellyl methacrylate, the above-mentioned Example (I-) is used except that the cedolyl methacrylate obtained in the above Synthesis Example (I-33) is used.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-178) In place of the citronellyl methacrylate, the above-mentioned Example (I-) is used except that the cedolyl methacrylate obtained in the above-mentioned Synthesis Example (I-33) is used.
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-179) In place of the citronellyl methacrylate, the above-mentioned Example (I-) is used except that the cedolyl methacrylate obtained in the above-mentioned Synthesis Example (I-33) is used.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-34) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-33) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above, except that cedolyl methacrylate was used instead of citronellyl methacrylate.
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-180) to (Example I)
-187), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-34) was synthesized, and its characteristics were examined. (Example I-180) to (Example I-183) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-34) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The results obtained are summarized in Table 37 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0404]

[Table 37] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-184) to (Example I-187) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-34) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 38 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0406]

[Table 38] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-35) Guayyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of guayol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-35) Polyguayl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that guayle methacrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (19
(3 nm), the transparency was measured in the same manner, and it was found that the polyguanyl methacrylate had a transmittance of 1 μm of 45.
%Met.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyguayl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-188) to (Example I)
-190), each of the copolymers containing guayyl methacrylate obtained in Synthesis Example (I-35) was synthesized, and a photosensitive material containing the copolymer was obtained, and the characteristics thereof were examined. (Example I-188) In place of the citronellyl methacrylate, the guayle methacrylate obtained in the above Synthesis Example (I-35) is used, but the above-mentioned Example (I-) is used.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-189) In place of the citronellyl methacrylate, the guayle methacrylate obtained in the above Synthesis Example (I-35) is used, but in the above Example (I-).
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-190) In place of the citronellyl methacrylate, the guayle methacrylate obtained in the above Synthesis Example (I-35) is used, but in the above Example (I-190).
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-36) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-35) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in the above Synthesis Example (I-2) except that guayl methacrylate was used instead of citronellyl methacrylate.
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied onto a quartz wafer in a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-191) to (Example I)
-198), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-36) was synthesized, and its characteristics were investigated. (Example I-191) to (Example I-194) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-36) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 39 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0420]

[Table 39] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-195) to (Example I-198) The copolymer obtained in Synthesis Example (I-36) is used instead of the copolymer obtained in Synthesis Example (I-2). Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 40 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0422]

[Table 40] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-37) A kesoglycosylmethacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of sessoglycol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-37) Polykessoglycosyl methacrylate is obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) described above except that the sessoglycosyl methacrylate is used. This was used as the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of the poly (glycosyl glycosyl methacrylate) in terms of 1 μm was 45%.

Furthermore, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of the polykessoglycosylmethacrylate is 0.3 when the etching rate of PMMA is 1. there were.

Hereinafter, (Example I-199) to (Example I)
-201), each of the copolymers containing the gesso-glycosyl methacrylate obtained in Synthesis Example (I-37) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-199) In the same manner as in the above-mentioned Example (I-1) except that the quesos glycosyl methacrylate obtained in the above-mentioned Synthesis Example (I-37) was used in place of the citronellyl methacrylate. A copolymer was synthesized.

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-200) In the same manner as in the above-mentioned Example (I-2) except that the quesos glycosyl methacrylate obtained in the above-mentioned Synthesis Example (I-37) was used in place of the citronellyl methacrylate. A copolymer was synthesized.

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-201) In the same manner as in the above-mentioned Example (I-3) except that instead of the citronellyl methacrylate, the Kessos glycosyl methacrylate obtained in the above-mentioned Synthesis Example (I-37) was used. A copolymer was synthesized.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-38) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-37) was synthesized, and the copolymer was evaluated.

Specifically, the copolymer obtained by synthesizing the copolymer in the same manner as in the above-mentioned Synthesis Example (I-2) except that the sessoglycol methacrylate was used in place of the citronellyl methacrylate. Was used as a similar cyclohexanone solution.

This solution was applied onto a quartz wafer in a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Furthermore, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-202) to (Example I)
-209), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-38) was synthesized, and its characteristics were examined. (Example I-202) to (Example I-205) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-38) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 41 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0436]

[Table 41] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-206) to (Example I-209) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-38) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 42 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0438]

[Table 42] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-39) Phytyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of phytol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-39) Polyphytyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that phytyl methacrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (19
(3 nm), the transparency was similarly examined, and it was found that the transmittance of polyphytyl methacrylate was 45 μm in terms of 1 μm.
%Met.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyphytyl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

[Examples I-210] to [Example I]
-212), the copolymers containing phytyl methacrylate obtained in Synthesis Example (I-39) were synthesized, and photosensitive materials containing the same were obtained, and their properties were examined. (Example I-210) In place of the citronellyl methacrylate, the phytyl methacrylate obtained in the above-mentioned synthesis example (I-39) is used, but in the above-mentioned example (I-).
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-211) In place of the citronellyl methacrylate, the phytyl methacrylate obtained in the above synthesis example (I-39) is used, but the above-mentioned example (I-
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-212) The above-mentioned Example (I-) was carried out except that the phytyl methacrylate obtained in the above-mentioned Synthesis Example (I-39) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-40) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-39) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that phytyl methacrylate was used instead of citronellyl methacrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-213) to (Example I)
-220), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-40) was synthesized, and its characteristics were investigated. (Example I-213) to (Example I-216) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-40) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 43 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0452]

[Table 43] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-217) to (Example I-220) The copolymer obtained in Synthesis Example (I-40) is used instead of the copolymer obtained in Synthesis Example (I-2). Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 44 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0454]

[Table 44] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-41) Sucralyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of sclareol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-41) Polysclaryl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that sclaryl methacrylate was used. Was the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polysclaryl methacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polysclaryl methacrylate was 0.
It was 3.

[Examples I-221] to [Example I]
223), each of the copolymers containing sucralyl methacrylate obtained in Synthesis Example (I-41) was synthesized, and a photosensitive material containing the same was obtained, and its properties were examined. (Example I-221) The above-mentioned Example (I-) is used except that the sclaryl methacrylate obtained in the above-mentioned Synthesis Example (I-41) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-222) Instead of citronellyl methacrylate, the sucralyl methacrylate obtained in the above Synthesis Example (I-41) is used, but the above-mentioned Example (I-
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-223) In place of the citronellyl methacrylate, the sucralyl methacrylate obtained in the above Synthesis Example (I-41) is used, but the above-mentioned Example (I-) is used.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-42) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-41) was synthesized, and the copolymer was evaluated.

Specifically, except that sucralyl methacrylate is used instead of citronellyl methacrylate,
A copolymer was synthesized in the same manner as in Synthesis Example (I-2) above, and the obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-224) to (Example I)
-231), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-42) was synthesized, and its characteristics were examined. (Example I-224) to (Example I-227) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-42) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 45 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0468]

[Table 45] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-228) to (Example I-231) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-42) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 46 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0470]

[Table 46] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-43) Manyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of manol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-43) Polymeryl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that manyl methacrylate was used. A cyclohexanone solution similar to the above was used. ArF excimer laser light (193n
When the transparency with respect to m) was examined in the same manner, the transmittance of polymanyl methacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polymanyl methacrylate was 0.3 when the etching rate of PMMA was 1. .

Hereinafter, (Example I-232) to (Example I)
234), the copolymers containing the manyl methacrylate obtained in the above Synthesis Example (I-43) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-232) The above-mentioned Example (I-1) except that the manyl methacrylate obtained in the above-mentioned Synthesis Example (I-43) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-233) The above-mentioned Example (I-2) except that the manyl methacrylate obtained in the above-mentioned Synthesis Example (I-43) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed, and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-234) The above-mentioned Example (I-3) except that the manyl methacrylate obtained in the above-mentioned Synthesis Example (I-43) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-44) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-43) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that manyl methacrylate was used instead of citronellyl methacrylate, and the obtained copolymer was used in the same manner. Of cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-235) to (Example I)
-242), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-44) was synthesized, and its characteristics were examined. (Example I-235) to (Example I-238) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-44) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 47 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0484]

[Table 47] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-239) to (Example I-242) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-44) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 48 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0486]

[Table 48] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-45) A hinokyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of hinokiol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-45) Polyhinokyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that hinokyl methacrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (19
(3 nm), the transparency was similarly examined, and it was found that the transmittance of polyhinokyl methacrylate was 45 in terms of 1 μm.
%Met.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyhinokyl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-243) to (Example I)
-245), each of the copolymers containing the hinokyl methacrylate obtained in Synthesis Example (I-45) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-243) The above-mentioned Example (I-) is used except that the hinokyl methacrylate obtained in the above-mentioned Synthesis Example (I-45) is used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that of Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-244) The above-mentioned Example (I-) is used except that the hinokyl methacrylate obtained in the above-mentioned Synthesis Example (I-45) is used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-245) The above-mentioned example (I- except that the hinokyl methacrylate obtained in the above-mentioned synthesis example (I-45) is used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-46) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-45) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that hinokyl methacrylate was used instead of citronellyl methacrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Furthermore, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-246) to (Example I)
253), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-46) was synthesized, and its characteristics were examined. (Example I-246) to (Example I-249) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-46) is used. Except for the above, a chemically amplified resist solution was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and this was used to form a pattern in the same manner as described above. Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 49 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0500]

[Table 49] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-250) to (Example I-253) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-46) is used. Except for the above, a chemically amplified resist solution was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), and this was used to form a pattern in the same manner as described above. Examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 50 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0502]

[Table 50] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-47) Ferguinyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of ferguinol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-47) Other than using ferginyl methacrylate,
Polyferginyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) described above, and this was used as the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polyferginyl methacrylate was 45% in terms of 1 μm.

Furthermore, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyferginyl methacrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-254) to (Example I)
-256), each of the copolymers containing ferguinyl methacrylate obtained in Synthesis Example (I-47) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-254) The above-mentioned Example (I) was repeated except that the ferruginyl methacrylate obtained in the above-mentioned Synthesis Example (I-47) was used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in -1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-255) The above-mentioned Example (I) was repeated except that the ferruginyl methacrylate obtained in the above-mentioned Synthesis Example (I-47) was used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in -2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-256) The above-mentioned Example (I) was repeated except that the ferruginyl methacrylate obtained in the above-mentioned Synthesis Example (I-47) was used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in -3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a 0.5 μm positive line and space pattern could be resolved. (Synthesis Example I-48) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-47) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer obtained by synthesizing a copolymer in the same manner as in the above Synthesis Example (I-2) except that filginyl methacrylate was used instead of citronellyl methacrylate. Was used as a similar cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Furthermore, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-257) to (Example I)
-264), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-48) was synthesized, and its characteristics were examined. (Example I-257) to (Example I-260) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-48) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 51 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0516]

[Table 51] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-261) to (Example I-264) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-48) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 52 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0518]

[Table 52] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-49) Totaryl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of totarol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-49) Polytotalyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that totalyl methacrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (19
(3 nm), the transparency was similarly examined, and it was found that the transmittance of polytotaryl methacrylate was 1 μm and was 45.
%Met.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polytotaryl methacrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-265) to (Example I)
-267), the copolymers containing totaryl methacrylate obtained in Synthesis Example (I-49) were synthesized, and photosensitive materials containing the same were obtained, and their properties were examined. (Example I-265) In place of the citronellyl methacrylate, the above-mentioned example (I-) is used except that the totaryl methacrylate obtained in the above-mentioned synthesis example (I-49) is used.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied on a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-266) In place of the citronellyl methacrylate, the above-mentioned example (I-) is used except that the totaryl methacrylate obtained in the above-mentioned synthesis example (I-49) is used.
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-267) The above-mentioned Example (I-) was used except that the totaryl methacrylate obtained in the above-mentioned Synthesis Example (I-49) was used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-50) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-49) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-2) above except that totaryl methacrylate was used instead of citronellyl methacrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-268) to (Example I)
-275), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-50) was synthesized, and its characteristics were examined. (Example I-268) to (Example I-271) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-50) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 53 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0532]

[Table 53] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-272) to (Example I-275) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-50) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 54 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0534]

[Table 54] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-51) A sugyl methacrylate was obtained in the same manner as in the above Synthesis Example (I-1) except that citronellol was replaced with the same amount of sugiol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-51) Polysgyl methacrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that sugyl methacrylate was used. A cyclohexanone solution similar to the above was used. ArF excimer laser light (193n
When the transparency to m) was examined in the same manner, the transmittance of polysugyl methacrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate by carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polysugyl methacrylate was 0.3 when the etching rate of PMMA was 1. .

Hereinafter, (Example I-276) to (Example I)
-278), each of the copolymers containing sugyl methacrylate obtained in Synthesis Example (I-51) was synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-276) The above-mentioned Example (I-1) except that the sugyl methacrylate obtained in the above-mentioned Synthesis Example (I-51) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-277) The above-mentioned Example (I-2) except that the sugyl methacrylate obtained in the above-mentioned Synthesis Example (I-51) is used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-278) The above-mentioned Example (I-3) except that the sugyl methacrylate obtained in the above-mentioned Synthesis Example (I-51) is used in place of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-52) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-51) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in the above Synthesis Example (I-2) except that sugyl methacrylate was used instead of citronellyl methacrylate, and the obtained copolymer was treated in the same manner. Of cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (198 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Furthermore, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-279) to (Example I)
-286), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-52) was synthesized, and its characteristics were investigated. (Example I-279) to (Example I-282) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-52) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern is formed in the same manner as described above using the solution, Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 55 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0548]

[Table 55] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Example I-283) to (Example I-286) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-52) is used. Other than the above, a chemically amplified resist solution is obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), a pattern is formed in the same manner as described above, and the characteristics thereof are Examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 56 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0550]

[Table 56] In each of the examples, a 0.15 μm line-and-space pattern could be obtained. (Synthesis Example I-53) 24 g of acrylic acid, 31 g of citronellol, and 15 g of paratoluenesulfonic acid were heated to reflux in 500 mL of toluene at an oil temperature of 150 ° C. for 19 hours. Then, the reaction was stopped with a saturated sodium hydrogen carbonate aqueous solution, and ether was added. The two layers were separated, the aqueous layer was extracted with ether, and the organic layers were combined and washed with a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium hydroxide solution to remove the acid. In addition, saturated ammonium chloride solution is used to p
H was adjusted to 7 and dried with saturated saline and anhydrous sodium sulphate. Finally, the obtained oily substance was distilled under reduced pressure to obtain citronellyl acrylate. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-53) Polycitronellyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-1) except that citronellyl acrylate was used. Was the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the 1-μm conversion transmittance of polycitronellyl acrylate was 45%.

Furthermore, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polycitronellyl acrylate was 0.
It was 3.

Hereinafter, (Example I-287) to (Example I)
-289), each of the copolymers containing citronellyl acrylate obtained in Synthesis Example (I-531) was synthesized, and a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-287) The above-mentioned Example (I-) was used except that the citronellyl acrylate obtained in the above-mentioned Synthesis Example (I-53) was used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 1).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-1), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-288) In place of the citronellyl methacrylate, the citronellyl acrylate obtained in the above-mentioned synthesis example (I-53) is used, but in the above-mentioned example (I-).
A copolymer was synthesized in the same manner as 2).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-2), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-289) The above-mentioned Example (I-) is used except that the citronellyl acrylate obtained in the above-mentioned Synthesis Example (I-53) is used instead of the citronellyl methacrylate.
A copolymer was synthesized in the same manner as 3).

The obtained copolymer was applied onto a silicon wafer as a solution similar to that in Example (I-3), and then prebaked, exposed and developed under the same conditions to form a pattern. The characteristics were investigated.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-54) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-53) was synthesized, and the copolymer was evaluated.

Specifically, except that citronellyl acrylate is used in place of citronellyl methacrylate,
A copolymer was synthesized in the same manner as in Synthesis Example (I-2) above, and the obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, when the etching rate with carbon tetrafluoride gas (CF ₄ ) gas was compared with PMMA under the same conditions as in Synthesis Example (I-2) above,
When the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-290) to (Example I)
-297), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-54) was synthesized, and its characteristics were examined. (Example I-290) to (Example I-293) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-54) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 57 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0564]

[Table 57] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-294) to (Example I-297) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-54) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and a pattern was formed in the same manner as above, and its characteristics were examined. .

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 58 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0566]

[Table 58] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example I-55) The above-mentioned Synthesis Example (I-5) except that citronellol was replaced with the same amount of pinocampheol.
Pinocamphyl acrylate was obtained in the same manner as 3). (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-55) Other than using pinocamphyl acrylate,
Polypinocamphyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above, and this was used as the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polypinocanphy acrylate in terms of 1 μm was 45%.

Furthermore, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polypinocamphyl acrylate is 0.3 when the etching rate of PMMA is 1. there were.

Hereinafter, (Example I-298) to (Example I)
-300), each of the copolymers containing the pinocamphyl acrylate obtained in Synthesis Example (I-55) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-298) In place of the citronellyl acrylate, the above-mentioned Example (I- except that the pinocamphyl acrylate obtained in the above-mentioned Synthesis Example (I-55) is used.
A copolymer was synthesized in the same manner as 287).

The resulting copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-299) In place of the citronellyl acrylate, the pinocamphyl acrylate obtained in the above-mentioned synthesis example (I-55) is used, but the above-mentioned example (I-) is used.
288) and a copolymer was synthesized.

The resulting copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-300) The above-mentioned example (I-300) was used except that the pincanfil acrylate obtained in the above-mentioned synthesis example (I-55) was used in place of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in 289).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-56) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-55) was synthesized, and the copolymer was evaluated.

Specifically, except that pinocamphyl acrylate is used instead of citronellyl acrylate,
A copolymer was synthesized in the same manner as in the above-mentioned Synthesis Example (I-54), and the obtained copolymer was used as the same cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-301) to (Example I)
-308), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-56) was synthesized, and its characteristics were examined. (Example I-301) to (Example I-304) The copolymer obtained in Synthesis Example (I-56) is used instead of the copolymer obtained in Synthesis Example (I-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 59 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0580]

[Table 59] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-305) to (Example I-308) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-56) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and a pattern was formed in the same manner as above, and its characteristics were examined. .

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 60 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0582]

[Table 60] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example I-57) Geranyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of geraniol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-57) Polygeranyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that geranyl acrylate was used. A cyclohexanone solution similar to the above was used. ArF excimer laser light (193
Similarly, the transparency to polygeranyl acrylate was 45%, which was 1 μm.

Furthermore, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polygeranyl acrylate was 0.3 when the etching rate of PMMA was 1. .

Hereinafter, (Example I-309) to (Example I)
-311), the copolymers containing geranyl acrylate obtained in Synthesis Example (I-57) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-309) The above-mentioned Example (I-28) is repeated except that the geranyl acrylate obtained in the above-mentioned Synthesis Example (I-57) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-310) The above-mentioned Example (I-28) is repeated except that the geranyl acrylate obtained in the above-mentioned Synthesis Example (I-57) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The resulting copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-311) The above-mentioned Example (I-28) is repeated except that the geranyl acrylate obtained in the above-mentioned Synthesis Example (I-57) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-58) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-57) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that geranyl acrylate was used instead of citronellyl acrylate, and the obtained copolymer was used in the same manner. Of cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-312) to (Example I)
-319), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-58) was synthesized, and its characteristics were investigated. (Example I-312) to (Example I-315) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-58) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 61 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0596]

[Table 61] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-316) to (Example I-319) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-58) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 62 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0598]

[Table 62] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-59) The above-mentioned Synthesis Example (I-5) except that citronellol was replaced with the same amount of fentyl alcohol.
Fentyl acrylate was obtained in the same manner as 3). (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-59) Polyphentyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above, except that fentyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (1
When the transparency to (93 nm) was similarly examined,
The transmittance of polyphentyl acrylate is 4 in terms of 1 μm.
It was 5%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyphentyl acrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-320) to (Example I)
-322), each of the copolymers containing fentyl acrylate obtained in Synthesis Example (I-59) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-320) The above-mentioned Example (I-28) is repeated except that the fentyl acrylate obtained in the above-mentioned Synthesis Example (I-59) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-321) The above-mentioned Example (I-28) is repeated except that the fentyl acrylate obtained in the above-mentioned Synthesis Example (I-59) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-322) The above-mentioned Example (I-28) is repeated except that the fentyl acrylate obtained in the above-mentioned Synthesis Example (I-59) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-60) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-59) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that fentyl acrylate was used instead of citronellyl acrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-323) to (Example I)
-330), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-60) was synthesized, and its characteristics were investigated. (Example I-323) to (Example I-326) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-60) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 63 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0612]

[Table 63] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-327) to (Example I-330) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-60) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 64 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0614]

[Table 64] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-61) Neryl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of nerol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-61) Polyneryl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) except that neryl acrylate was used. A cyclohexanone solution similar to the above was used. ArF excimer laser light (193n
Similarly, when the transparency to m) was examined, the transmittance of polyneryl acrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyneryl acrylate was 0.3 when the etching rate of PMMA was 1. .

Hereinafter, (Example I-331) to (Example I)
-333), each of the copolymers containing neryl acrylate obtained in Synthesis Example (I-61) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-331) The above-mentioned Example (I-287) is used except that the neryl acrylate obtained in the above-mentioned Synthesis Example (I-61) is used in place of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-332) The above-mentioned Example (I-288) is used except that the neryl acrylate obtained in the above-mentioned Synthesis Example (I-61) is used in place of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-333) The above-mentioned Example (I-289) is used except that the neryl acrylate obtained in the above-mentioned Synthesis Example (I-61) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-62) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-61) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above, except that neryl acrylate was used instead of citronellyl acrylate, and the obtained copolymer was used in the same manner. Of cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-334) to (Example I)
-341), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-62) was synthesized, and its characteristics were examined. (Example I-334) to (Example I-337) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-62) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 65 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0628]

[Table 65] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-338) to (Example I-341) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-62) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 66 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0630]

[Table 66] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-63) Bornyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of borneol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-63) Polybornyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that bornyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193
When the transparency to (nm) was examined in the same manner, the transmittance of polybornyl acrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polybornyl acrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-342) to (Example I)
-344), the copolymers containing bornyl acrylate obtained in the above Synthesis Example (I-63) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-342) The above-mentioned Example (I-28) is repeated except that the bornyl acrylate obtained in the above-mentioned Synthesis Example (I-63) is used in place of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-343) The above-mentioned Example (I-28) was carried out except that the bornyl acrylate obtained in the above-mentioned Synthesis Example (I-63) was used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-344) The above-mentioned Example (I-28) is repeated except that the bornyl acrylate obtained in the above-mentioned Synthesis Example (I-63) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-64) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-63) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that bornyl acrylate was used in place of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Furthermore, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-345) to (Example I)
-352), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-64) was synthesized, and its characteristics were examined. (Example I-345) to (Example I-348) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-64) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 67 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0644]

[Table 67] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-349) to (Samurai Historical Example I-352) The copolymer obtained in Synthetic Example (I-64) is used instead of the copolymer obtained in Synthetic Example (I-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 68 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0646]

[Table 68] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-65) Cineryl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of cinerol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-65) Polycineryl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that cineryl acrylate was used. The same cyclohexanone solution as described above was used. ArF excimer laser light (193
Similarly, the transparency of the polycineryl acrylate was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polycineryl acrylate was 0.3 when the etching rate of PMMA was 1. .

Hereinafter, (Example I-353) to (Example I)
-355), the copolymers containing cineryl acrylate obtained in Synthesis Example (I-65) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-353) The above-mentioned example (I-28) is repeated except that the cyneryl acrylate obtained in the above-mentioned synthesis example (I-65) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-354) The above-mentioned example (I-28) is used except that the cyneryl acrylate obtained in the above-mentioned synthesis example (I-65) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-355) The above-mentioned Example (I-28) is repeated except that the cyneryl acrylate obtained in the above-mentioned Synthesis Example (I-65) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm positive line and space pattern could be resolved. (Synthesis Example I-66) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-65) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that cyneryl acrylate was used in place of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied onto a quartz wafer in a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-356) to (Example I)
-363), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-66) was synthesized, and its characteristics were examined. (Example I-356) to (Example I-359) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-66) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 69 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0660]

[Table 69] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-360) to (Example I-363) The copolymer obtained in Synthesis Example (I-66) is used instead of the copolymer obtained in Synthesis Example (I-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 70 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0662]

[Table 70] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-67) A pinyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of pinol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-67) Polypinyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that pinyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193n
When the transparency to m) was examined in the same manner, the transmittance of polypinyl acrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate by carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polypinyl acrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-364) to (Example I)
-366), each of the copolymers containing pinyl acrylate obtained in Synthesis Example (I-67) was synthesized, and a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-364) The above-mentioned Example (I-287) is used except that the pinyl acrylate obtained in the above-mentioned Synthesis Example (I-67) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-365) The above-mentioned Example (I-288) is used except that the pinyl acrylate obtained in the above-mentioned Synthesis Example (I-67) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-366) The above-mentioned Example (I-289) is used except that the pinyl acrylate obtained in the above-mentioned Synthesis Example (I-67) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm positive line and space pattern could be resolved. (Synthesis Example I-68) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-67) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that pinyl acrylate was used in place of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-367) to (Example I)
-374), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-68) was synthesized and its characteristics were investigated. (Example I-367) to (Example I-370) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-68) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 71 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0676]

[Table 71] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-371) to (Example I-374) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-68) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 72 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0678]

[Table 72] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-69) Ascaridyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of ascaridol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-69) Polyascaridyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that ascaridyl acrylate was used. Was the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polyascalydyl acrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyascalydyl acrylate was 0.
It was 3.

Hereinafter, (Example I-375) to (Example I)
-377), each of the copolymers containing ascaridyl acrylate obtained in Synthesis Example (I-69) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-375) In place of the citronellyl acrylate, the above-mentioned Example (I-2) is used except that the ascaridyl acrylate obtained in the above-mentioned Synthesis Example (I-69) is used.
A copolymer was synthesized in the same manner as in 87).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-376) In place of the citronellyl acrylate, the above-mentioned Example (I-2) is used except that the ascaridyl acrylate obtained in the above-mentioned Synthesis Example (I-69) is used.
A copolymer was synthesized in the same manner as 88).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-377) In place of the citronellyl acrylate, the above-mentioned Example (I-2) is used except that the alkali dil acrylate obtained in the above-mentioned Synthesis Example (I-69) is used.
A copolymer was synthesized in the same manner as in 89).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-70) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-69) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above, except that ascaridyl acrylate was used in place of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Furthermore, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-378) to (Example I)
-385), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-70) was synthesized, and its characteristics were examined. (Example I-378) to (Example I-381) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-70) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 73 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0692]

[Table 73] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-382) to (Example I-385) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-70) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 74 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0694]

[Table 74] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-71) Farnesyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of farnesol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-71) Polyfarnesyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) except that farnesyl acrylate was used. A cyclohexanone solution similar to the above was used. When the transparency to ArF excimer laser light (193 nm) was similarly examined, the transmittance of polyfarnesyl acrylate in terms of 1 μm was 45%.

Further, the etching rate of carbon tetrafluoride (CF ₄ ) gas was measured under the same conditions as described above, and as a result, the etching rate of polyfarnesyl acrylate was 0.
It was 3.

Hereinafter, (Example I-386) to (Example I)
388), the copolymers containing ascaridyl acrylate obtained in Synthesis Example (I-71) were synthesized, and photosensitive materials containing the same were obtained, and their properties were examined. (Example I-386) In place of the citronellyl acrylate, the above-mentioned Example (I-2) is used except that the farnesyl acrylate obtained in the above-mentioned Synthesis Example (I-71) is used.
A copolymer was synthesized in the same manner as in 87).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-387) In place of the citronellyl acrylate, the above-mentioned Example (I-2) is used except that the farnesyl acrylate obtained in the above-mentioned Synthesis Example (I-71) is used.
A copolymer was synthesized in the same manner as 88).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-388) In place of the citronellyl acrylate, the above-mentioned Example (I-2) is used except that the farnesyl acrylate obtained in the above-mentioned Synthesis Example (I-71) is used.
A copolymer was synthesized in the same manner as in 89).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-72) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-71) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in the above Synthesis Example (I-54) except that farnesyl acrylate was used instead of citronellyl acrylate, and the obtained copolymer was treated in the same manner. Of cyclohexanone solution.

This solution was applied onto a quartz wafer in a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-389) to (Example I)
-396), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-72) was synthesized, and its characteristics were examined. (Example I-389) to (Example I-392) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-72) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 75 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0708]

[Table 75] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-393) to (Example I-396) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-72) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 76 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0710]

[Table 76] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-73) The above-mentioned Synthesis Example (I-5) except that citronellol was replaced with the same amount of patchuryl alcohol.
Patchuryl acrylate was obtained in the same manner as 3). (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-73) Polypatchuryl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that patchoulyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (1
When the transparency to (93 nm) was similarly examined,
The transmittance of 1 μm of polypatryl acrylate is 4
It was 5%.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polypaturyl acrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-397) to (Example I)
-399), each of the copolymers containing patchoulyl acrylate obtained in Synthesis Example (I-73) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-397) The above-mentioned Example (I-28) is repeated except that the patchuryl acrylate obtained in the above-mentioned Synthesis Example (I-73) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-398) The above-mentioned Example (I-28) is repeated except that the patchuryl acrylate obtained in the above-mentioned Synthesis Example (I-73) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-399) In place of the citronellyl acrylate, the patchuryl acrylate obtained in the above Synthesis Example (I-73) is used, but in the above Example (I-28).
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-74) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-73) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that patchuryl acrylate was used instead of citronellyl acrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-400) to (Example I)
-407), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-74) was synthesized, and its characteristics were examined. (Example I-400) to (Example I-403) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-74) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 77 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0724]

[Table 77] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-404) to (Example I-407) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-74) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The results obtained are summarized in Table 78 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0726]

[Table 78] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-75) Neroridyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of nerolidol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-75) Polynerolidyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that nerolidyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (1
When the transparency to (93 nm) was similarly examined,
The transmittance of polynerolidyl acrylate in terms of 1 μm is 4
It was 5%.

Further, as a result of measuring the etching rate by the carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polynerolidyl acrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-408) to (Example I)
-410), each of the copolymers containing nerolidyl acrylate obtained in Synthesis Example (I-75) was synthesized, a photosensitive material containing the copolymer was obtained, and the characteristics thereof were examined. (Example I-408) The above-mentioned Example (I-28) is repeated except that the nerolidyl acrylate obtained in the above-mentioned Synthesis Example (I-75) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-409) The above-mentioned Example (I-28) is repeated except that the nerolidyl acrylate obtained in the above-mentioned Synthesis Example (I-75) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-410) The above-mentioned Example (I-28) is repeated except that the nerolidyl acrylate obtained in the above-mentioned Synthesis Example (I-75) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-76) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-75) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that nerolidyl acrylate was used instead of citronellyl acrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-411) to (Example I)
-418), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-76) was synthesized, and its characteristics were examined. (Example I-411) to (Example I-414) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-76) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 79 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0740]

[Table 79] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-415) to (Example I-418) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-76) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 80 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0742]

[Table 80] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-77) Carotyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of caroteol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-77) Polycarotyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that carotyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193
Similarly, when the transparency to (nm) was examined, the transmittance of polycarotyl acrylate in terms of 1 μm was 45%.

Furthermore, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polycarotyl acrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-419) to (Example I)
-421), the copolymers containing carotyl acrylate obtained in Synthesis Example (I-77) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-419) In place of the citronellyl acrylate, the above-mentioned Example (I-28) is used except that the carotyl acrylate obtained in the above-mentioned Synthesis Example (I-77) is used.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm negative line and space pattern could be resolved. (Example I-420) In place of the citronellyl acrylate, the carotyl acrylate obtained in the above Synthesis Example (I-77) is used, but in the above Example (I-28).
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-421) The above-mentioned example (I-28) is repeated except that the carotyl acrylate obtained in the above-mentioned synthesis example (I-77) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The copolymer thus obtained was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-78) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-77) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in the above-mentioned Synthesis Example (I-54) except that carotyl acrylate was used in place of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied onto a quartz wafer in a thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ )
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-422) to (Example I)
-429), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-78) was synthesized, and its characteristics were examined. (Example I-422) to (Example 425) Except that the copolymer obtained in Synthesis Example (I-78) is used instead of the copolymer obtained in Synthesis Example (I-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 81 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0756]

[Table 81] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-426) to (Example I-429) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-78) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 82 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0758]

[Table 82] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-79) A cazinyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of casino. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-79) Polycadinyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that cazinyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193
When the transparency to (nm) was examined in the same manner, the transmittance of the polycazinyl acrylate in terms of 1 μm was 45%.

Furthermore, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as above, the etching rate of polycazinyl acrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-430) to (Example I)
-432), the copolymers containing the cazinyl acrylate obtained in Synthesis Example (I-79) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-430) In place of the citronellyl acrylate, the above-mentioned example (I-28) is used except that the cazinyl acrylate obtained in the above-mentioned synthesis example (I-79) is used.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-431) In place of the citronellyl acrylate, the above-mentioned example (I-28) is used except that the cazinyl acrylate obtained in the above-mentioned synthesis example (I-79) is used.
A copolymer was synthesized in the same manner as 8).

The copolymer obtained was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-432) The above-mentioned Example (I-28) is repeated except that the cazinyl acrylate obtained in the above-mentioned Synthesis Example (I-79) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-80) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-79) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that cazinyl acrylate was used instead of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied onto a quartz wafer in a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-433) to (Example I)
-440), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-80) was synthesized, and its characteristics were examined. (Example I-433) to (Example I-436) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-80) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 83 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0772]

[Table 83] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-437) to (Example I-440) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-80) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 84 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0774]

[Table 84] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-81) Lancil acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of lanseol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-81) Polylansyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that lanyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193
When the transparency to (nm) was examined in the same manner, the transmittance of 1 μm of polylansyl acrylate was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polylansyl acrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-441) to (Example I)
-443), the copolymers containing lanyl acrylate obtained in Synthesis Example (I-81) above were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-441) In place of the citronellyl acrylate, the above-mentioned example (I-28) is used except that the lanyl acrylate obtained in the above-mentioned synthesis example (I-81) is used.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-442) The above-mentioned Example (I-28) is repeated except that the lanyl acrylate obtained in the above-mentioned Synthesis Example (I-81) is used in place of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-443) In place of the citronellyl acrylate, the above-mentioned example (I-28) is used except that the lanyl acrylate obtained in the above-mentioned synthesis example (I-81) is used.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-82) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-81) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in the above Synthesis Example (I-54) except that lansyl acrylate was used instead of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-444) to (Example I)
-451), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-82) was synthesized, and its characteristics were examined. (Example I-444) to (Example I-447) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-82) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 85 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0788]

[Table 85] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-448) to (Example I-451) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-82) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 86 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0790]

[Table 86] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-83) Oydesmil acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of eudesmol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-83) Polyeudesmil acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that eudesmil acrylate was used. Was the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polyoidesyl acrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyeudesmil acrylate was 0.
It was 3.

Hereinafter, (Example I-452) to (Example I)
-454), each of the copolymers containing eudesmil acrylate obtained in Synthesis Example (I-83) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-452) In place of the citronellyl acrylate, the above-mentioned example (I-2) is used except that the eudesmil acrylate obtained in the above-mentioned synthesis example (I-83) is used.
A copolymer was synthesized in the same manner as in 87).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-453) In place of the citronellyl acrylate, the above-mentioned example (I-2) is used except that the eudesmil acrylate obtained in the above-mentioned synthesis example (I-83) is used.
A copolymer was synthesized in the same manner as 88).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-454) In place of the citronellyl acrylate, the above-mentioned example (I-2) is used except that the eudesmil acrylate obtained in the above-mentioned synthesis example (I-83) is used.
A copolymer was synthesized in the same manner as in 89).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-84) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-83) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that eudesmil acrylate was used instead of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied onto a quartz wafer in a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-455) to (Example I)
-462), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-84) was synthesized, and its characteristics were investigated. (Example I-455) to (Example I-458) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-84) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 87 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0804]

[Table 87] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-459) to (Example I-462) The copolymer obtained in Synthesis Example (I-84) is used instead of the copolymer obtained in Synthesis Example (I-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 88 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0806]

[Table 88] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-85) A ceryl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of sedrol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-85) Polycedryl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above, except that ceryl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193
When the transparency for (nm) was examined in the same manner, the transmittance of polycedryl acrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polycedryl acrylate is 0.3 when the etching rate of PMMA is 1. It was

[0808] Hereinafter, (Example I-463) to (Example I)
-465), the copolymers containing the ceryl acrylate obtained in the above Synthesis Example (I-85) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-463) The above-mentioned example (I-28) is repeated except that the cedolyl acrylate obtained in the above-mentioned synthesis example (I-85) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. Example I-464 The above example (I-28) is repeated except that the cedolyl acrylate obtained in the above synthesis example (I-85) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-465) The above-mentioned Example (I-28) is used except that the cedolyl acrylate obtained in the above-mentioned Synthesis Example (I-85) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-86) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-85) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in the above-mentioned Synthesis Example (I-54), except that cedolyl acrylate was used in place of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-466) to (Example I)
-473), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-86) was synthesized, and its characteristics were examined. (Example I-466) to (Example I-469) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-86) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 89 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0820]

[Table 89] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-470) to (Example I-473) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-86) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The results obtained are summarized in Table 90 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0822]

[Table 90] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-87) A guayyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of guayol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-87) Polyguayl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that guayl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193
When the transparency to (nm) was examined in the same manner, the transmittance of 1 μm of polyguayl acrylate was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyguayl acrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-474) to (Example I)
-476), each of the copolymers containing guayyl acrylate obtained in the above Synthesis Example (I-87) was synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-474) The above-mentioned Example (I-28) is used except that the guayyl acrylate obtained in the above-mentioned Synthesis Example (I-87) is used in place of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-475) In place of the citronellyl acrylate, the guayle acrylate obtained in the above synthesis example (I-87) is used, but the above-mentioned example (I-28) is used.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-476) In place of the citronellyl acrylate, the guayle acrylate obtained in the above Synthesis Example (I-87) is used, and the above-mentioned Example (I-28) is used.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm positive line and space pattern could be resolved. (Synthesis Example I-88) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-87) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that guayyl acrylate was used in place of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-477) to (Example I)
-484), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-88) was synthesized, and its characteristics were investigated. (Example I-477) to (Example I-480) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-88) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 91 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0836]

[Table 91] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-481) to (Example I-484) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-88) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 92 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0838]

[Table 92] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis example I-89) The above-mentioned synthesis example (I-53) except that citronellol was replaced by the same amount of kessoglycol.
In the same manner as in (1) to (2), a kessos glycosyl acrylate was obtained. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-89) A polykessoglycosyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above, except that the sessoglycosyl acrylate was used. This was used as the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, it was found that
The transmittance in terms of μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of the polykessoglycosyl acrylate is 0.3 when the etching rate of PMMA is 1. there were.

Hereinafter, (Example I-485) to (Example I)
-487), each of the copolymers containing the sessoglycosyl acrylate obtained in Synthesis Example (I-89) was synthesized, and a photosensitive material containing the copolymer was obtained, and its properties were investigated. (Example I-485) In place of the citronellyl acrylate, the above-mentioned example (I- except that the kesoglycosyl acrylate obtained in the above-mentioned synthesis example (I-89) is used.
A copolymer was synthesized in the same manner as 287).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, it was possible to resolve a negative line and space pattern of 0.5 μm. (Example I-486) The above-mentioned Example (I) was performed except that the kessosglycosyl acrylate obtained in the above-mentioned Synthesis Example (I-89) was used instead of the citronellyl acrylate.
-288) and a copolymer was synthesized.

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-487) The above-mentioned Example (I) was performed except that the kessosglycosyl acrylate obtained in the above-mentioned Synthesis Example (I-89) was used in place of the citronellyl acrylate.
-289) and a copolymer was synthesized.

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-90) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-89) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer obtained by synthesizing a copolymer in the same manner as in the above-mentioned Synthesis Example (I-54) except that a kessosglycosyl acrylate was used in place of the citronellyl acrylate was obtained. Was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-488) to (Example I)
-495), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-90) was synthesized, and its characteristics were investigated. (Example I-488) to (Example I-491) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-90) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 93 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0852]

[Table 93] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-492) to (Example I-495) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-90) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 94 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0854]

[Table 94] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-91) Phytyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of phytol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-91) Polyphytyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that phytyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193
When the transparency to (nm) was examined in the same manner, the transmittance of the polyphytyl acrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyphytyl acrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-496) to (Example I)
-498), the phytyl acrylate-containing copolymers obtained in Synthesis Example (I-91) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-496) The above-mentioned Example (I-28) is repeated except that the phytyl acrylate obtained in the above-mentioned Synthesis Example (I-91) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-497) The above-mentioned Example (I-28) is repeated except that the phytyl acrylate obtained in the above-mentioned Synthesis Example (I-91) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-498) The above Example (I-28) is repeated except that the phytyl acrylate obtained in the above Synthesis Example (I-91) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-92) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-91) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that phytyl acrylate was used instead of citronellyl acrylate, and the obtained copolymer was The same cyclohexanone solution was used.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-499) to (Example I)
-506), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-92) was synthesized, and its characteristics were examined. (Example I-499) to (Example I-502) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-92) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 95 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0868]

[Table 95] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-503) to (Example I-506) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-92) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 96 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0870]

[Table 96] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-93) Sucralyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of sclareol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-93) Polysclaryl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that sclaryl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (1
When the transparency to (93 nm) was similarly examined,
The transmittance of polysquaryl acrylate in terms of 1 μm is 4
It was 5%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polysclaryl acrylate is 0.3 when the etching rate of PMMA is 1.
Met.

Hereinafter, (Example I-507) to (Example I)
-509), each of the copolymers containing sucralyl acrylate obtained in Synthesis Example (I-93) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-507) In place of the citronellyl acrylate, the sucralyl acrylate obtained in the above synthesis example (I-93) is used, but in the above-mentioned example (I-28).
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-508) In place of the citronellyl acrylate, the sucralyl acrylate obtained in the above Synthesis Example (I-93) is used, but in the above Example (I-28).
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-509) In place of the citronellyl acrylate, the sucralyl acrylate obtained in the above synthesis example (I-93) is used, but in the above example (I-28).
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-94) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-93) was synthesized and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that sucralyl acrylate was used instead of citronellyl acrylate,
The obtained copolymer was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and the PMM was
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-510) to (Example I)
-517), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-94) was synthesized, and its characteristics were investigated. (Example I-510) to (Example I-513) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-94) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The results obtained are summarized in Table 97 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0884]

[Table 97] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-514) to (Example I-517) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-94) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 98 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0886]

[Table 98] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-95) Manyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of manol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-95) A polymanyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that manyl acrylate was used. A cyclohexanone solution similar to the above was used. ArF excimer laser light (193n
When the transparency to m) was examined in the same manner, the transmittance of polymanyl acrylate in terms of 1 μm was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polymanyl acrylate was 0.3 when the etching rate of PMMA was 1. .

[Example 1-518] to (Example I)
-520), each of the copolymers containing the manyl acrylate obtained in Synthesis Example (I-95) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-518) In place of the citronellyl acrylate, the above-mentioned example (I-287) is used except that the manyl acrylate obtained in the above-mentioned synthesis example (I-95) is used.
A copolymer was synthesized in the same manner as in.

The copolymer thus obtained was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-519) The above-mentioned Example (I-288) is used except that the manyl acrylate obtained in the above-mentioned Synthesis Example (I-95) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-520) The above-mentioned Example (I-289) is used except that the manyl acrylate obtained in the above-mentioned Synthesis Example (I-95) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in.

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-96) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-95) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that manyl acrylate was used instead of citronellyl acrylate, and the obtained copolymer was treated in the same manner. Of cyclohexanone solution.

This solution was applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (198 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-521) to (Example I)
-528), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-96) was synthesized, and its characteristics were examined. (Example I-521) to (Example I-524) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-96) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 99 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0900]

[Table 99] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-525) to (Example I-528) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-96) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 100 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0902]

[Table 100] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-97) A hinokyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of hinokiol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-97) Polyhinokyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that hinokyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (193
When the transparency for (nm) was examined in the same manner, the transmittance of 1 μm of polyhinokyl acrylate was 45%.

Further, as a result of measuring the etching rate by carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyhinokyl acrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-529) to (Example I)
-531), the copolymers containing the hinokyl acrylate obtained in Synthesis Example (I-97) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-529) The above-mentioned Example (I-28) is repeated except that the hinokyl acrylate obtained in the above-mentioned Synthesis Example (I-97) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-530) The above-mentioned Example (I-28) is repeated except that the hinokyl acrylate obtained in the above-mentioned Synthesis Example (I-97) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-531) The above-mentioned Example (I-28) is repeated except that the hinokyl acrylate obtained in the above-mentioned Synthesis Example (I-97) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-98) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-97) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above, except that hinokyl acrylate was used instead of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-532) to (Example I)
-539), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-98) was synthesized, and its characteristics were investigated. (Example I-532) to (Example I-535) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-98) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7) except for the above, and using this, the pattern formation was performed in the same manner as described above, and the characteristics thereof were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 101 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0916]

[Table 101] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-536) to (Example I-539) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-98) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11) except for the above, and using this, pattern formation was performed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 102 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[0918]

[Table 102] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-99) Ferguinyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of ferguinol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-99) Polyferginyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above, except that ferruginyl acrylate was used. This was used as the same cyclohexanone solution as described above. When the transparency to ArF excimer laser light (193 nm) was examined in the same manner, the transmittance of polyferginyl acrylate in terms of 1 μm was 45%.

Furthermore, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polyferginyl acrylate was 0.
It was 3.

[0921] Hereinafter, (Example I-540) to (Example I)
-542), each of the copolymers containing ferguinyl acrylate obtained in Synthesis Example (I-99) was synthesized, a photosensitive material containing the same was obtained, and the characteristics thereof were examined. (Example I-540) In place of the citronellyl acrylate, the ferguinyl acrylate obtained in the above Synthesis Example (I-99) is used, but in the above Example (I-2).
A copolymer was synthesized in the same manner as in 87).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-541) In place of the citronellyl acrylate, the ferguinyl acrylate obtained in the above Synthesis Example (I-99) is used, but in the above Example (I-2).
A copolymer was synthesized in the same manner as 88).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-542) The above-mentioned Example (I-2) is used except that the ferguinyl acrylate obtained in the above-mentioned Synthesis Example (I-99) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as in 89).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-100) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-99) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that ferginyl acrylate was used instead of citronellyl acrylate, and the obtained copolymer was obtained. Was used as a similar cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-543) to (Example I)
-550), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-100) was synthesized, and its characteristics were examined. (Example I-543) to (Example I-546) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-100) is used. except,
The chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and the pattern formation was performed using the same, and the characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 103 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0932]

[Table 103] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-547) to (Example I-550) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-100) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), and a pattern was formed in the same manner as described above, and its characteristics were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 104 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0934]

[Table 104] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-101) Totaryl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of totarol. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example I-101) Polytotaryl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that totalyl acrylate was used. Was the same cyclohexanone solution as described above. ArF excimer laser light (19
(3 nm), the transmittance of polytotaryl acrylate was 45% at 1 μm.
Met.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polytotaryl acrylate is 0.3 when the etching rate of PMMA is 1. It was

Hereinafter, (Example I-551) to (Example I)
-553), the copolymers containing totharyl acrylate obtained in Synthesis Example (I-101) were synthesized, and photosensitive materials containing the same were obtained, and their properties were examined. (Example I-551) In place of the citronellyl acrylate, the above-mentioned example (I-28) is used except that the totaryl acrylate obtained in the above-mentioned synthesis example (I-101) is used.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-552) In place of the citronellyl acrylate, the above-mentioned example (I-28) is used except that the totaryl acrylate obtained in the above-mentioned synthesis example (I-101) is used.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-553) The above Example (I-28) is used except that the totaryl acrylate obtained in the above Synthesis Example (I-101) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-102) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-101) was synthesized and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above, except that totaryl acrylate was used in place of citronellyl acrylate, and the obtained copolymer was obtained. The same cyclohexanone solution was used.

This solution was applied onto a quartz wafer in a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-554) to (Example I)
-561), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-102) was synthesized, and its characteristics were examined. (Example I-554) to (Example I-557) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-102) is used. except,
The chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and the pattern formation was performed using the same, and the characteristics were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 105 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0948]

[Table 105] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-558) to (Example I-561) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-102) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), and a pattern was formed in the same manner as described above, and its characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 106 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0950]

[Table 106] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-103) A sugyl acrylate was obtained in the same manner as in the above Synthesis Example (I-53) except that citronellol was replaced with the same amount of sugiol. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example I-103) Polysgyl acrylate was obtained in the same manner as in the case of the monomer of Synthesis Example (I-53) described above except that sugyl acrylate was used. A cyclohexanone solution similar to the above was used. ArF excimer laser light (193n
When the transparency to m) was examined in the same manner, the transmittance of 1 μm of polysugyl acrylate was 45%.

Further, as a result of measuring the etching rate with carbon tetrafluoride (CF ₄ ) gas under the same conditions as described above, the etching rate of polysgyl acrylate was 0.3 when the etching rate of PMMA was 1. .

[0952] Hereinafter, (Example I-562) to (Example I)
-564), the copolymers containing sugyl acrylate obtained in the above Synthesis Example (I-103) were respectively synthesized,
A photosensitive material containing this was obtained and its characteristics were investigated. (Example I-562) In place of the citronellyl acrylate, the sugyl acrylate obtained in the above synthesis example (I-103) is used, but the above-mentioned example (I-28) is used.
A copolymer was synthesized in the same manner as 7).

The obtained copolymer was used in Example (I-287).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-563) The above-mentioned Example (I-28) is repeated except that the sugyl acrylate obtained in the above-mentioned Synthesis Example (I-103) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 8).

The obtained copolymer was used in Example (I-288).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example I-564) The above-mentioned Example (I-28) is repeated except that the sugyl acrylate obtained in the above-mentioned Synthesis Example (I-103) is used instead of the citronellyl acrylate.
A copolymer was synthesized in the same manner as 9).

The obtained copolymer was used in Example (I-289).
After coating on a silicon wafer as a solution similar to,
Prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a positive line and space pattern of 0.5 μm could be resolved. (Synthesis Example I-104) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (I-103) was synthesized, and the copolymer was evaluated.

Specifically, a copolymer was synthesized in the same manner as in Synthesis Example (I-54) above except that sugyl acrylate was used in place of citronellyl acrylate, and the obtained copolymer was treated in the same manner. Of cyclohexanone solution.

This solution was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. As a result, the transmittance was 74%, and PMM was found.
It was better than A.

Further, under the same conditions as in Synthesis Example (I-54) above, carbon tetrafluoride gas (CF ₄ ) was used.
When the etching rate by gas was compared with that of PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

The following (Example I-565) to (Example I)
-572), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (I-104) was synthesized, and its characteristics were examined. (Example I-565) to (Example I-568) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-104) is used. except,
The chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-4) to (I-7), and the pattern formation was performed using the same, and the characteristics were examined.

Furthermore, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 107 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0964]

[Table 107] In each of the examples, a line and space of 0.15 μm could be resolved. (Example I-569) to (Example I-572) Instead of the copolymer obtained in Synthesis Example (I-2), the copolymer obtained in Synthesis Example (I-104) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (I-8) to (I-11), and a pattern was formed in the same manner as described above, and its characteristics were examined.

Further, in the same manner as in Synthesis Example (I-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 108 below together with the photoacid generator used. The etching rate is a value for PMMA.

[0966]

[Table 108] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example I-105) The 3,3-bis-4′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone used as the dissolution inhibitor in the above-mentioned Examples is as follows. Was synthesized. That is, 3,3
-Bis-4'-hydroxynaphthalenyl-1 (3H)-
Isobenzofuranone 5.4 g acetonitrile 300 m
L'is dissolved in 4'-dimethylaminopyridine.
3 mg was added. Then, a solution of 68 g of di-t-butylpyrocarbonate in 20 mL of acetonitrile was added dropwise, and the mixture was heated at room temperature for 1 hour. 600 mL of ethyl acetate
It was diluted with and washed with an aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution. Finally, it was dried over anhydrous sodium sulfate and recrystallized. Example II In this example, a base resin containing a compound having a menthyl group or a menthyl derivative group in its skeleton was synthesized, a photosensitive material was produced using this, and its evaluation was performed. In particular, the base resin was synthesized by variously changing the types of the above compounds and the copolymerization ratio. (Synthesis example II-1) Methacrylic acid 24 g, menthol 31
g, and 15 g of paratoluenesulfonic acid are added to toluene 5
The mixture was heated under reflux in 00 mL at an oil temperature of 150 ° C. for 19 hours. Then, the reaction was stopped with a saturated sodium hydrogen carbonate aqueous solution, and ether was added. The two layers were separated and the aqueous layer was extracted with ether, the organic layers were combined and then washed with saturated aqueous sodium hydrogen carbonate solution and aqueous sodium hydroxide solution to remove the acid. Further, the pH was adjusted to 7 with a saturated aqueous solution of ammonium chloride, and the solution was dried with saturated saline and anhydrous sodium sulfate. The finally obtained oily substance was distilled under reduced pressure to obtain menthyl methacrylate. (Evaluation of Homopolymer Composed of Monomer Obtained in Synthesis Example II-1) Menthyl methacrylate (2.1 g) and azoisobutyronitrile (0.4 g) as a polymerization initiator were dissolved in toluene (6 mL).

The obtained solution was frozen in liquid nitrogen, deaerated three times for 20 minutes and then brought to room temperature. Then, under a nitrogen stream, the oil temperature was heated at 70 ° C for 16 hours to obtain 600 m of methanol
The reaction was stopped by L. After reprecipitation with methanol, it was filtered off and the solvent was distilled off under vacuum to obtain polymenthyl methacrylate.

This was made into a cyclohexanone solution, which was then applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined.

Further, carbon tetrafluoride (CH
₄ ) The etching rate by gas was measured. The dry etching resistance was evaluated under the following conditions. That is, the flow rate of (CH ₄ ) was 12.6 sccm, the degree of vacuum was 10 mtorr, and the microwave output was 150 W.

Also, instead of polymenthyl methacrylate, novolac resin and polymethyl methacrylate were each made into a cyclohexanone solution, and a comparative example (II
-1) and Comparative Example (II-2).

The obtained solutions of Comparative Example (II-1) and Comparative Example (II-2) were coated on a quartz wafer in the same manner as above to prepare A.
The transparency to rF excimer laser light was examined. Further, the etching rate with carbon tetrafluoride gas was examined under the same conditions. The results obtained are shown in Table 10 below.
Summarize in 9.

The etching rate of polymenthyl methacrylate was 0.3 when the etching rate of PMMA was 1.

[0973]

[Table 109] As shown in Table 109, the polymer having a terpenoid skeleton has a high transmittance at 193 nm and an excellent dry etching property. On the other hand, it can be seen that novolac resin has a remarkably low transmittance and PMMA has poor etching resistance.

Hereinafter, in Examples (II-1) to (II-3), the copolymers containing menthyl methacrylate obtained in the above Synthesis Example (II-1) were synthesized, respectively, and the photosensitizers containing them were synthesized. The material was obtained and its properties were investigated.

(Example II-1) 9 g of menthyl methacrylate, 1 g of glycidyl methacrylate, and 0.5 g of azoisobutyronitrile as a polymerization initiator were dissolved in 30 mL of toluene.

The obtained solution was frozen in liquid nitrogen, deaerated three times for 20 minutes, and then brought to room temperature. Next, under a nitrogen stream, the oil was heated at 70 ° C. for 16 hours, and the reaction was stopped with methanol. After reprecipitation with methanol, the mixture was filtered off and the solvent was distilled off under vacuum to obtain a target copolymer.

1 g of the obtained copolymer was dissolved in 9 mL of methyl 3-methoxypropionate, and the solution was applied on a silicon wafer to a thickness of 1 μm, and then prebaked at 100 ° C. After that, electron beam exposure (exposure amount 10 μCc
m ⁻² , 20 keV) and then developed with methyl ethyl ketone to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. Example II-2 9 g of menthyl methacrylate, 1 g of allyl methacrylate, and 0.5 g of azoisobutyronitrile as a polymerization initiator were dissolved in 30 mL of toluene. The resulting solution was frozen in liquid nitrogen, degassed 5 times for 20 minutes, and then brought to room temperature. Next, the mixture was heated at an oil temperature of 70 ° C for 16 hours under a nitrogen stream, and the reaction was stopped with methanol. After reprecipitation with methanol, the mixture was filtered off and the solvent was distilled off under vacuum to obtain the target copolymer.

The obtained copolymer was prepared according to the above-mentioned Example (II-
After being coated on a silicon wafer as a solution similar to 1), prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example II-3) 5 g of menthyl methacrylate, 5 g of α-chlorotrifluoroethyl acrylate, and 0.5 g of azoisobutyronitrile as a polymerization initiator were dissolved in 28 mL of tetrahydrofuran (hereinafter abbreviated as THF).

The obtained solution was frozen in liquid nitrogen, degassed 5 times for 20 minutes, and then brought to room temperature. Then, the mixture was heated under a nitrogen stream at an oil temperature of 60 ° C. for 16 hours, and the reaction was stopped with hexane. After reprecipitation with hexane, the product was filtered off and the solvent was distilled off under vacuum to obtain a target copolymer.

The obtained copolymer was prepared according to the above-mentioned Example (II-
After coating on a silicon wafer as a solution similar to 1), prebaking and exposure were performed under the same conditions, and further development was performed using methyl isobutyl ketone to form a pattern, and its characteristics were examined.

As a result, a 0.5 μm positive line and space pattern could be resolved. (Synthesis Example II-2) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (II-1) was synthesized, and its characteristics were evaluated.

Menthyl methacrylate, t-butyl methacrylate and methacrylic acid (10 g) were prepared at a ratio of 50:30:20 and dissolved in 40 mL of THF together with 0.5 g of azoisobutyronitrile as a polymerization initiator.

The obtained solution was frozen in liquid nitrogen, deaerated 5 times for 20 minutes, and then brought to room temperature. Next, the mixture was heated at an oil temperature of 60 ° C. for 9 hours under a nitrogen stream, and the reaction was stopped with hexane. After reprecipitation with hexane, the mixture was filtered and the solvent was removed under vacuum to obtain the target copolymer.

The obtained copolymer was made into a cyclohexanone solution, which was coated on a quartz wafer to a film thickness of 1 μm, and then ArF
As a result of examining the transparency with respect to the excimer laser beam (193 nm), the transmittance was 74%, which was superior to PMMA.

Furthermore, as a result of comparing the etching rate with carbon tetrafluoride gas (CF ₄ ) gas with PMMA, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3.

[0988] The dry etching resistance was evaluated under the following conditions. That is, the flow rate of CF ₄ is 1
The pressure was 2.6 sccm, the degree of vacuum was 10 mtorr, and the microwave output was 150 W.

The following Examples (II-4) to (II-1)
In 1), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-2) was synthesized, and its characteristics were investigated. (Example II-4) 2 g of the copolymer obtained in Synthesis Example (II-2) and 0.04 g of triphenylsulfonium triflate as a photoacid generator were dissolved in 8 mL of 2-ethoxyethyl acetate.

This was applied on a silicon wafer to a film thickness of 0.8 μm, and then prebaked at 100 ° C. Then A
After exposure to rF excimer laser (40 mJcm ^-2 ), development was performed with an aqueous solution of tetramethylammonium hydroxide to form a pattern, and its characteristics were examined. as a result,
A line and space of 0.15 μm could be resolved.

Furthermore, in the same manner as in Synthesis Example (II-1),
When the transparency and the dry etching resistance were evaluated, the transmittance was 60% and the etching rate was 0.3, which was excellent with respect to PMMA. (Example II-5) to (Example II-7) A chemically amplified resist solution was prepared using the photo-acid generator shown in Table 110 below, and a silicon wafer was prepared in the same manner as in Example (II-4) above. After coating on the surface, prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined. In each example, the amount of the photo-acid generator added was 0.05 g.

Further, the transparency and the dry etching resistance were evaluated in the same manner as in Synthesis Example (II-1). The results are also shown in Table 110 below. The etching rate is PMM.
It is a value for A.

[0993]

[Table 110] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-8) 2 g of the copolymer obtained in Synthesis Example (II-2), 0.04 g of triphenylsulfonium triflate as a photoacid generator, and 3 as a dissolution inhibitor.
3-bis-4'-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone 0.1 g,
It was dissolved in 8 mL of 2-ethoxyethyl acetate.

This was applied on a silicon wafer to a film thickness of 0.8 μm, and then prebaked at 100 ° C. Then A
After exposure to rF excimer laser (40 mJcm ^-2 ), development was performed with an aqueous solution of tetramethylammonium hydroxide to form a pattern, and its characteristics were examined. as a result,
A line and space of 0.15 μm could be resolved.

Furthermore, in the same manner as in Synthesis Example (II-1),
When the transparency and the dry etching resistance were evaluated, the transmittance was 55%, and the etching rate was excellent with respect to PMMA of 0.3. (Example II-9) to (Example II-11) A chemically amplified resist solution was prepared using the photo-acid generator shown in Table 111 below, and a silicon wafer was prepared in the same manner as in Example (II-8) above. After coating on the surface, prebaking, exposure, and development were performed under the same conditions to form a pattern, and its characteristics were examined. In each example, the amount of the photo-acid generator added was 0.05 g.

Further, the transparency and the dry etching resistance were evaluated in the same manner as in Synthesis Example (II-1). The results are also shown in Table 111 below. The etching rate is PMM.
It is a value for A.

[0997]

[Table 111] In each of the examples, a line and space pattern of 0.15 μm could be obtained.

In this example, menthyl methacrylate (a monomer represented by the general formula (2)), t-butyl methacrylate (a functional group capable of decomposing with an acid), and methacrylic acid (an alkali-soluble group) are shown in FIG. Any composition ratio can be set within the hatched area. (Synthesis example II-3) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 50: 2.
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was set to 5:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-12) to Examples (II-
In 19), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-3) was synthesized, and its characteristics were examined. (Example II-12) to (Example II-15) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-3) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1001] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 112 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1002]

[Table 112] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-16) to (Example II-19) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-3) is used. , Except that the dissolution inhibitor was changed to 3,3-bis-3′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone, Examples (II-8) to Examples described above. (II-11)
A chemically amplified resist was obtained in the same manner as described above, a pattern was formed using the resist in the same manner as described above, and its characteristics were examined.

[1003] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 113 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1004]

[Table 113] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-4) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 50: 2.
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was 0:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1005] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1006] The following Examples (II-20) to Examples (II-
In 27), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-4) was synthesized and its characteristics were examined. (Example II-20) to (Example II-23) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-4) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1007] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 114 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1008]

[Table 114] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-24) to (Example II-27) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-4) was used. , Except that the dissolution inhibitor was changed to 3,3-bis-2′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone, the above-mentioned Examples (II-8) to Examples (II-11)
A chemically amplified resist was obtained in the same manner as above, and a pattern was formed using the same in the same manner as described above, and its characteristics were examined.

[1009] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 115 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1010]

[Table 115] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-5) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 45: 3.
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was set to 5:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1010] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1012] The following Examples (II-28) to (II-)
In 35), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-5) was synthesized, and its characteristics were investigated. (Example II-28) to (Example II-31) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-5) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1013] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 116 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1014]

[Table 116] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-32) to (Example II-35) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-5) is used. , Except that the dissolution inhibitor was changed to 3,3-bis-5′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone, the above-mentioned Examples (II-8) to Examples (II-11)
A chemically amplified resist was obtained in the same manner as above, and a pattern was formed using the same in the same manner as described above, and its characteristics were examined.

[1015] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 117 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1016]

[Table 117] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-6) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 45: 3.
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was 0:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1017] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1018] The following Examples (II-36) to Examples (II-
In 43), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-6) was synthesized, and its characteristics were investigated. (Example II-36) to (Example II-39) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-6) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1019] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 118 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1020]

[Table 118] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-40) to (Example II-43) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-6) is used. , Except that the dissolution inhibitor was changed to 3,3-bis-6′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone, the above-mentioned Examples (II-8) to Examples (II-11)
A chemically amplified resist was obtained in the same manner as above, and a pattern was formed using the same in the same manner as described above, and its characteristics were examined.

[1021] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 119 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1022]

[Table 119] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-7) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 45: 2.
A copolymer was obtained in the same manner as in Synthesis Example (II-2) above except that the ratio was 5:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1023] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1024] The following Examples (II-44) to Examples (II-
In 51), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-7) was synthesized, and its characteristics were examined. (Example II-44) to (Example II-47) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-7) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1025] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 120 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1026]

[Table 120] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-48) to (Example II-51) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-7) was used. , Except that the dissolution inhibitor was changed to 3,3-bis-7′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone, the above-mentioned Examples (II-8) to Examples (II-11)
A chemically amplified resist was obtained in the same manner as above, and a pattern was formed using the same in the same manner as described above, and its characteristics were examined.

[1027] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 121 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1028]

[Table 121] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-8) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 45: 2.
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was 0:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1029] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1030] The following Examples (II-52) to (II-)
In 59), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-8) was synthesized, and its characteristics were examined. (Example II-52) to (Example II-55) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-8) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1031] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 122 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1032]

[Table 122] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-56) to (Example II-59) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-8) is used. , Except that the dissolution inhibitor was changed to 3,3-bis-8′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone, the above-mentioned Examples (II-8) to Examples (II-11)
A chemically amplified resist was obtained in the same manner as above, and a pattern was formed using the same in the same manner as described above, and its characteristics were examined.

[1033] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 123 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1034]

[Table 123] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-9) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 40: 4.
A copolymer was obtained in the same manner as in Synthesis Example (II-2) above except that the ratio was 0:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1035] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1036] The following Examples (II-60) to Examples (II-
In 67), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-9) was synthesized, and its characteristics were examined. (Example II-60) to (Example II-63) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-9) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1037] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 124 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1038]

[Table 124] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-64) to (Example II-67) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-9) was used. , Except that the dissolution inhibitor was changed to 3,3-bis-1′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isononaphthalenofuranone. Example (II-1
A chemically amplified resist was obtained in the same manner as in 1), and using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

[1039] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 125 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1040]

[Table 125] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-10) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 40:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was set to 35:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1041] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1042] The following Examples (II-68) to Examples (II-
In 75), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-10) was synthesized, and its characteristics were investigated. (Example II-68) to (Example II-71) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-10) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1043] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 126 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1044]

[Table 126] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-72) to (Example II-75) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-10) was used. In Example (II-8) to Example described above, except that the dissolution inhibitor was changed to 3,3-bis-2′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isononaphthalenofuranone. Example (II-
A chemically amplified resist was obtained in the same manner as in 11), a pattern was formed in the same manner as described above, and the characteristics thereof were examined.

[1045] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 127 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1046]

[Table 127] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-11) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 40:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was 30:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1047] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1048] The following Examples (II-76) to Examples (II-
In 83), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-11) was synthesized, and its characteristics were examined. (Example II-76) to (Example II-79) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-11) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1049] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 128 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1050]

[Table 128] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-80) to (Example II-83) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-11) was used. , Except that the dissolution inhibitor was changed to 3,3-bis-3′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isononaphthalenofuranone. Example (II-
A chemically amplified resist was obtained in the same manner as in 11), a pattern was formed in the same manner as described above, and the characteristics thereof were examined.

[1051] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 129 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1052]

[Table 129] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-12) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 40:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was 25:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1053] Further, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1054] The following Examples (II-84) to Examples (II-
In 91), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-12) was synthesized, and its characteristics were examined. (Example II-84) to (Example II-87) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-12) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1055] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 130 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1056]

[Table 130] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-88) to (Example II-91) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-12) was used. , Except that the dissolution inhibitor was changed to 3,3-bis-4'-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isononaphthalenofuranone. Example (II-
A chemically amplified resist was obtained in the same manner as in 11), a pattern was formed in the same manner as described above, and the characteristics thereof were examined.

[1057] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 131 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1058]

[Table 131] In each of the examples, a line and space pattern of 0.15 μm could be obtained.

(Synthesis Example II-13) A copolymer was prepared in the same manner as in Synthesis Example (II-2) except that the ratio of menthyl methacrylate, t-butyl methacrylate and methacrylic acid was 40:20:40. To obtain a cyclohexanone solution similar to the above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1060] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1061] The following Examples (II-92) to Examples (II-
In 99), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-13) was synthesized, and its characteristics were examined. (Example II-92) to (Example II-95) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-13) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1062] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 132 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1063]

[Table 132] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-96) to (Example II-99) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-13) was used. In Example (II-8) to Example, except that the dissolution inhibitor was changed to 3,3-bis-5′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isonaphthalenofuranone. Example (II-
A chemically amplified resist was obtained in the same manner as in 11), a pattern was formed in the same manner as described above, and the characteristics thereof were examined.

[1064] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 133 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1065]

[Table 133] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-14) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 35:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was 45:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1067] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1067] The following examples (II-100) to examples (II
-107), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-14) was synthesized, and its characteristics were examined. (Example II-100) to (Example II-103) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-14) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1068] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 134 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1069]

[Table 134] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-104) to (Example II-107) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-14) was used. In Example (II-8) to Example described above, except that the dissolution inhibitor was changed to 3,3-bis-6′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isonaphthalenofuranone. Example (II-
A chemically amplified resist was obtained in the same manner as in 11), a pattern was formed in the same manner as described above, and the characteristics thereof were examined.

[1070] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 135 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1071]

[Table 135] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-15) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 35:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was set to 40:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1072] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1073] The following Examples (II-108) to Examples (II
-115), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-15) was synthesized, and its characteristics were examined. (Example II-108) to (Example II-111) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-15) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1074] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 136 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1075]

[Table 136] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-112) to (Example II-115) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-15) was used. In Example (II-8) to Example, except that the dissolution inhibitor was changed to 3,3-bis-7′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isonaphthalenofuranone. Example (II-
A chemically amplified resist was obtained in the same manner as in 11), a pattern was formed in the same manner as described above, and the characteristics thereof were examined.

[1076] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 137 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1077]

[Table 137] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-16) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid is 35:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was set to 35:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1078] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

The following Examples (II-116) to Examples (II
-123), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-16) was synthesized, and its characteristics were examined. (Example II-116) to (Example II-119) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-16) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1080] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 138 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1081]

[Table 138] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-120) to (Example II-123) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-16) is used. In Example (II-8) to Example, except that the dissolution inhibitor was changed to 3,3-bis-8′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isononaphthalenofuranone. Example (II-
A chemically amplified resist was obtained in the same manner as in 11), a pattern was formed in the same manner as described above, and the characteristics thereof were examined.

[1082] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 139 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1083]

[Table 139] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-17) The above-mentioned Synthesis Example (II-2) except that t-butyl methacrylate was changed to ethoxyethyl methacrylate and the ratio of menthyl methacrylate, ethoxyethyl methacrylate, and methacrylic acid was 35:30:35. A copolymer was obtained in the same manner as the above), and this was used as the same cyclohexanone solution as described above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1086] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1085] The following Examples (II-124) to Examples (II
-131), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-17) was synthesized, and its characteristics were examined. (Example II-124) to (Example II-127) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-17) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1086] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 140 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1087]

[Table 140] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-128) to (Example II-131) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-17) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1088] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 141 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1089]

[Table 141] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-18) The above Synthesis Example except that t-butyl methacrylate was changed to 3-oxocyclohexyl methacrylate and the ratio of menthyl methacrylate, 3-oxocyclohexyl methacrylate and methacrylic acid was 35:25:40. A copolymer was obtained in the same manner as in (II-2), and this was used as the same cyclohexanone solution as described above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1090] Further, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1091] The following Examples (II-132) to Examples (II
-139), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-18) was synthesized, and its characteristics were examined. (Example II-132) to (Example II-135) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-18) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1092] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 142 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1093]

[Table 142] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-136) to (Example II-139) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-18) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1094] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 143 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1095]

[Table 143] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-19) The t-butyl methacrylate was changed to t-butyl-3-naphthyl-propenoate, and the ratio of menthyl methacrylate, t-butyl-3-naphthyl-propenoate and methacrylic acid was 35: 20: 4.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-2) except that the number was 5, and this was used as the same cyclohexanone solution as described above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1096] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1097] The following Examples (II-140) to Examples (II
-147), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-19) was synthesized, and the characteristics thereof were examined. (Example II-140) to (Example II-143) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-19) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1098] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 144 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1099]

[Table 144] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-144) to (Example II-147) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-19) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1100] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 145 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1101]

[Table 145] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-20) The above-mentioned Synthesis Example (II) except that t-butyl methacrylate was changed to isobornyl methacrylate and the ratio of menthyl methacrylate, isobornyl methacrylate and methacrylic acid was set to 30:50:20. A copolymer was obtained in the same manner as in -2), and this was used as the same cyclohexanone solution as described above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1102] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1103] The following Examples (II-148) to Examples (II
-155), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-20) was synthesized, and its characteristics were examined. (Example II-148) to (Example II-151) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-20) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1104] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 146 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1105]

[Table 146] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-152) to (Example II-155) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-20) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1106] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 147 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1107]

[Table 147] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-21) The above-mentioned synthesis example (II) except that t-butyl methacrylate is changed to tetrahydropyranyl methacrylate and the ratio of menthyl methacrylate, tetrahydropyranyl methacrylate and methacrylic acid is set to 30:45:25. A copolymer was obtained in the same manner as in -2), and this was used as the same cyclohexanone solution as described above.
As a result of similarly examining the transparency with respect to the ArF excimer laser light (193 nm), the transmittance was 74%, and the P
It was superior to MMA.

[1108] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1109] The following Examples (II-156) to Examples (II
-163), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-21) was synthesized, and the characteristics thereof were examined. (Example II-156) to (Example II-159) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-21) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1110] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 148 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1111]

[Table 148] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-160) to (Example II-163) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-21) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1112] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 149 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1113]

[Table 149] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-22) Except that t-butyl methacrylate is changed to ethoxyethyl acrylate and the ratio of menthyl methacrylate, ethoxyethyl acrylate, and methacrylic acid is set to 30:40:30, the above-mentioned synthesis example (II-2). A copolymer was obtained in the same manner as the above), and this was used as the same cyclohexanone solution as described above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1114] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1115] The following Examples (II-164) to Examples (II
-171), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-22) was synthesized, and its characteristics were examined. (Example II-164) to (Example II-167) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-22) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1116] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 150 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1117]

[Table 150] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-168) to (Example II-171) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-22) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1118] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 151 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1119]

[Table 151] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-23) The above synthesis example except that t-butyl methacrylate was changed to 3-oxocyclohexyl acrylate and the ratio of menthyl methacrylate, 3-oxocyclohexyl acrylate, and methacrylic acid was 30:35:35. A copolymer was obtained in the same manner as in (II-2), and this was used as the same cyclohexanone solution as described above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1120] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1121] The following Examples (II-172) to Examples (II
-179), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-23) was synthesized, and its characteristics were examined. (Example II-172) to (Example II-175) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-23) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1122] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 152 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1123]

[Table 152] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-176) to (Example II-179) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-23) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1124] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 153 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1125]

[Table 153] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-24) Except that t-butyl methacrylate was changed to tetrahydropyranyl acrylate and the ratio of menthyl methacrylate, tetrahydropyranyl acrylate, and methacrylic acid was 30:30:40.
A copolymer was obtained in the same manner as in Synthesis Example (II-2) described above, and this was used as the same cyclohexanone solution as described above. ArF
As a result of similarly examining the transparency with respect to the excimer laser light (193 nm), the transmittance was 74%.
Was better.

[1126] Further, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-180) to Examples (II
-187), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-24) was synthesized, and its characteristics were examined. (Example II-180) to (Example II-183) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-24) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1128] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 154 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1129]

[Table 154] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-184) to (Example II-187) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-24) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1130] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 155 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1131]

[Table 155] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-25) The above-mentioned Synthesis Example (II) except that t-butyl methacrylate was changed to isobornyl acrylate and the ratio of menthyl methacrylate, isobornyl acrylate, and methacrylic acid was set to 30:25:45. A copolymer was obtained in the same manner as in -2), and this was used as the same cyclohexanone solution as described above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1132] Further, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1133] The following examples (II-188) to examples (II
-195), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-25) was synthesized, and its characteristics were examined. (Example II-188) to (Example II-191) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-25) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1134] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 156 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1135]

[Table 156] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-192) to (Example II-195) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-25) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1136] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 157 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1137]

[Table 157] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-26) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 30:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was set to 20:50, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1138] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1139] The following Examples (II-196) to Examples (II
-203), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-26) was synthesized, and its characteristics were examined. (Example II-196) to (Example II-199) Using a photo-acid generator shown in Table 158 below, a synthesis example (II-
Instead of the copolymer obtained in 2), Synthesis Example (II-26)
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), except that the copolymer obtained in (4) was used. A pattern was formed and its characteristics were investigated.

[1140] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 158 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1141]

[Table 158] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-200) to (Example II-203) Using a photo-acid generator shown in Table 159 below, a synthesis example (II-
Instead of the copolymer obtained in 2), Synthesis Example (II-26)
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11), except that the copolymer obtained in (4) was used. A pattern was formed and its characteristics were investigated.

[1142] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 159 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1143]

[Table 159] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-27) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-2) except that the ratio was set to 55:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1144] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1145] The following Examples (II-204) to Examples (II
-211), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-27) was synthesized, and its characteristics were examined. (Example II-204) to (Example II-207) Using a photo-acid generator shown in Table 160 below, a synthesis example (II-
Instead of the copolymer obtained in 2), Synthesis Example (II-27)
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), except that the copolymer obtained in (1) was used. A pattern was formed and its characteristics were investigated.

[1146] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 160 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1147]

[Table 160] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-208) to (Example II-211) Using the photo-acid generators shown in Table 161 below, Synthesis Example (II-
Instead of the copolymer obtained in 2), Synthesis Example (II-27)
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11), except that the copolymer obtained in (4) was used. A pattern was formed and its characteristics were investigated.

[1148] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 161 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1149]

[Table 161] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-28) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) above except that the ratio was set to 50:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1150] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1151] The following Examples (II-212) to Examples (II
-219), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-28) was synthesized, and its characteristics were examined. (Example II-212) to (Example II-215) Using a photo-acid generator shown in Table 162 below, a synthesis example (II-
Instead of the copolymer obtained in 2), Synthesis Example (II-28)
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), except that the copolymer obtained in (1) was used. A pattern was formed and its characteristics were investigated.

[1152] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 162 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1153]

[Table 162] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-216) to (Example II-219) Using a photo-acid generator shown in Table 163 below, a synthesis example (II-
Instead of the copolymer obtained in 2), Synthesis Example (II-28)
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11), except that the copolymer obtained in (4) was used. A pattern was formed and its characteristics were investigated.

[1154] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 163 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1155]

[Table 163] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-29) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was 45:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1156] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1157] The following Examples (II-220) to Examples (II
-227), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-29) was synthesized, and its characteristics were examined. (Example II-220) to (Example II-223) Using a photo-acid generator shown in Table 164 below, a synthesis example (II-
Instead of the copolymer obtained in 2), Synthesis Example (II-29)
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), except that the copolymer obtained in (1) was used. A pattern was formed and its characteristics were investigated.

[1158] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 164 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1159]

[Table 164] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-224) to (Example II-227) Using a photo-acid generator shown in Table 165 below, a synthesis example (II-
Instead of the copolymer obtained in 2), Synthesis Example (II-29)
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11), except that the copolymer obtained in (4) was used. A pattern was formed and its characteristics were investigated.

[1160] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 165 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1161]

[Table 165] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-30) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was 40:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1162] Further, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1163] The following Examples (II-228) to Examples (II
-235), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-30) was synthesized, and the characteristics thereof were examined. (Example II-228) to (Example II-231) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-30) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1164] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 166 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1165]

[Table 166] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-232) to (Example II-235) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-30) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1166] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 167 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1167]

[Table 167] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-31) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was set to 35:40, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1168] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1169] The following Examples (II-236) to Examples (II
-243), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-31) was synthesized, and its characteristics were examined. (Example II-236) to (Example II-239) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-31) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1170] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 168 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1171]

[Table 168] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-240) to (Example II-243) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-31) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1175] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 169 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1173]

[Table 169] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-32) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was set to 30:45, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1174] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1175] The following Examples (II-244) to Examples (II
-251), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-32) was synthesized, and its characteristics were examined. (Example II-244) to (Example II-247) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-32) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1176] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 170 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1177]

[Table 170] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-248) to (Example II-251) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-32) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1178] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 171 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1179]

[Table 171] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-33) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) except that the ratio was 25:50, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1180] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1181] The following Examples (II-252) to Examples (II
-259), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-33) was synthesized, and its characteristics were examined. (Example II-252) to (Example II-255) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-33) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1182] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 172 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1183]

[Table 172] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-256) to (Example II-259) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-33) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1184] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 173 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1185]

[Table 173] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-34) The ratio of menthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-2) above except that the ratio was set to 20:55, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1187] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1187] The following Examples (II-260) to Examples (II
-267), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-34) was synthesized, and its characteristics were examined. (Example II-260) to (Example II-263) The copolymer obtained in Synthesis Example (II-34) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1188] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 174 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1189]

[Table 174] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-264) to (Example II-267) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-34) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1190] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 175 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1191]

[Table 175] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-35) 16 g of maleic acid, 20 g of menthol, and 10 g of paratoluenesulfonic acid were added,
The mixture was refluxed by heating in 30 mL of toluene at an oil temperature of 150 ° C. for 10 hours. Then, the reaction was stopped with a saturated sodium hydrogen carbonate aqueous solution, and ether was added. The two layers were separated, the aqueous layer was extracted with ether, and the organic layers were combined and washed with a saturated aqueous sodium hydrogen carbonate solution to remove the acid. Further, the pH was adjusted to around 7 with a saturated ammonium chloride aqueous solution, and dried with saturated saline and anhydrous sodium sulfate. The resulting oily matter was fractionally distilled to obtain maleic acid monomenthyl ester and dimenthyl mariate.

[1192] Maleic acid monomenthyl ester 2.5 g and 2-methyl-2-propanol 1 g,
And 0.7 g of para-toluenesulfonic acid were refluxed in 30 mL of toluene at an oil temperature of 150 ° C. for 19 hours.
Then, the reaction was stopped with a saturated sodium hydrogen carbonate aqueous solution, and ether was added. The two layers were separated, the water bath was extracted with ether, and the organic layers were combined and saturated sodium bicarbonate was added.
And the acid was removed by washing with an aqueous sodium hydroxide solution.
Further, the pH was adjusted to 7 with a saturated aqueous solution of ammonium chloride, and dried with saturated saline and anhydrous sodium sulfate. The obtained oily substance was distilled under reduced pressure to give menthyl 3-t-
Butoxycarbonyl-2Z-propenoate was obtained. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example II-35) Menthyl 3-t-butoxycarbonyl-2Z-propenoate 10 g and polymerization initiator azoisobutyronitrile 0.5 g were added to THF 40 mL. Dissolved.

[1193] The obtained solution was frozen in liquid nitrogen, deaerated 5 times for 20 minutes, and then brought to room temperature. Next, under a nitrogen stream,
The oil temperature was heated at 60 ° C. for 10 hours, and the reaction was stopped with 600 mL of hexane. After reprecipitation with hexane, it was filtered off and the solvent was distilled off under vacuum to give polymenthyl 3-t-butoxycarbonyl-2Z-
Got propenoate.

[1196] Further, a polymerization reaction was performed under the same conditions as described above except that 10 g of dimenthyl mariate was used to obtain polydimenthyl mariate.

[1195] Further, a polymerization reaction was carried out under the same conditions as described above except that 10 g of maleic acid monomenthyl ester was used to obtain a polymeric acid monomenthyl ester.

[1196] Each polymer was used as a cyclohexanone solution, and treated in the same manner as in the case of the monomer of Synthesis Example (II-1).
The transparency for ArF excimer laser light (193 nm) was investigated. As a result, polymenthyl 3-t-butoxycarbonyl-2
The transmittance of Z-propenoate was 50%, and that of polydimenthyl mariate was 43%, which were similar to PMMA.

[1196] Furthermore, under the same conditions as in the case of the monomer of Synthesis Example (II-1) above, carbon tetrafluoride (CH
₄ ) The etching rate by gas was measured and compared with PMMA. As a result, when the etching rate of PMMA was 1, all polymers were excellent at 0.3.

[1196] In the following Examples, the above synthesis examples (II-3
The copolymers containing dimenthyl mariate, menthyl 3-t-butoxycarbonyl-2Z-propenoate, or maleic acid monomenthyl ester obtained in 5) were each synthesized to obtain a photosensitive composition containing them. And investigated its characteristics. Example II-268 5 g of dimenthyl mariate, 0.5 g of glycidyl methacrylate, and 0.25 g of azoisobutyronitrile as a polymerization initiator were dissolved in 15 mL of toluene.

[1199] The obtained solution was reacted in the same manner as in Example (II-1) above to obtain a target copolymer, and this copolymer was similarly converted into methyl 3-methoxypropionate. Dissolved. Using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

[1200] As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example II-269) 1 g of dimenthyl mariate, 0.1 g of allyl methacrylate, and 0.05 g of azoisobutyronitrile as a polymerization initiator were dissolved in 5 mL of toluene. The obtained solution was reacted in the same manner as in Example (II-2) described above to obtain a target copolymer, and this copolymer was similarly dissolved in methyl 3-methoxypropionate. Using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

[1201] As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example II-270) Dimenthyl mariate 1 g, a-
1 g of chlorotrifluoroacrylate and 0.1 g of azoisobutyronitrile as a polymerization initiator were dissolved in 3 mL of THF. The obtained solution was reacted in the same manner as in Example (II-3) above to obtain a target copolymer, and this copolymer was similarly dissolved in methyl 3-methoxypropionate. Using this, a pattern is formed in the same manner as above,
I investigated its characteristics.

[1202] As a result, a positive line and space pattern of 0.5 μm could be resolved. (Example II-271) Instead of dimenthyl mariate,
Menthyl 3-t-butoxycarbonyl-2Z-propenoate
A copolymer was obtained by the same procedure as in Example (II-268) except that 0.8 g was used. The obtained copolymer was made into a solution similar to that in Example (II-268), and a pattern was similarly formed using this solution.

[1203] As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example II-272) Instead of dimenthyl mariate,
Menthyl 3-t-butoxycarbonyl-2Z-propenoate
A copolymer was obtained by the same procedure as in Example (II-269) except that 0.8 g was used. The obtained copolymer was made into a solution similar to that in Example (II-269), and a pattern was similarly formed using this solution.

[1204] As a result, a negative line and space pattern of 0.5 µm could be resolved. (Example II-273) Instead of dimenthyl mariate,
Menthyl 3-t-butoxycarbonyl-2Z-propenoate
A copolymer was obtained by the same procedure as in Example (II-270) except that 0.8 g was used. The obtained copolymer was made into a solution similar to that in Example (II-270), and a pattern was similarly formed using this solution.

[1205] As a result, a positive line and space pattern of 0.5 μm could be resolved.

[1206] The following Examples (II-274) to Examples (II
-281), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-35) was synthesized, and its characteristics were examined. (Example II-274) to (Example II-277) Instead of the copolymer obtained in Synthesis Example (II-2), the homopolymer (Polymenthyl 3-) obtained in Synthesis Example (II-35) was used.
t-butoxycarbonyl-2Z-propenoate), except that the above-mentioned Examples (II-4) to (II-) are used.
A chemically amplified resist was obtained in the same manner as in 7), a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

[1207] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 176 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1208]

[Table 176] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-278) to (Example II-281) Instead of the copolymer obtained in Synthesis Example (II-2), the homopolymer (polymeric acid acid) obtained in Synthesis Example (II-35) was used. A chemically amplified resist was obtained in the same manner as in Example (II-8) to Example (II-11) except that a monomenthyl ester) was used, and a pattern was formed in the same manner as described above using the resist. Then, the characteristics were investigated. Further, the transparency and the dry etching resistance were evaluated in the same manner as in Synthesis Example (II-1). The obtained results are summarized in Table 177 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1209]

[Table 177] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-36) A copolymer similar to the above Synthesis Example (II-35) except that the ratio of menthyl 3-t-butoxycarbonyl-2Z-propenoate and methacrylic acid was 70:30. To obtain a cyclohexanone solution similar to the above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1210] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1211] The following Examples (II-282) to Examples (II
-289), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-36) was synthesized, and its characteristics were examined. (Example II-282) to (Example II-285) The copolymer obtained in Synthesis Example (II-36) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1212] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 178 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1213]

[Table 178] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-286) to (Example II-289) The copolymer obtained in Synthesis Example (II-36) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1214] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 179 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1215]

[Table 179] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-37) The above-mentioned synthesis example (II-35) except that the ratio of menthyl 3-t-butoxycarbonyl-2Z-propenoate and methacrylic acid is 75:25.
A copolymer was obtained in the same manner as above, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (19
As a result of similarly examining the transparency to 3 nm), the transmittance was 74%, which was superior to PMMA.

[1216] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1217] The following Examples (II-290) to Examples (II
-297), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-37) was synthesized, and its characteristics were examined. (Example II-290) to (Example II-293) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-37) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1218] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 180 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1219]

[Table 180] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-294) to (Example II-297) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-37) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1220] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 181 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1221]

[Table 181] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-38) The above synthesis example (II-35) except that the ratio of menthyl 3-t-butoxycarbonyl-2Z-propenoate and methacrylic acid is 80:20.
A copolymer was obtained in the same manner as above, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (19
As a result of similarly examining the transparency to 3 nm), the transmittance was 74%, which was superior to PMMA.

[1222] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1223] The following Examples (II-298) to Examples (II
-305), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-38) was synthesized, and its characteristics were examined. (Example II-298) to (Example II-301) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-38) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1224] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 182 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1225]

[Table 182] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-302) to (Example II-305) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-38) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1226] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 183 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1227]

[Table 183] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-39) The above-mentioned synthesis example (II-35) except that the ratio of menthyl 3-t-butoxycarbonyl-2Z-propenoate and methacrylic acid is 65:35.
A copolymer was obtained in the same manner as above, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (19
As a result of similarly examining the transparency to 3 nm), the transmittance was 74%, which was superior to PMMA.

Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-306) to Examples (II
313), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-39) was synthesized, and its characteristics were examined. (Example II-306) to (Example II-309) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-39) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1230] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 184 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1231]

[Table 184] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-310) to (Example II-313) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-39) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1232] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 185 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1233]

[Table 185] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-40) The above-mentioned synthesis example (II-35) except that the ratio of menthyl 3-t-butoxycarbonyl-2Z-propenoate and methacrylic acid is 60:40.
A copolymer was obtained in the same manner as above, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (19
As a result of similarly examining the transparency to 3 nm), the transmittance was 74%, which was superior to PMMA.

[1234] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-314) to Examples (II
-321), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-40) was synthesized, and its characteristics were investigated. (Example II-314) to (Example II-317) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-40) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1236] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 186 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1237]

[Table 186] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-318) to (Example II-321) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-40) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1238] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 187 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1239]

[Table 187] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-41) The above-mentioned synthesis example (II-35) except that the ratio of menthyl 3-t-butoxycarbonyl-2Z-propenoate and methacrylic acid is 55:45.
A copolymer was obtained in the same manner as above, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (19
As a result of similarly examining the transparency to 3 nm), the transmittance was 74%, which was superior to PMMA.

[1240] Furthermore, when the etching rate by carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-322) to Examples (II
-329), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-41) was synthesized, and the characteristics thereof were examined. (Example II-322) to (Example II-325) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-41) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1242] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 188 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1243]

[Table 188] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-326) to (Example II-329) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-41) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1244] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 189 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1245]

[Table 189] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-42) The above Synthesis Example (II-35) except that the ratio of menthyl 3-t-butoxycarbonyl-2Z-propenoate and methacrylic acid is 50:50.
A copolymer was obtained in the same manner as above, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (19
As a result of similarly examining the transparency to 3 nm), the transmittance was 74%, which was superior to PMMA.

[1246] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1247] The following Examples (II-330) to Examples (II
-337), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-42) was synthesized, and the characteristics thereof were examined. (Example II-330) to (Example II-333) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-42) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1248] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 190 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1249]

[Table 190] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-334) to (Example II-337) The copolymer obtained in Synthesis Example (II-42) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1250] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 191 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1251]

[Table 191] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-43) In this synthesis example, the synthesis example (II-
35) Another copolymer containing the monomer obtained in 35) was synthesized,
The evaluation was performed.

[1252] 10 g of dimenthyl mariate, t-butyl methacrylate, and methacrylic acid were prepared at a ratio of 35:40:25, and dissolved in 40 mL of THF together with 0.5 g of azoisobutyronitrile as a polymerization initiator.

[1253] The obtained solution was frozen in liquid nitrogen, deaerated 5 times for 20 minutes, and then brought to room temperature. Next, the mixture was heated at an oil temperature of 60 ° C. for 9 hours under a nitrogen stream, and the reaction was stopped with hexane. After reprecipitation with hexane, the mixture was filtered and the solvent was removed under vacuum to obtain the target copolymer, which was used as the same cyclohexane solution as described above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1254] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1255] The following Examples (II-338) to Examples (II
-345), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-43) was synthesized, and its characteristics were examined. (Example II-338) to (Example II-341) The copolymer obtained in Synthesis Example (II-43) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1256] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 192 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1257]

[Table 192] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-342) to (Example II-345) The copolymer obtained in Synthesis Example (II-43) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1258] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 193 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1259]

[Table 193] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-44) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 35:
32.5: 32.5 except that the synthesis example (II-
A copolymer was obtained in the same manner as in 43), and this was used as the same cyclohexanone solution as described above. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1260] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1261] The following Examples (II-346) to Examples (II
-353), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-44) was synthesized, and its characteristics were investigated. (Example II-346) to (Example II-349) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-44) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1262] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 194 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1263]

[Table 194] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-350) to (Example II-353) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-44) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1264] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 195 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1265]

[Table 195] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-45) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 35:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-43) except that the ratio was 25:40, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1266] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-354) to Examples (II
-361), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-45) was synthesized, and its characteristics were examined. (Example II-354) to (Example II-357) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-45) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1268] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 196 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1269]

[Table 196] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-358) to (Example II-361) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-45) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1270] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 197 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1271]

[Table 197] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-46) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 30:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 45:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1272] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1273] The following Examples (II-362) to Examples (II
-369), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-46) was synthesized, and its characteristics were investigated. (Example II-362) to (Example II-365) The copolymer obtained in Synthesis Example (II-46) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1274] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 198 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1275]

[Table 198] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-366) to (Example II-369) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-46) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1276] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 199 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1277]

[Table 199] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-47) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 30:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-43) except that the ratio was set to 40:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1278] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1279] The following Examples (II-370) to Examples (II
-377), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-47) was synthesized, and its characteristics were examined. (Example II-370) to (Example II-373) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-47) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1280] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 200 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1281]

[Table 200] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-374) to (Example II-377) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-47) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1282] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 201 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1283]

[Table 201] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-48) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 30:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 30:40, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1284] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1285] The following Examples (II-378) to Examples (II
-385), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-48) was synthesized, and its characteristics were examined. (Example II-378) to (Example II-381) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-48) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1286] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 202 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1287]

[Table 202] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-382) to (Example II-385) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-48) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1288] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 203 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1289]

[Table 203] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-49) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 30:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was 25:45, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1290] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1291] The following Examples (II-386) to Examples (II
-393), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-49) was synthesized and its characteristics were investigated. (Example II-386) to (Example II-389) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-49) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1292] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 204 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1293]

[Table 204] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-390) to (Example II-393) The copolymer obtained in Synthesis Example (II-49) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1294] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 205 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1295]

[Table 205] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-50) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 50:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1296] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1297] The following Examples (II-394) to Examples (II
-401), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-50) was synthesized, and its characteristics were examined. (Example II-394) to (Example II-397) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-50) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1298] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 206 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1299]

[Table 206] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-398) to (Example II-401) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-50) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1300] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 207 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1301]

[Table 207] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-51) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-43) except that the ratio was set to 45:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1302] Further, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1303] The following Examples (II-402) to Examples (II
-409), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-51) was synthesized, and its characteristics were examined. (Example II-402) to (Example II-405) The copolymer obtained in Synthesis Example (II-51) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1304] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 208 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1305]

[Table 208] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-406) to (Example II-409) The copolymer obtained in Synthesis Example (II-51) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1306] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 209 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1307]

[Table 209] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-52) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 40:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1308] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1309] The following Examples (II-410) to Examples (II
-417), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-52) was synthesized, and the characteristics thereof were examined. (Example II-410) to (Example II-413) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-52) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1310] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 210 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1311]

[Table 210] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-414) to (Example II-417) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-52) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1312] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 211 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1313]

[Table 211] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-53) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 30:45, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1314] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1315] The following Examples (II-418) to Examples (II
-425), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-53) was synthesized, and its characteristics were examined. (Example II-418) to (Example II-421) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-53) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1316] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 212 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1317]

[Table 212] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-422) to (Example II-425) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-53) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1318] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 213 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1319]

[Table 213] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-54) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 25:50, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

Further, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1321] The following Examples (II-426) to Examples (II
-433), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-54) was synthesized, and the characteristics thereof were examined. (Example II-426) to (Example II-429) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-54) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1332] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 214 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1323]

[Table 214] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-430) to (Example II-433) The copolymer obtained in Synthesis Example (II-54) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1324] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 215 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1325]

[Table 215] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-55) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was 55:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1326] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1327] The following Examples (II-434) to Examples (II
-441), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-55) was synthesized, and its characteristics were examined. (Example II-434) to (Example II-437) The copolymer obtained in Synthesis Example (II-55) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1327] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 216 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1329]

[Table 216] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-438) to (Example II-441) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-55) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1330] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 217 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1331]

[Table 217] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-56) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 50:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1332] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1333] The following Examples (II-442) to Examples (II
-449), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-56) was synthesized, and the characteristics thereof were examined. (Example II-442) to (Example II-445) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-56) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1334] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 218 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1335]

[Table 218] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-446) to (Example II-449) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-56) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1336] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 219 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1337]

[Table 219] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-57) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 40:40, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1338] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1339] The following Examples (II-450) to Examples (II
-457), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-57) was synthesized, and its characteristics were examined. (Example II-450) to (Example II-453) The copolymer obtained in Synthesis Example (II-57) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1340] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 220 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1341]

[Table 220] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-454) to (Example II-457) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-57) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1342] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 221 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1343]

[Table 221] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-58) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 35:45, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1344] Furthermore, when the etching rate by carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1345] The following Examples (II-458) to Examples (II
-465), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-58) was synthesized, and its characteristics were examined. (Example II-458) to (Example II-461) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-58) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1346] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 222 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1347]

[Table 222] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-462) to (Example II-465) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-58) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1349] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 223 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1349]

[Table 223] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-59) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 30:50, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1350] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1351] The following Examples (II-466) to Examples (II
-473), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-59) was synthesized, and the characteristics thereof were examined. (Example II-466) to (Example II-469) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-59) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1352] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 224 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1353]

[Table 224] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-470) to (Example II-473) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-59) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1354] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 225 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1355]

[Table 225] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-60) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was 25:55, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1356] Further, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1357] The following Examples (II-474) to Examples (II
-481), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-60) was synthesized, and its characteristics were examined. (Example II-474) to (Example II-477) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-60) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1358] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 226 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1359]

[Table 226] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-478) to (Example II-481) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-60) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1360] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 227 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1361]

[Table 227] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-61) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 60:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1362] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1363] The following Examples (II-482) to Examples (II
-489), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-61) was synthesized, and the characteristics thereof were examined. (Example II-482) to (Example II-485) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-61) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1364] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 228 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1365]

[Table 228] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-486) to (Example II-489) The copolymer obtained in Synthesis Example (II-61) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1366] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 229 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1367]

[Table 229] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-62) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was 45:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1368] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1369] The following Examples (II-490) to Examples (II
-497), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-62) was synthesized, and its characteristics were examined. (Example II-490) to (Example II-493) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-62) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1370] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 230 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1371]

[Table 230] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-494) to (Example II-497) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-62) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1372] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 231 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1373]

[Table 231] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-63) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 35:45, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1370] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1375] The following Examples (II-498) to Examples (II
-505), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-63) was synthesized, and its characteristics were examined. (Example II-498) to (Example II-501) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-63) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1376] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 232 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1377]

[Table 232] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-502) to (Example II-505) The copolymer obtained in Synthesis Example (II-63) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1378] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 233 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1379]

[Table 233] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-64) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 20:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 20:60, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1380] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1381] The following Examples (II-506) to Examples (II
-513), the chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-64) was synthesized, and its characteristics were investigated. (Example II-506) to (Example II-509) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-64) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1382] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 234 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1383]

[Table 234] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-510) to (Example II-513) The copolymer obtained in Synthesis Example (II-64) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1384] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 235 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1385]

[Table 235] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-65) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 15:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 60:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1386] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1387] The following Examples (II-514) to Examples (II
-521), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-65) was synthesized, and the characteristics thereof were examined. (Example II-514) to (Example II-517) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-65) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1388] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 236 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1389]

[Table 236] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-518) to (Example II-521) The copolymer obtained in Synthesis Example (II-65) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1390] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 237 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1391]

[Table 237] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-66) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 15:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-43) except that the ratio was set to 55:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1395] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1393] The following Examples (II-522) to Examples (II
-529), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-66) was synthesized, and its characteristics were investigated. (Example II-522) to (Example II-525) The copolymer obtained in Synthesis Example (II-66) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 238 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1395]

[Table 238] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-526) to (Example II-529) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-66) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1395] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 239 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1397]

[Table 239] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-67) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 15:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 50:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1398] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1399] The following Examples (II-530) to Examples (II
-537), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-67) was synthesized, and its characteristics were examined. (Example II-530) to (Example II-533) The copolymer obtained in Synthesis Example (II-67) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1400] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 240 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1401]

[Table 240] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-534) to (Example II-537) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-67) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1402] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 241 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1403]

[Table 241] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-68) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 15:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-43) except that the ratio was 45:40, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1404] Further, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1405] The following Examples (II-538) to Examples (II
-545), the chemically amplified resist containing the copolymer obtained in Synthesis Example (II-68) was synthesized, and its characteristics were examined. (Example II-538) to (Example II-541) The copolymer obtained in Synthesis Example (II-68) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1406] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 242 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1407]

[Table 242] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-542) to (Example II-545) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-68) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1408] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 243 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1409]

[Table 243] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-69) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 15:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 40:45, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1410] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

The following Examples (II-546) to Examples (II
In 553), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-69) was synthesized, and its characteristics were investigated. (Example II-546) to (Example II-549) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-69) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1412] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 244 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1413]

[Table 244] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-550) to (Example II-553) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-69) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1414] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 245 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1415]

[Table 245] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-70) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 15:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 35:50, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1416] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-554) to Examples (II
-561), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-70) was synthesized, and its characteristics were examined. (Example II-554) to (Example II-557) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-70) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1418] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 246 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1419]

[Table 246] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-558) to (Example II-561) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-70) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1420] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 247 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1421]

[Table 247] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-71) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 15:
A copolymer was obtained in the same manner as in Synthesis Example (II-43) except that the ratio was set to 30:55, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1422] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1423] The following Examples (II-562) to Examples (II
-569), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-71) was synthesized, and its characteristics were examined. (Example II-562) to (Example II-565) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-71) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1424] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 248 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1425]

[Table 248] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-566) to (Example II-569) The copolymer obtained in Synthesis Example (II-71) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1426] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 249 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1427]

[Table 249] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-72) The ratio of dimenthyl methacrylate, t-butyl methacrylate, and methacrylic acid was 15:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-43) except that the ratio was 25:60, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1436] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1429] The following Examples (II-570) to Examples (II
-577), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-72) was synthesized, and its characteristics were investigated. (Example II-570) to (Example II-573) The copolymer obtained in Synthesis Example (II-72) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1430] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 250 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1431]

[Table 250] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-574) to (Example II-577) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-72) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1432] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 251 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1433]

[Table 251] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-73) Acrylic acid 26 g, menthol 24
g, and 15 g of paratoluenesulfonic acid are added to toluene 5
The mixture was heated under reflux in 00 mL at an oil temperature of 150 ° C. for 19 hours. Then, the reaction was stopped with a saturated sodium hydrogen carbonate aqueous solution, and ether was added. The two layers were separated and the aqueous layer was extracted with ether, the organic layers were combined and then washed with saturated aqueous sodium hydrogen carbonate solution and aqueous sodium hydroxide solution to remove the acid. Furthermore, using saturated aqueous ammonium chloride solution,
H was adjusted to 7 and dried with saturated saline and anhydrous sodium sulphate. The finally obtained oily substance was distilled under reduced pressure to obtain menthyl acrylate. (Evaluation of Homopolymer Comprising Monomer Obtained in Synthesis Example II-73) 5 g of menthyl acrylate and 0.25 g of azoisobutyronitrile as a polymerization initiator were added to THF20.
Dissolved in mL.

[1434] The obtained solution was frozen in liquid nitrogen, deaerated three times for 20 minutes, and then brought to room temperature. Then, under a nitrogen stream, the oil temperature was heated at 70 ° C for 16 hours to obtain 600 m of methanol
The reaction was stopped by L. After reprecipitation with methanol, it was filtered off and the solvent was distilled off under vacuum to obtain polymenthyl acrylate.

[1435] After this was made into a cyclohexanone solution, the transparency to ArF excimer laser light (193 nm) was examined in the same manner as in the case of the monomer of Synthesis Example (II-1). As a result, the transmittance was 43%. It was equivalent to PMMA.

[1436] Further, under the same conditions as in the case of the monomer of Synthesis Example (II-1), carbon tetrafluoride (CH
₄ ) As a result of measuring the etching rate by gas and comparing with PMMA, if the etching rate of PMMA is 1,
Polymenthyl acrylate was excellent at 0.3.

[1437] Hereinafter, Example (II-579) to Example (II
-581), the copolymers containing menthyl acrylate obtained in Synthesis Example (II-73) were synthesized, and a photosensitive composition containing them was obtained to examine the characteristics. (Example II-579) Menthyl acrylate 9 g, glycidyl methacrylate 1 g, and azoisobutyronitrile 0.5 g as a polymerization initiator were added to toluene.
Dissolved in 30 mL.

[1438] The obtained solution was reacted in the same manner as in the above Example (II-1) to obtain a target copolymer, and this copolymer was similarly converted into methyl 3-methoxypropionate. Dissolved. Using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

As a result, a negative line and space pattern of 0.5 μm could be resolved. (Example II-580) Menthyl acrylate 9 g, allyl methacrylate 1 g, and azoisobutyronitrile 0.5 g as a polymerization initiator were added to toluene 30.
Dissolved in mL.

[1440] The obtained solution was reacted in the same manner as in Example (II-2) to obtain a target copolymer, and this copolymer was similarly converted into methyl 3-methoxypropionate. Dissolved. Using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

[1441] As a result, a negative line and space pattern of 0.5 µm could be resolved. (Example II-581) Menthyl acrylate 5 g, α
5 g of chlorotrifluoroethyl acrylate and 0.5 g of azoisobutyronitrile as a polymerization initiator
Was dissolved in 28 mL of THF.

[1442] The obtained solution was reacted in the same manner as in the above Example (II-3) to obtain a target copolymer, and this copolymer was similarly converted into methyl 3-methoxypropionate. Dissolved. Using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

As a result, it was possible to resolve a positive line and space pattern of 0.5 μm. (Synthesis Example II-74) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (II-73) was synthesized and evaluated.

[1444] Menthyl acrylate, t-butyl methacrylate, and methacrylic acid were prepared at a ratio of 50:30:20 in an amount of 10 g and dissolved in 40 mL of THF together with 0.5 g of azoisobutyronitrile as a polymerization initiator.

[1445] The obtained solution was frozen in liquid nitrogen, deaerated 5 times for 20 minutes, and then brought to room temperature. Next, the mixture was heated at an oil temperature of 60 ° C. for 9 hours under a nitrogen stream, and the reaction was stopped with hexane. After reprecipitation with hexane, filtration was performed and the solvent was removed under vacuum to obtain a copolymer. This is the above-mentioned synthesis example
The same cyclohexanone solution as in 1) was prepared. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1446] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-582) to Examples (II
-589), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-74) was synthesized, and its characteristics were examined. (Example II-582) to (Example II-585) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-74) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1480] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 252 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1449]

[Table 252] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-586) to (Example II-589) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-74) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1450] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 253 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1451]

[Table 253] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-75) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 50: 2.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 5:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1452] Further, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1453] The following Examples (II-590) to Examples (II
-597), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-75) was synthesized, and its characteristics were examined. (Example II-590) to (Example II-593) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-75) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1454] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 254 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1455]

[Table 254] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-594) to (Example II-597) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-75) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1456] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 255 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1457]

[Table 255] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-76) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 50: 2.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was set to 0:30. This was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1458] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1459] The following examples (II-598) to examples (II
-605), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-76) was synthesized, and its characteristics were examined. (Example II-598) to (Example II-601) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-76) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1460] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 256 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1461]

[Table 256] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-602) to (Example II-605) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-76) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1462] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The results obtained are summarized in Table 257 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1463]

[Table 257] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-77) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 45: 3.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 5:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1464] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1465] The following Examples (II-606) to Examples (II
-613), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-77) was synthesized, and its characteristics were examined. (Example II-606) to (Example II-609) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-77) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1466] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 258 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1467]

[Table 258] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-610) to (Example II-613) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-77) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1468] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 259 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1469]

[Table 259] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-78) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 45: 3.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was 0:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1470] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-614) to Examples (II
-621), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-78) was synthesized, and its characteristics were examined. (Example II-614) to (Example II-617) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-78) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1472] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 260 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1473]

[Table 260] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-618) to (Example II-621) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-78) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1474] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 261 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1475]

[Table 261] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-79) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 45: 2.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was set to 5:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1476] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1477] The following Examples (II-622) to Examples (II
-629), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-79) was synthesized, and its characteristics were examined. (Example II-622) to (Example II-625) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-79) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1478] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 262 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1479]

[Table 262] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-626) to (Example II-629) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-79) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1480] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 263 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1481]

[Table 263] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-80) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 45: 2.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 0:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1482] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1483] The following Examples (II-630) to Examples (II
-637), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-80) was synthesized, and its characteristics were examined. (Example II-630) to (Example II-633) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-80) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1484] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 264 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1485]

[Table 264] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-634) to (Example II-637) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-80) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1485] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 265 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1487]

[Table 265] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-81) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 40: 4.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was 0:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1488] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1489] The following Examples (II-638) to Examples (II
-645), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-81) above was synthesized, and its characteristics were examined. (Example II-638) to (Example II-641) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-81) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1490] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 266 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1491]

[Table 266] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-642) to (Example II-645) The copolymer obtained in Synthesis Example (II-81) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1494] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 267 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1493]

[Table 267] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-82) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 40: 3.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 5:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1494] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-646) to Examples (II
-653), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-82) was synthesized, and its characteristics were examined. (Example II-646) to (Example II-649) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-82) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1496] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 268 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1497]

[Table 268] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-650) to (Example II-653) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-82) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1498] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 269 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1499]

[Table 269] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-83) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 40: 3.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was set to 0:30. This was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1500] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-654) to Examples (II
-661), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-83) was synthesized, and its characteristics were examined. (Example II-654) to (Example II-657) The copolymer obtained in Synthesis Example (II-83) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1502] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 270 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1503]

[Table 270] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-658) to (Example II-661) The copolymer obtained in Synthesis Example (II-83) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1504] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 271 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1505]

[Table 271] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-84) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 40: 2.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 5:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1506] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1507] The following Examples (II-662) to Examples (II
-669), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-84) was synthesized, and its characteristics were examined. (Example II-662) to (Example II-665) The copolymer obtained in Synthesis Example (II-84) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1508] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 272 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1509]

[Table 272] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-666) to (Example II-669) The copolymer obtained in Synthesis Example (II-84) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1510] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 273 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1511]

[Table 273] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-85) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 40: 2.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was 0:40, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1512] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1513] The following Examples (II-670) to Examples (II
-677), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-85) was synthesized, and its characteristics were examined. (Example II-670) to (Example II-673) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-85) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1514] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 274 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1515]

[Table 274] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-674) to (Example II-677) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-85) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1516] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 275 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1517]

[Table 275] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-86) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 35: 4.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 5:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1518] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1519] The following Examples (II-678) to Examples (II
-685), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-86) was synthesized, and its characteristics were examined. (Example II-678) to (Example II-681) The copolymer obtained in Synthesis Example (II-86) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1520] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 276 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1521]

[Table 276] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-682) to (Example II-685) The copolymer obtained in Synthesis Example (II-86) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1522] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 277 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1523]

[Table 277] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-87) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid was 35: 4.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was 0:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1524] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1525] The following Examples (II-686) to Examples (II
-693), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-87) was synthesized, and its characteristics were examined. (Example II-686) to (Example II-689) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-87) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1526] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 278 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1527]

[Table 278] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-690) to (Example II-692) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-87) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1528] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 279 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1529]

[Table 279] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-88) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid was 35: 3.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was set to 5:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1530] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1531] The following Examples (II-694) to Examples (II
-701), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-88) was synthesized, and its characteristics were examined. (Example II-694) to (Example II-697) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-88) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1532] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 280 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1533]

[Table 280] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-698) to (Example II-701) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-88) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1534] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 281 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1535]

[Table 281] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-89) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid was 35: 3.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 0:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1537] The following Examples (II-702) to (II)
-709), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-89) was synthesized, and its characteristics were examined. (Example II-702) to (Example II-705) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-89) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1538] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 282 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1539]

[Table 282] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-706) to (Example II-709) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-89) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1540] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 283 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1541]

[Table 283] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-90) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 35: 2.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 5:40, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1542] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1543] The following Examples (II-710) to Examples (II
-717), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-90) was synthesized, and its characteristics were examined. (Example II-710) to (Example II-713) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-90) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1544] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 284 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1545]

[Table 284] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-714) to (Example II-717) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-90) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1546] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 285 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1547]

[Table 285] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-91) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 35: 2.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was 0:45, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1548] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1549] The following Examples (II-718) to Examples (II
-725), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-91) was synthesized, and its characteristics were examined. (Example II-718) to (Example II-721) The copolymer obtained in Synthesis Example (II-91) is used instead of the copolymer obtained in Synthesis Example (II-2). Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1550] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 286 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1551]

[Table 286] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-722) to (Example II-725) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-91) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1552] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 287 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1553]

[Table 287] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-92) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid was 30: 5.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was 0:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

Further, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1555] The following Examples (II-726) to Examples (II
-733), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-92) was synthesized, and its characteristics were examined. (Example II-726) to (Example II-729) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-92) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1556] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 288 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1557]

[Table 288] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-730) to (Example II-733) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-92) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1558] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 289 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1559]

[Table 289] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-93) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 30: 4.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 5:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

Further, comparing the etching rate of carbon tetrafluoride gas (CH ₄ ) gas with PMMA under the same conditions as above, when the etching rate of PMMA is 1, this copolymer is excellent at 0.3. Was there.

[1561] The following Examples (II-734) to Examples (II
-741), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-93) was synthesized, and its characteristics were examined. (Example II-734) to (Example II-737) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-93) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1562] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 290 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1563]

[Table 290] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-738) to (Example II-741) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-93) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1564] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 291 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1565]

[Table 291] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-94) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 30: 4.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was set to 0:30. This was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

Further, comparing the etching rate of carbon tetrafluoride gas (CH ₄ ) gas with that of PMMA under the same conditions as described above, when the etching rate of PMMA is 1, this copolymer is excellent at 0.3. Was there.

[1567] The following Examples (II-742) to Examples (II
-749), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-94) was synthesized, and its characteristics were investigated. (Example II-742) to (Example II-745) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-94) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1568] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 292 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1569]

[Table 292] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-746) to (Example II-749) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-94) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1570] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 293 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1571]

[Table 293] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-95) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 30: 3.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 5:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1572] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1573] The following Examples (II-750) to Examples (II
-757), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-95) was synthesized, and its characteristics were investigated. (Example II-750) to (Example II-753) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-95) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1574] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 294 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1575]

[Table 294] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-754) to (Example II-757) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-95) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1576] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 295 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1577]

[Table 295] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-96) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 30: 3.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was 0:40, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1580] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1579] The following Examples (II-758) to Examples (II
-765), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-96) was synthesized, and its characteristics were examined. (Example II-758) to (Example II-761) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-96) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1580] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 296 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1581]

[Table 296] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-762) to (Example II-765) The copolymer obtained in Synthesis Example (II-96) is used instead of the copolymer obtained in Synthesis Example (II-2). A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1582] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 297 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1583]

[Table 297] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-97) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 30: 2.
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was set to 5:45, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

[1584] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1585] The following Examples (II-766) to Examples (II
-773), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-97) was synthesized, and its characteristics were investigated. (Example II-766) to (Example II-769) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-97) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1586] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 298 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1587]

[Table 298] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-770) to (Example II-773) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-97) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1588] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 299 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1589]

[Table 299] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-98) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 30: 2.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was 0:50, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1591] The following examples (II-774) to examples (II
-781), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-98) was synthesized, and its characteristics were examined. (Example II-774) to (Example II-777) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-98) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1592] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 300 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1593]

[Table 300] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-778) to (Example II-781) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-98) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1594] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 301 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1595]

[Table 301] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-99) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 25: 5.
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 5:20, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193n
As a result of similarly examining the transparency with respect to m), the transmittance was 74%, which was superior to PMMA.

Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1597] The following Examples (II-782) to Examples (II
-789), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-99) was synthesized, and its characteristics were examined. (Example II-782) to (Example II-785) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-99) is used. Other than that, a chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1598] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 302 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1599]

[Table 302] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-786) to (Example II-789) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-99) is used. A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-8) to (II-11) except for the above, a pattern was formed in the same manner as described above, and its characteristics were examined. .

[1600] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 303 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1601]

[Table 303] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-100) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 25:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was set to 50:25, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1602] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1603] The following Examples (II-790) to Examples (II
-797), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-100) was synthesized, and its characteristics were investigated. (Example II-790) to (Example II-793) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-100) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1604] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 304 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1605]

[Table 304] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-794) to (Example II-797) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-100) is used. except,
A chemically amplified resist was obtained in the same manner as in the above Examples (II-8) to (II-11), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1606] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 305 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1607]

[Table 305] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-101) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 25:
A copolymer was obtained in the same manner as in the above-mentioned synthesis example (II-74) except that the ratio was set to 45:30, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1606] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1609] The following Examples (II-798) to Examples (II
-805), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-101) was synthesized, and its characteristics were examined. (Example II-798) to (Example II-801) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-101) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1610] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 306 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1611]

[Table 306] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-802) to (Example II-805) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-101) is used. except,
A chemically amplified resist was obtained in the same manner as in the above Examples (II-8) to (II-11), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1612] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 307 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1613]

[Table 307] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-102) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was 40:35, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1614] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1615] The following Examples (II-806) to Examples (II
In -813), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-102) was synthesized, and its characteristics were examined. (Example II-806) to (Example II-809) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-102) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1616] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 308 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1617]

[Table 308] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-810) to (Example II-813) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-102) is used. except,
A chemically amplified resist was obtained in the same manner as in the above Examples (II-8) to (II-11), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1618] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 309 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1619]

[Table 309] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-103) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was set to 35:40, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1620] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1621] The following Examples (II-814) to Examples (II
-821), a chemically amplified resist containing the copolymer obtained in the above Synthesis Example (II-103) was synthesized, and its characteristics were examined. (Example II-814) to (Example II-817) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-103) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1622] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 310 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1623]

[Table 310] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-818) to (Example II-821) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-103) is used. except,
A chemically amplified resist was obtained in the same manner as in the above Examples (II-8) to (II-11), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1624] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 311 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1625]

[Table 311] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-104) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 25:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was set to 30:45, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1626] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there.

[1627] The following Examples (II-822) to Examples (II
-829), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-104) was synthesized, and its characteristics were examined. (Example II-822) to (Example II-825) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-104) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1628] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 312 below together with the photo-acid generator used. The etching rate is a value for PMMA.

[1629]

[Table 312] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-826) to (Example II-829) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-104) is used. except,
A chemically amplified resist was obtained in the same manner as in the above Examples (II-8) to (II-11), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1630] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 313 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1631]

[Table 313] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-105) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 25:
A copolymer was obtained in the same manner as in Synthesis Example (II-74) except that the ratio was 25:50, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1632] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

[1633] The following Examples (II-830) to Examples (II
In -837), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-105) was synthesized, and its characteristics were examined. (Example II-830) to (Example II-833) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-105) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1636] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 314 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1635]

[Table 314] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-834) to (Example II-837) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-105) is used. except,
A chemically amplified resist was obtained in the same manner as in the above Examples (II-8) to (II-11), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1636] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 315 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1637]

[Table 315] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis example II-106) The ratio of menthyl acrylate, t-butyl methacrylate, and methacrylic acid is 25:
A copolymer was obtained in the same manner as in the above Synthesis Example (II-74) except that the ratio was set to 20:55, and this was used as the same cyclohexanone solution as described above. ArF excimer laser light (193
As a result of similarly examining the transparency to (nm), the transmittance was 74%, which was superior to PMMA.

[1638] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there.

The following Examples (II-838) to Examples (II
-845), a chemically amplified resist containing the copolymer obtained in Synthesis Example (II-106) was synthesized, and its characteristics were examined. (Example II-838) to (Example II-841) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-106) is used. except,
A chemically amplified resist was obtained in the same manner as in the above-mentioned Examples (II-4) to (II-7), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1640] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 316 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1641]

[Table 316] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example II-842) to (Example II-845) The copolymer obtained in Synthesis Example (II-106) is used instead of the copolymer obtained in Synthesis Example (II-2). except,
A chemically amplified resist was obtained in the same manner as in the above Examples (II-8) to (II-11), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1641] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 317 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1643]

[Table 317] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-107) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (II-1) was synthesized and evaluated.

[1644] Menthyl methacrylate and methacrylic acid were prepared at a ratio of 30:70 in an amount of 10 g, and T was added together with 0.5 g of azoisobutyronitrile as a polymerization initiator.
It was dissolved in 40 mL of HF.

[1645] The obtained solution was frozen in liquid nitrogen, deaerated 5 times for 20 minutes, and then brought to room temperature. Next, the mixture was heated at an oil temperature of 60 ° C. for 9 hours under a nitrogen stream, and the reaction was stopped with hexane. After reprecipitation with hexane, filtration was performed and the solvent was removed under vacuum to obtain a copolymer. This is the above-mentioned synthesis example
The same cyclohexanone solution as in 1) was prepared. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1646] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-846) to (Example II-849) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-107) is used. except,
A chemically amplified resist was obtained in the same manner as in the above Examples (II-8) to (II-11), a pattern was formed in the same manner as described above, and its characteristics were examined.

[1647] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 318 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1648]

[Table 318] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-108) A copolymer was obtained in the same manner as in the above Synthesis Example (II-107) except that the ratio of menthyl methacrylate to methacrylic acid was changed to 35:65. And The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1649] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with that of PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-850) to (Example II-853) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-108) is used. , Except that the dissolution inhibitor was changed to 3,3-bis-3′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone, the above-mentioned Examples (II-8) to Examples (II-1
A chemically amplified resist was obtained in the same manner as in 1), and using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

[1650] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 319 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1651]

[Table 319] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-109) A copolymer was obtained in the same manner as in the above Synthesis Example (II-107) except that the ratio of menthyl methacrylate to methacrylic acid was changed to 40:60. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-854) to (Example II-857) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-109) was used. , Except that the dissolution inhibitor was changed to 3,3-bis-2′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone, the above-mentioned Examples (II-8) to Examples (II-1
A chemically amplified resist was obtained in the same manner as in 1), and using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

[1653] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 320 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1654]

[Table 320] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-110) A copolymer was obtained in the same manner as in the above Synthesis Example (II-107), except that the ratio of menthyl methacrylate to methacrylic acid was changed to 45:55. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1655] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there. (Example II-858) to (Example II-861) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-110) was used. In Example (II-8) to Example described above, except that the dissolution inhibitor was changed to 3,3-bis-5'-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone. Example (II
A chemically amplified resist was obtained in the same manner as in (-11), and a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

[1656] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 321 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1657]

[Table 321] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-111) A copolymer was obtained in the same manner as in the above Synthesis Example (II-107), except that the ratio of menthyl methacrylate to methacrylic acid was changed to 50:50. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1658] Further, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-862) to (Example II-865) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-111) was used. In Example (II-8) to Example described above, except that the dissolution inhibitor was changed to 3,3-bis-6'-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone. Example (II
A chemically amplified resist was obtained in the same manner as in (-11), and a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

[1659] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 322 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1660]

[Table 322] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-112) A copolymer was obtained in the same manner as in the above Synthesis Example (II-107), except that the ratio of menthyl methacrylate to methacrylic acid was changed to 55:45. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1661] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there. (Example II-866) to (Example II-869) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-112) was used. In Example (II-8) to Example, except that the dissolution inhibitor was changed to 3,3-bis-7'-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone. Example (II
A chemically amplified resist was obtained in the same manner as in (-11), and a pattern was formed in the same manner as described above using the resist, and the characteristics thereof were examined.

[1662] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 323 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1663]

[Table 323] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-113) A copolymer was obtained in the same manner as in the above Synthesis Example (II-107), except that the ratio of menthyl methacrylate to methacrylic acid was changed to 60:40. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-870) to (Example II-873) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-113) was used. In Example (II-8) to Example, except that the dissolution inhibitor was changed to 3,3-bis-8′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone. Example (II
A chemically amplified resist was obtained in the same manner as in (-11), and a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

[1655] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 324 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1666]

[Table 324] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-114) In this Synthesis Example, another copolymer containing the monomer obtained in the above Synthesis Example (II-73) was synthesized and evaluated.

[1667] Menthyl acrylate and methacrylic acid were prepared in an amount of 30:70 in an amount of 10 g, and TH was added together with 0.5 g of azoisobutyronitrile as a polymerization initiator.
It was dissolved in 40 mL of F.

[1668] The obtained solution was frozen in liquid nitrogen, deaerated 5 times for 20 minutes, and then brought to room temperature. Next, the mixture was heated at an oil temperature of 60 ° C. for 9 hours under a nitrogen stream, and the reaction was stopped with hexane. After reprecipitation with hexane, filtration was performed and the solvent was removed under vacuum to obtain a copolymer. This is the above-mentioned synthesis example
The same cyclohexanone solution as in 1) was prepared. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1669] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-874) to (Example II-877) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-114) was used. , Except that the dissolution inhibitor is changed to 3,3-bis-1′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isononaphthalenofuranone. A chemically amplified resist was obtained in the same manner as in Example (II-11), and using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

[1670] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 325 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1671]

[Table 325] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-115) A copolymer was obtained in the same manner as in the above Synthesis Example (II-114) except that the ratio of menthyl acrylate and methacrylic acid was changed to 35:65. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1672] Furthermore, when the etching rate by carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-878) to (Example II-881) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-115) was used. , Except that the dissolution inhibitor is 3,3-bis-2′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isononaphthalenofuranone, the above-mentioned Examples (II-8) to ( II-1
A chemically amplified resist was obtained in the same manner as in 1), and using this, a pattern was formed in the same manner as described above, and its characteristics were examined.

[1670] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 326 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1674]

[Table 326] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-116) A copolymer was obtained in the same manner as in the above Synthesis Example (II-114) except that the ratio of menthyl acrylate and methacrylic acid was changed to 40:60. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1675] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-882) to (Example II-885) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-116) is used. , Except that the dissolution inhibitor was changed to 3,3-bis-3′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isononaphthalenofuranone. Example (II
A chemically amplified resist was obtained in the same manner as in (-11), and a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

[1676] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 327 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1677]

[Table 327] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-117) A copolymer was obtained in the same manner as in the above Synthesis Example (II-114) except that the ratio of menthyl acrylate and methacrylic acid was changed to 45:55. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1679] Furthermore, when the etching rate with carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent with 0.3. Was there. (Example II-886) to (Example II-889) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-117) is used. , Except that the dissolution inhibitor was changed to 3,3-bis-4'-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isononaphthalenofuranone. Example (II
A chemically amplified resist was obtained in the same manner as in (-11), and a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

[1679] Further, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 328 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1680]

[Table 328] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-118) A copolymer was obtained in the same manner as in the above Synthesis Example (II-114) except that the ratio of menthyl acrylate and methacrylic acid was changed to 50:50. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1681] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as described above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-890) to (Example II-893) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-118) was used. In Example (II-8) to Example, except that the dissolution inhibitor was changed to 3,3-bis-5′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isonaphthalenofuranone. Example (II
A chemically amplified resist was obtained in the same manner as in (-11), and a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

[1682] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 329 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1683]

[Table 329] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-119) A copolymer was obtained in the same manner as in the above Synthesis Example (II-114) except that the ratio of menthyl acrylate and methacrylic acid was changed to 55:45. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1684] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-894) to (Example II-897) The copolymer obtained in Synthesis Example (II-119) was used in place of the copolymer obtained in Synthesis Example (II-2). In Example (II-8) to Example described above, except that the dissolution inhibitor was changed to 3,3-bis-6′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isonaphthalenofuranone. Example (II
A chemically amplified resist was obtained in the same manner as in (-11), and a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

[1685] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 330 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1686]

[Table 330] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Synthesis Example II-120) A copolymer was obtained in the same manner as in the above Synthesis Example (II-114) except that the ratio of menthyl acrylate and methacrylic acid was changed to 60:40. It was a cyclohexanone solution. The transparency for ArF excimer laser light (193 nm) was examined in the same manner, and as a result, the transmittance was 74%, which was superior to PMMA.

[1687] Furthermore, when the etching rate of carbon tetrafluoride gas (CH ₄ ) gas was compared with PMMA under the same conditions as above, when the etching rate of PMMA was 1, this copolymer was excellent at 0.3. Was there. (Example II-898) to (Example II-901) Instead of the copolymer obtained in Synthesis Example (II-2), the copolymer obtained in Synthesis Example (II-120) was used. In Example (II-8) to Example, except that the dissolution inhibitor was changed to 3,3-bis-7′-t-butoxycarbonyloxynaphthalenyl-1 (3H) -isonaphthalenofuranone. Example (II
A chemically amplified resist was obtained in the same manner as in (-11), and a pattern was formed in the same manner as described above using the resist, and its characteristics were examined.

[1688] Furthermore, in the same manner as in Synthesis Example (II-1),
The transparency and dry etching resistance were evaluated. The obtained results are summarized in Table 331 below together with the photoacid generator used. The etching rate is a value for PMMA.

[1689]

[Table 331] In each of the examples, a line and space pattern of 0.15 μm could be obtained. (Example III) In this example, a compound having a terpenoid skeleton was used as a photoacid generator, a chemically amplified resist was synthesized, and its characteristics were evaluated. (Synthesis Example III-1) Menthyl mercaptomethane (10 g) was dissolved in nitromethane (30 mL). 54 g of iodomethane was added dropwise to this solution. After stirring at room temperature for 1 hour, 12 g of silver trifluoromethanesulfonate dissolved in 200 mL of nitromethane was added dropwise to this solution.
After stirring for 15 hours, the mixture was filtered, the filtrate was concentrated, ether was added, and the mixture was finally recrystallized to obtain colorless menthyldimethylsulfonium triflate. (Synthesis Example III-2) Methacrylic acid 24 g, menthol 31
g and 15 g of paratoluenesulfonic acid were heated to reflux in 500 mL of toluene at an oil temperature of 150 ° C. for 19 hours.
Then, the reaction was stopped with a saturated sodium hydrogen carbonate aqueous solution, and ether was added. The two layers were separated and the aqueous layer was extracted with ether, the organic layers were combined and then washed with saturated aqueous sodium hydrogen carbonate solution and aqueous sodium hydroxide solution to remove the acid. Further, the pH was adjusted to 7 with a saturated ammonium chloride aqueous solution, and dried with saturated saline and anhydrous sodium sulfate. The finally obtained oily substance was distilled under reduced pressure to obtain menthyl methacrylate.

[1690] 2.1 g of menthyl methacrylate and 0.4 g of azoisobutyronitrile as a polymerization initiator were dissolved in 6 mL of toluene.

[1691] The obtained solution was frozen in liquid nitrogen, deaerated three times for 20 minutes, and then brought to room temperature. Then, under a nitrogen stream, the oil temperature was heated at 70 ° C for 16 hours to obtain 600 m of methanol
The reaction was stopped by L. After reprecipitation with methanol, it was filtered off and the solvent was distilled off under vacuum to obtain polymenthyl methacrylate. (Evaluation of Photoacid Generator Obtained in Synthesis Example III-1) Polymenthyl Methacrylate 1 Obtained in Synthesis Example (III-2)
g, and 0.1 g of menthyl dimethyl sulfonium triflate as a photo-acid generator obtained in the above Synthesis Example (III-1) were used as a cyclohexanone solution. Then, it was applied on a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was examined. When converted into 1 μm, a transmittance of 50% was obtained at 193 nm.

Also, instead of menthyl dimethyl sulfonium triflate, 0.1 g of triphenyl sulfonium hexafluoroantimonate was used, and 1 g of polymenthyl methacrylate was added thereto to prepare a cyclohexanone solution, which was used as Comparative Example (III-1). .

The obtained solution of Comparative Example (III-1) was applied on a quartz wafer in the same manner and the transparency to ArF excimer laser light was examined.
The transmittance was 5% at 3 nm.

As a result, the photoacid generator having a terpenoid skeleton had a high transmittance at 193 nm even when used at 10%, whereas the photoacid generator containing a benzene ring had a significantly low transmittance. Recognize.

[1695] Hereinafter, Examples (III-1) to (III-
In 54), a chemically amplified resist containing various copolymers and the menthyl dimethylsulfonium triflate obtained in the above-mentioned Synthesis Example (III-1) as a photoacid generator was obtained, and its properties were evaluated. Examined. (Example III-1) Menthyl methacrylate, t-butyl methacrylate, and methacrylic acid were added at 30:30:
10 g was prepared at a ratio of 40 and dissolved in 40 mL of THF together with 0.5 g of azoisobutyronitrile as a polymerization initiator. The resulting solution was frozen in liquid nitrogen, degassed 5 times for 20 minutes, and then brought to room temperature. Next, under a nitrogen stream,
The oil temperature was heated at 60 ° C. for 9 hours, and the reaction was stopped with hexane. After reprecipitation with hexane, the product was filtered off and the solvent was removed under vacuum to obtain a target copolymer.

[1696] 2 g of this copolymer and 0.04 g of menthyl dimethyl sulfonium triflate as a photoacid generator.
And were dissolved in 8 mL of 2-ethoxyethyl acetate. This was applied on a silicon wafer to a film thickness of 0.8 μm and then prebaked at 100 ° C. Then, after performing ArF excimer laser exposure (40 mJcm ⁻² ), development was performed with an aqueous solution of tetramethylammonium hydroxide to form a pattern, and its characteristics were examined. As a result, 0.15
The line and space of μm could be resolved.

Further, this was used as a cyclohexanone solution, which was then applied onto a quartz wafer to a film thickness of 1 μm, and the transparency to ArF excimer laser light (193 nm) was evaluated. The transmittance was 70%.

[1698] Furthermore, carbon tetrafluoride (CF
₄ ) The etching rate by gas was measured. The dry etching resistance was evaluated under the following conditions.
That is, the flow rate of CF ₄ is 12.6 sccm, the degree of vacuum is 10 mtorr, and the microwave output is 150 W.
And The etching rate was 0.3, which was excellent for PMMA. In this example, the monomer represented by the general formula (2), t-butyl methacrylate (functional group capable of decomposing with acid), and methacrylic acid (alkali-soluble group) are within the hatched area in FIG. It can be set to any composition ratio. (Example III-2) to (Example III-54) Hereinafter, in (Example III-2) to (Example III-54),
The characteristics were examined in the same manner as in Example (III-1) above, except that the copolymers containing the components shown in Tables 332 to 335 were used, respectively. The etching rate is a value for PMMA. Tables 332 to 335 show the monomer components other than t-butyl methacrylate and methacrylic acid in the copolymer, that is, the monomer portion represented by the general formula (2). The polymer was synthesized in the same manner as each synthesis example of the above-mentioned Example I.

[1699]

[Table 332]

[1700]

[Table 333]

[1701]

[Table 334]

[1702]

[Table 335] In each of the examples, a line and space of 0.15 μm could be resolved. (Example III-55)-(Example III-108) Hereinafter, in Example (III-55) -Example (III-108), the menthyl dimethyl obtained by said synthetic example (III-1) is mentioned. Using 0.04 g of sulfonium triflate as a photoacid generator, 2 g of the copolymer shown in Tables 336 to 339 below and 3,3-bis-4′-t-as a dissolution inhibitor.
Butoxycarbonyloxynaphthalenyl-1 (3H) -isobenzofuranone 0.1 g was dissolved in 2-ethoxyethyl acetate 8 mL. The characteristics were examined in the same manner as in Example (III-1). The etching rate is a value for PMMA.

[1703]

[Table 336]

[1704]

[Table 337]

[1705]

[Table 338]

[1706]

[Table 339] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example III-3) Citronellyl dimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of citronellyl mercaptomethane. (Example III-109) to (Example III-162) Except that the citronellyl dimethylsulfonium triflate obtained in the above Synthesis Example (III-3) is used as the photoacid generator, the above-mentioned Example ( III-1) -Example (III-
A chemically amplified resist was obtained in the same manner as 54), and its characteristics were examined in the same manner as described above.

The obtained results are summarized in Tables 340 to 343 below. The etching rate is a value for PMMA.

[1708]

[Table 340]

[1709]

[Table 341]

[1710]

[Table 342]

[1711]

[Table 343] In each of the examples, a line and space of 0.15 μm could be resolved. (Example III-163) to (Example III-216) The above-mentioned Example (except that the citronellyl dimethylsulfonium triflate obtained in the above-mentioned Synthesis Example (III-3) was used as the photo-acid generator. III-55) to Example (III
Chemically amplified resist was obtained in the same manner as in (-108), and its characteristics were examined in the same manner as described above.

The obtained results are summarized in Tables 344 to 347 below. The etching rate is a value for PMMA.

[1713]

[Table 344]

[1714]

[Table 345]

[1715]

[Table 346]

[1716]

[Table 347] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example III-4) Except that menthyl mercaptomethane is replaced with the same amount of pinocamphyl mercaptomethane.
Pincanfillyl dimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) above. (Example III-217) to (Example III-270) The above-mentioned Example except that the pinocamphyl dimethylsulfonium triflate obtained in the above-mentioned Synthesis Example (III-4) is used as the photo-acid generator. (III-1) to Example (III
A chemically amplified resist was obtained in the same manner as in (-54), and its characteristics were examined in the same manner as described above.

The obtained results are summarized in Tables 348 to 351 below. The etching rate is a value for PMMA.

[1718]

[Table 348]

[1719]

[Table 349]

[1720]

[Table 350]

[1721]

[Table 351] In each of the examples, a line and space of 0.15 μm could be resolved. (Example III-271) to (Example III-324) The above-mentioned example except that the pinocanophyll dimethylsulfonium triflate obtained in the above-mentioned synthesis example (III-4) is used as the photoacid generator. (III-55) to Example (I
A chemically amplified resist was obtained in the same manner as in II-108), and its characteristics were examined in the same manner as described above.

The obtained results are summarized in Tables 352 to 355 below. The etching rate is a value for PMMA.

[1723]

[Table 352]

[1724]

[Table 353]

[1725]

[Table 354]

[1726]

[Table 355] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example III-5) Geranyldimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of geranyl mercaptomethane. (Example III-325) to (Example III-378) The above-mentioned Example (III) except that the geranyldimethylsulfonium triflate obtained in the above-mentioned Synthesis Example (III-5) is used as the photoacid generator. -1) to Example (III-5)
A chemically amplified resist was obtained in the same manner as 4), and its characteristics were examined in the same manner as described above.

The obtained results are summarized in Tables 356 to 359 below. The etching rate is a value for PMMA.

[1728]

[Table 356]

[1729]

[Table 357]

[1730]

[Table 358]

[1731]

[Table 359] In each of the examples, a line and space of 0.15 μm could be resolved. (Example III-379) to (Example III-432) The above-mentioned Example (III) except that the geranyldimethylsulfonium triflate obtained in the above-mentioned Synthesis Example (III-5) is used as the photoacid generator. -55) to Example (III-1)
08), a chemically amplified resist was obtained, and its characteristics were examined in the same manner as described above.

The obtained results are summarized in Tables 360 to 363 below. The etching rate is a value for PMMA.

[1733]

[Table 360]

[1734]

[Table 361]

[1735]

[Table 362]

[1736]

[Table 363] In each of the examples, a line and space of 0.15 μm could be resolved. (Synthesis Example III-6) Fentyldimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) above except that menthyl mercaptomethane was replaced with the same amount of fentylcaptomethane. (Example III-433) to (Example III-486) The above-mentioned Example (except that the fentyl dimethylsulfonium triflate obtained in the above-mentioned Synthesis Example (III-6) was used as the photo-acid generator. III-1) to Example (III-5)
A chemically amplified resist was obtained in the same manner as 4), and its characteristics were examined in the same manner as described above.

The obtained results are summarized in Tables 364 to 367 below. The etching rate is a value for PMMA.

[1738]

[Table 364]

[1739]

[Table 365]

[1740]

[Table 366]

[1741]

[Table 367] In each of the examples, a line and space of 0.15 μm could be resolved. (Example III-487) to (Example III-540) The above-mentioned Example (except that the fentyldimethylsulfonium triflate obtained in the above-mentioned Synthesis Example (III-6) was used as a photo-acid generator. III-55) to Example (III-
A chemically amplified resist was obtained in the same manner as in 108), and its characteristics were examined in the same manner as described above.

The obtained results are summarized in Tables 368 to 371 below. The etching rate is a value for PMMA.

[1743]

[Table 368]

[1744]

[Table 369]

[1745]

[Table 370]

[1746]

[Table 371] In each of the examples, a line and space of 0.15 μm could be resolved.

Now, various photo-acid generators will be synthesized and used to prepare the above-mentioned Examples (III-1) to (III).
-54), and Example (III-55) to Example (III-
A chemically amplified resist was synthesized in the same manner as 108).
Transparency of each resist with respect to ArF excimer laser light was examined in the same manner as in Example (III-1), and it was found that the transmittance was 60% to 75% at 193 nm when converted to 1 μm. Further, in each of the examples, a line and space of 0.15 μm could be resolved.

[1748] The synthesis of the photo-acid generator used is shown in the following Synthesis Examples (III-7) to (III-30). (Synthesis Example III-7) Neryldimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) above except that menthyl mercaptomethane was replaced with the same amount of neryl mercaptomethane. (Synthesis Example III-8) Bornyldimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of bornyl mercaptomethane. (Synthesis Example III-9) Cinerymethyldimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of cineryl mercaptomethane. (Synthesis Example III-10) A pinyldimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of pinyl mercaptomethane. (Synthesis Example III-11) Except that menthyl mercaptomethane is replaced with the same amount of ascaridyl mercaptomethane.
Alkali dildimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) above. (Synthesis Example III-12) Except that menthyl mercaptomethane is replaced with the same amount of farnesyl mercaptomethane,
Farnesyl dimethylsulfonium triflate was obtained in the same manner as in the above-mentioned synthesis example (III-1). (Synthesis Example III-13) A patchurildimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of patchuril mercaptomethane. (Synthesis Example III-14) Neroridyldimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of nerolidyl mercaptomethane. (Synthesis Example III-15) Carotyldimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of carotylmercaptomethane. (Synthesis Example III-16) A cazinyldimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of cazinyl mercaptomethane. (Synthesis Example III-17) Lancil dimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) above except that menthyl mercaptomethane was replaced with the same amount of lanyl mercaptomethane. (Synthesis Example III-18) Except that menthyl mercaptomethane is replaced with the same amount of eudesmilmercaptomethane.
Oydesmil dimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) above. (Synthesis Example III-19) A ceryl dimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of ceryl mercaptomethane. (Synthesis Example III-20) Guayyldimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of guayl mercaptomethane. (Synthesis Example III-21) Kessoglycosyl dimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of sessoglycosylmercaptomethane. (Synthesis Example III-22) Phytyldimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of phytyl mercaptomethane. (Synthesis Example III-23) Sucralyldimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of sucralyl mercaptomethane. (Synthesis Example III-24) Manyldimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of manyl mercaptomethane. (Synthesis Example III-25) A hinokyl dimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of hinokyl mercaptomethane. (Synthesis Example III-26) Except that menthyl mercaptomethane was replaced with the same amount of ferguinyl mercaptomethane,
Ferguinyl dimethylsulfonium triflate was obtained in the same manner as in the above Synthesis Example (III-1). (Synthesis Example III-27) Totaryl dimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) above except that menthyl mercaptomethane was replaced with the same amount of totaryl mercaptomethane. (Synthesis Example III-28) Sugyldimethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) except that menthyl mercaptomethane was replaced with the same amount of sugyl mercaptomethane. (Synthesis Example III-29) Dimenthylmethylsulfonium triflate was obtained in the same manner as in Synthesis Example (III-1) above except that menthyl mercaptomethane was replaced with the same amount of menthyl mercaptomenthane. (Synthesis Example III-30) Except that menthyl mercaptomethane is replaced with the same amount of menthyl mercaptomenthane, and iodomethane is replaced with the same amount of menthyl iodide, as in the above Synthesis Example (III-1), Trimenthylmethylsulfonium triflate was obtained.

[1749]

As described above, according to the present invention,
Provided is a photosensitive material which has very little absorption for a single-wavelength light source and has excellent dry etching resistance. In addition to these characteristics, the photosensitive material of the present invention is further characterized by being extremely excellent in heat resistance and adhesion to a substrate. Therefore, by using the photosensitive material of the present invention, it is possible to form a fine pattern having a good shape on the order of quarter micron.

The photosensitive material of the present invention exerts its effect particularly when forming a pattern using KrF excimer laser light or ArF excimer laser light.
It can be sufficiently used also in pattern formation using eepUV light, electron beams, X-rays and the like. Such a photosensitive material has a remarkable effect in the photolithography technology in the manufacturing process of semiconductor devices, and its industrial value is extremely large.

[Brief description of drawings]

FIG. 1 is a diagram showing a composition ratio of a copolymer in a photosensitive material of the present invention.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Reference number within the agency FI Technical display location G03F 7/038 505 7/039 501 H01L 21/027 (72) Inventor Shin Nakase Kawasaki, Kanagawa Prefecture Komukai-Toshiba-cho 1-ku, Toshiba Research & Development Center

Claims (11)

[Claims] 1. A photosensitive material containing a compound having a terpenoid skeleton. 2. The photosensitive material according to claim 1, wherein the terpenoid skeleton contains a compound having a monovalent menthyl group or a menthyl derivative group represented by the following general formula (1). Embedded image (In the general formula (1), R is a hydrogen atom or a monovalent hydrocarbon group. R ¹ may be the same or different from each other, and a hydrogen atom, a halogen atom, a hydrocarbon group,
A hydroxyl group, an alkoxyl group, an amino group, an imide group, an amide group, a sulfonyl group, a carboxyl group, a carbonyl group, and a sulfonamide group, and R ^{1 s} may be bonded to each other to form a ring. ) 3. The compound having a monovalent menthyl group or a menthyl derivative group is a compound represented by the following general formula (2) or a general formula (3) shown below. The photosensitive material according to claim 2, which is a polymer having at least one compound selected from the compounds described above as a monomer, and containing the polymer as a base resin. Embedded image (In the general formula (2), R ³ is an organic group containing a menthyl group or a menthyl derivative group represented by the general formula (1), and R ⁴ is an alkyl group, a carboxyl group, an alkoxycarbonyl group, a halogen atom or It is a hydrogen atom.) (In the general formula (3), R ⁵ and R ⁶ are monovalent organic groups or hydrogen atoms, and at least one of them contains a menthyl group or a menthyl derivative group represented by the general formula (1). .) 4. The photosensitive material according to claim 1, wherein the compound having a terpenoid skeleton contains a group capable of decomposing or crosslinking with an acid, and a photo-acid generator is added to the compound. 5. The base resin is a compound represented by the following general formula (4), which contains a group capable of decomposing or crosslinking with an acid, and a compound represented by the general formula (2) or the above general formula. A copolymer comprising a compound represented by (3) as a monomer, or a polymer comprising a compound represented by the general formula (3) and having a group capable of decomposing or crosslinking with an acid,
The photosensitive material according to claim 3, wherein the base resin contains a photo-acid generator. [Chemical 4] (In the above general formula (4), R ¹³ is a monovalent organic group,
¹⁴ is an alkyl group, a halogen atom or a hydrogen atom. ) 6. The compound having a terpenoid skeleton contains an alkali-soluble group, and a dissolution inhibitor and a photo-acid generator are mixed with the compound.
The photosensitive material as described in 1. 7. The base resin is a compound containing an alkali-soluble group and a compound represented by the general formula (2) or a copolymer containing the compound represented by the general formula (3) as a monomer, Alternatively, it is a polymer having a compound represented by the general formula (3) and containing an alkali-soluble group as a monomer, and a dissolution inhibitor and a photo-acid generator are mixed with the base resin. The photosensitive material as described in 1. 8. The photosensitive material according to claim 4, wherein the photoacid generator is a compound having a naphthalene skeleton. 9. A photosensitive material comprising a compound containing a group capable of decomposing or crosslinking with an acid as a base resin, and a compound having a terpenoid skeleton as a photo-acid generator. 10. A photosensitive material comprising a base resin containing an alkali-soluble group, a dissolution inhibitor, and a compound having a terpenoid skeleton as a photoacid generator. 11. The photosensitive material according to claim 9, wherein the terpenoid skeleton contains a monovalent menthyl group or a menthyl derivative group represented by the following general formula (1). [Chemical 5] (In the general formula (1), R is a hydrogen atom or a monovalent hydrocarbon group. R ¹ may be the same or different from each other, and a hydrogen atom, a halogen atom, a hydrocarbon group,
A hydroxyl group, an alkoxyl group, an amino group, an imide group, an amide group, a sulfonyl group, a carboxyl group, a carbonyl group, and a sulfonamide group, and R ^{1 s} may be bonded to each other to form a ring. )