JP2001005190A - Pattern forming material and pattern forming method using the same - Google Patents

Abstract

[PROBLEMS] To improve the exposure latitude of a negative pattern forming material,
As a result, the precision of the fine processing is improved, and a high-resolution pattern appears. A pattern latent image forming portion formed by irradiation with radiation is changed in solubility in an alkaline aqueous solution,
When all of the coating film in the non-irradiated portion is dissolved by performing the developing treatment, the residual film ratio of the radiation-irradiated portion becomes 70% of the coating film thickness.
% Or more, and the residual film ratio when the residual film is immersed in a 50% methanol aqueous solution is 50% or more.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a pattern forming material and a pattern forming method used for microfabrication of a semiconductor device or the like. Generated
The present invention relates to a negative pattern forming material that reduces the solubility of the irradiated portion in an aqueous alkali solution by a reaction using an acid as a catalyst and makes a pattern appear in a step of using the aqueous alkali solution as a developer.

[0002]

2. Description of the Related Art An acid is generated in a pattern latent image forming portion by irradiation of a pattern such as an electron beam or an ultraviolet ray, and the solubility of the irradiated portion in a developing solution is changed by a reaction using the acid as a catalyst. With respect to a pattern forming material which causes a negative pattern to appear, and a pattern forming method using the same, those described in US Pat. No. 4,800,152, JP-A-62-164045, JP-A-2-217855 and the like are known. These prior arts describe an acid precursor that generates an acid upon irradiation with radiation, and a negative-type pattern forming material having a mechanism of forming a pattern by crosslinking under an acid catalyst to reduce solubility in an aqueous alkali solution. Have been.

The solubility of a negative pattern forming material (hereinafter referred to as a cross-linking pattern forming material) utilizing an acid-catalyzed cross-linking reaction as described in the prior art described above in an aqueous alkali solution changes due to an increase in molecular weight due to the cross-linking reaction.
However, these cross-linking pattern forming materials have problems such as a large irradiation dose of radiation required for pattern formation, a large change in sensitivity to a change in heat treatment temperature after irradiation, and low storage stability.

Japanese Patent Application Laid-Open No. 290917/1990 discloses a negative pattern forming material (hereinafter referred to as a polarity conversion pattern forming material) whose solubility in an aqueous alkali solution is based not on a crosslinking reaction but on a polarity conversion reaction of a secondary or tertiary alcohol. JP-A-4-165359 and JP-A-7-104473 are known. These polarity conversion pattern forming materials are characterized by high sensitivity, high resolution, and excellent dimensional accuracy and stability, as compared with crosslinked pattern forming materials. However, in the formation of a pattern using the polarity conversion pattern forming material, the problem that the pattern shape deteriorates as the development time with alkali becomes longer, and the resolution deteriorates, became apparent. Such dependence on the development time causes a significant decrease in exposure latitude when forming a pattern using radiation having a deteriorated irradiation profile.

[0005]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a high-precision negative-type pattern forming material which has no development time dependency and has an improved exposure latitude, and a high-resolution pattern forming method using the same. Is to do.

[0006]

An object of the present invention is to provide an alkali-soluble polymer, an acid precursor that generates an acid upon irradiation with radiation, at least one primary alcohol having a hydroxyl group on carbon directly bonded to an aromatic ring, A pattern forming material comprising at least one tertiary alcohol having a hydroxyl group on carbon directly bonded to an aromatic ring, forming a coating film made of the above pattern forming material, and using an electron beam, ultraviolet or other radiation to form the coating film. After forming a predetermined pattern latent image on the coating film and promoting a reaction to change the solubility of the pattern latent image forming portion in an aqueous alkali solution, a developing process using an aqueous alkali solution is performed to remove all the coating film in the unirradiated portion. When dissolved, the residual film ratio of the radiation-irradiated portion is 70% or more of the applied film thickness, and when the residual film is immersed in a 50% aqueous methanol solution Residual film ratio can be achieved by the pattern forming method using the pattern forming material and which is characterized in that 50% or more.

The primary alcohol having a hydroxyl group on carbon directly bonded to the aromatic ring of the present invention is preferably at least one compound selected from the group represented by the following chemical formulas 1 to 13.

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(Wherein R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. R 2 to R 6 represent hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, Represents an atom or an atomic group selected from a substituted or unsubstituted alkoxy group, a hydroxyl group, a phenyl group, a methoxy group, and a cyclopropyl group, wherein R2 to R6 may be the same or different. Examples of the primary alcohol having a hydroxyl group on carbon directly bonded to an aromatic ring used in the present invention include benzyl alcohol, m-xylene glycol, p-xylene glycol, 1,3,5-benzenetrimethanol, 2-hydroxy-5 -Methyl-1,3-benzenedimethanol, 3,5,3 ', 5'-hexahydroxymethyl-
4,4'-dihydroxydiphenyl, bis (3 ', 5'
-Dihydroxymethyl-4'-hydroxyphenyl) methylene, 2,2-bis (3 ', 5'-dihydroxymethyl-4'-hydroxyphenyl) propane, 1,4-bis (2- (3', 5'- Dihydroxymethyl-4'-hydroxyphenyl) propane) benzene and the like.

The tertiary alcohol having a hydroxyl group on carbon directly bonded to the aromatic ring of the present invention is preferably at least one compound selected from the group represented by the following chemical formulas 14 to 28.

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(Wherein R1 or R2 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. R3 to R6 represent hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. 4 substituted or unsubstituted alkoxy groups,
Represents an atom or atomic group selected from a hydroxyl group, a phenyl group, a methoxy group, and a cyclopropyl group. R
3-R6 may be the same or different. Examples of the tertiary alcohol having a hydroxyl group on carbon directly bonded to an aromatic ring used in the present invention include 1,3-bis (2-hydroxy-2-propyl) benzene and 1,3
-Bis (3-hydroxy-3-pentyl) benzene,
1,3-bis (2-hydroxy-2-propyl) -5
Methoxybenzene, 5-chloro-1,3-bis (2-hydroxy-2-propyl) benzene, 5-bromo-1,
3-bis (2-hydroxy-2-propyl) benzene,
1,4-bis (2-hydroxy-2-propyl) benzene, 1,4-bis (3-hydroxy-3-pentyl) benzene, 1,4-bis (2-hydroxy-2-propyl) -2,3 , 5,6-tetramethylbenzene, 2-chloro-1,4-bis (2-hydroxy-2-propyl)
Benzene, 2-bromo-1,4-bis (2-hydroxy-2-propyl) benzene, 1,3,5-tris (2-
(Hydroxy-2-propyl) benzene, 1,3,5-tris (3-hydroxy-3-pentyl) benzene,
5-bis (2-hydroxy-2-propyl) naphthalene, 1,4-bis (2-hydroxy-2-propyl) naphthalene, 9,10-bis (2-hydroxy-2-propyl) anthracene, and the like. .

Among the tertiary alcohols used in the pattern forming material of the present invention, tertiary alcohols having three or more 2-hydroxyisopropyl groups on the same aromatic ring have the lowest reaction among alcohols in combination with primary alcohols. It is more preferable as the pattern forming material of the present invention.

Preferred alkali-soluble resins in the present invention include novolak resin, m, p-cresol novolak resin, halogenated novolak resin, polyhydroxystyrene, and a resin in which a part of the phenolic hydroxyl group of polyhydroxystyrene is protected. Including mixed resin,
Examples include high molecular compounds such as halogenated polyhydroxystyrene, humanoxystyrene / styrene copolymer, and polymethylglutarimide. Among them, polyhydroxystyrene is more preferable as the alkali-soluble resin used in the pattern forming material of the present invention, and particularly, those having a weight average molecular weight in the range of 1,000 to 5,000 are more preferable.

As the acid precursor used in the present invention, an onium salt such as a triarylsulfonium salt, a naphthoylmethyltetramethylenesulfonium salt or a diaryliodonium salt can be used. The counter anion of the onium salt is trifluoromethanesulfonic acid, trifluoroacetic acid,
An alkylsulfonic acid such as methanesulfonic acid, an arylsulfonic acid such as toluenesulfonic acid, a Lewis acid such as tetrafluoroboronic acid, hexafluoroantimonic acid, and hexafluoroarsenic acid are used. In addition, alkyl and aryl sulfonic acid esters described in JP-A-2-245756 can also be used as the acid precursor.

The pattern forming material of the present invention can be used in combination with a basic compound and an organic salt. Examples of the basic compound applicable to the present invention include aniline, benzylamine, tyramine, 2-aminoquinoline, 3-aminodiphenyl, 4-aminophenol,
5-aminoindane, 5-aminoindazole, cyclohexylamine, diphenylamine, dicyclohexylamine, 2,2-dipyridylamine, tri-n-methylamine, triphenylamine, pyridine, 2-picoline, 2,6-lutidine, 6- Amino-2,4-lutidine, 2,4-diaminopyridine, 2-benzylpyridine, 3-benzylpyridine, 4-benzylpyridine,
-Phenylpyridine, 2,6-di-p-tolylpyridine, amelin, benzoguanamine, N (2), N (2)
-Diallylmelamine, aminomelamine, hexa (methoxymethyl) melamine, quinoline, 2,2-biquinoline,
4-amino-2-methylquinoline, 2,4-dimethylquinoline, 4,4-diphenyl-2,2-dipyridyl,
Examples thereof include 2,2-bi-4-picoline, 1,3-di (4-pyridyl) propane, and 1,2-di (2-pyridyl) ethylene.

Examples of the organic salt include tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide, tetramethylammonium trifluoromethanesulfonate, tetramethylammonium paratoluenesulfonate, triethylbenzylammonium chloride, triethylbenzylammonium bromide, Triethylbenzylammonium iodide, tetrabutylammonium trifluoromethanesulfonate, tetra-n-butylammonium perchlorate, trimethylsulfonium chloride,
Trimethylsulfonium bromide, trimethylsulfonium iodide, tetraethylphosphonium chloride, tetraethylphosphonium bromide, tetraethylphosphonium iodide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, tetraphenylphosphonium iodide, methyltriphenylphosphonium chloride, methyltriphenylphosphonium bromide, Methyltriphenylphosphonium iodide, tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tetra-n-amylammonium chloride, tetra-n-amylammonium bromide, tetra-n-amylammonium iodide, tetraethylsulfo Xonium iodide, pyridinium paratoluenesulfone , N- fluoro pyridinium trifluoromethane sulfonate, and the like.

In the pattern-forming material of the present invention, an alkali-soluble polymer, an acid precursor which generates an acid upon irradiation, a primary alcohol having a hydroxyl group on carbon directly bonded to an aromatic ring, and a direct alcohol bonded to an aromatic ring The composition ratio of the tertiary alcohol having a hydroxyl group on carbon is 100
Parts by weight, 0.1-30 parts by weight, 5-40 parts by weight, 5-4
It is desirably in the range of 0 parts by weight. If the total amount of alcohol is larger than this range, phase separation is likely to occur, so that it is difficult to form a uniform coating film. If the total amount is small, the insolubilization of the coating film does not sufficiently proceed. On the other hand, if the amount of the acid generator is larger than this range, the development time is prolonged, and if it is smaller, sufficient sensitivity cannot be obtained.

FIG. 1 shows the change of the normalized film thickness with respect to the irradiation dose measured using the conventional negative pattern forming material and the pattern forming material of the present invention.

The residual film ratio after alkali development of both the conventional negative pattern forming material and the pattern formed by using the pattern forming material of the present invention is 90% or more.
The residual film ratio after immersion in the aqueous methanol solution is 50% or less for the conventional negative pattern forming material, and 80% or more for the pattern forming material of the present invention. The sensitivity and contrast of the pattern forming material of the present invention are not changed by immersion in a 50% aqueous methanol solution. Thus, when the pattern forming material of the present invention is used, the development time dependency is improved, and a pattern with high exposure latitude can be formed. That is, the use of the pattern forming material of the present invention enables high-precision microfabrication and provides a highly practical pattern.

When a negative pattern is formed by using the pattern forming material of the present invention, in order to transfer an effective pattern by a process such as etching, a coating film is defined as a residual film ratio of the irradiated portion after development. It is desirable to secure 70% or more of the thickness. That is, when the remaining film thickness after development is at least 70% or more of the film thickness before development, for example, when the resist film is shaved in the subsequent processing, the intended pattern transfer may not be realized.

Also, the 50% methanol aqueous solution immersion treatment is a treatment that makes it easy to distinguish the pattern resistance during normal alkaline development for a long period of time by development under severe conditions. If the composition is such that the above-mentioned remaining resist film can be formed, it is possible to confirm that a change in the remaining film ratio after a long period of normal alkali development has been suppressed and a stable resist pattern has been formed.

[0049]

(Example 1) Weight average molecular weight 5,
000 polyhydroxystyrene: 100 parts by weight, diphenyliodonium triflate: 20 parts by weight, 1,3
-Bis (2-hydroxy-2-propyl) benzene: 2
0 parts by weight, 1,3,5-benzenetrimethanol: 15
0.1 part by weight of 2,6 l-tidine was dissolved in propylene glycol monomethyl ether. this,
After filtration through a membrane filter with a pore size of 0.1 μm,
It was stored for one month in a clean room at 4 ° C. When the sensitivity and development time before and after storage were measured, no change was observed.
It showed good storage stability.

Next, the above-mentioned pattern forming material is spin-coated on a silicon wafer and heat-treated at 100 ° C. for 2 minutes.
A coating film of 0.4 μm was obtained. This coating film was irradiated with a pattern using a KrF excimer laser stepper,
Heat treatment for 2.3 minutes
Development processing was performed for 20 seconds with an 8% aqueous solution. as a result,
0.3μm line and space repetition pattern,
It was formed at an exposure amount of 15.0 mJ / cm ² . The pattern dimensional variation in the repetitive pattern of 0.5 μm line and space of this pattern forming material is 0.02 μm.
/ ° C or lower. (Here, the pattern dimension variation indicates the variation of the pattern dimension when the temperature of the heat treatment after exposure changes by 1 ° C. from the set temperature).

The residual film ratio of the pattern formed by the pattern forming material of the example after alkali development was 94%, and the residual film ratio after immersion in a 50% aqueous solution of methanol was 82%. Further, according to the pattern forming method using the pattern forming material of the embodiment, a high-resolution pattern can be formed with high dimensional accuracy by an exposure method using a KrF excimer laser projection exposure apparatus. Is advantageous.

Example 2 100 parts by weight of polyhydroxystyrene having a weight average molecular weight of 5,000, 15 parts by weight of diphenyliodonium triflate, 20 parts by weight of 1,3-bis (2-hydroxy-2-propyl) benzene Part, 2,2-bis (3 ′, 5′-dihydroxymethyl-
10 parts by weight of 4'-hydroxyphenyl) methylene and 0.1 parts by weight of benzylamine were dissolved in propylene glycol monomethyl ether. This has a pore diameter of 0.1μ.
m, filtered on a silicon wafer, spin-coated on a silicon wafer, and heat-treated at 100 ° C. for 2 minutes.
A μm coating film was obtained. The coating film was irradiated with light using an i-line reduction projection exposure apparatus using a phase shift mask, and then heat-treated at 70 ° C. for 2 minutes to obtain 2.38 tetramethylammonium hydroxide.
% Aqueous solution for 30 seconds. As a result, 0.
A 35 μm line and space repeating pattern was formed at an exposure dose of 250 mJ / cm ² . The pattern dimensional variation in the repetitive pattern of 0.5 μm line and space of this pattern forming material is 0.02 μm / ° C.
It was below.

The residual film ratio of the pattern formed using the pattern forming material of the example after alkali development was 90%, and the residual film ratio after immersion in a 50% aqueous solution of methanol was 80%. According to the pattern forming method using the pattern forming material of the present embodiment, a high-resolution pattern can be formed with high dimensional accuracy by an exposure method using a combination of an i-line reduction projection exposure apparatus and a phase shift mask. It is economically advantageous.

Example 3 Polyhydroxystyrene having a weight average molecular weight of 5,000: 100 parts by weight, diphenyliodonium triflate: 15 parts by weight, 1,3,5-tris (2-hydroxy-2-propyl) benzene: Fifteen
15 parts by weight of 3,5,3 ', 5'-hexahydroxymethyl-4,4'-hydroxydiphenyl and 0.1 part by weight of phenylpyridine were dissolved in propylene glycol monomethyl ether. This has a pore diameter of 0.1 μm
And stored in a clean room at 24 ° C. for one month. When the sensitivity and development time before and after storage were measured, no change was observed, and good storage stability was exhibited.

Next, the above-mentioned pattern forming material is spin-coated on a silicon wafer and heat-treated at 100 ° C. for 2 minutes.
A coating film of 0.35 μm was obtained. After irradiating the coating film with an electron beam using an electron beam lithography apparatus (acceleration voltage 50 kV), 75
The resultant was subjected to a heat treatment for 2 minutes at a temperature of 2.degree. As a result, a 0.3 μm line and space repeating pattern was formed at an electron beam irradiation amount of 8 μC / cm ² . The pattern dimensional variation in the repetitive pattern of 0.5 μm line and space of this pattern forming material was 0.02.
μm / ° C. or less. The residual film ratio of the pattern formed using the pattern forming material of the example after alkali development was 95%.
The residual film ratio after immersion in a 50% aqueous solution of methanol was 86%.

According to the pattern forming method using the pattern forming material of this embodiment, it is possible to form a high-resolution pattern with high dimensional accuracy by a pattern forming method using an electron beam irradiation apparatus, which is industrially advantageous. It is.

Example 4 Polyhydroxystyrene having a weight average molecular weight of 5,000: 100 parts by weight, diphenyliodonium triflate: 15 parts by weight, 1,3,5-tris (2-hydroxy-2-propyl) benzene: 20
Parts by weight, 2,2-bis (3 ', 5'-dihydroxymethyl-4'-hydroxyphenyl) propane: 10 parts by weight, and 0.15 parts by weight of 2-benzylpyridine were dissolved in propylene glycol monopropyl ether. This was filtered through a membrane filter having a pore size of 0.1 μm, and then stored in a clean room at 24 ° C. for one month. When the sensitivity and development time before and after storage were measured, no change was observed, and good storage stability was exhibited.

Next, the above-mentioned pattern forming material is spin-coated on a silicon wafer and heat-treated at 100 ° C. for 2 minutes.
A coating film of 0.35 μm was obtained. After irradiating the coating film with an electron beam using an electron beam lithography apparatus (acceleration voltage 50 kV), 75
The film was subjected to a heat treatment for 2 minutes at a temperature of 2.degree. As a result, a 0.3 μm line and space repetition pattern was formed at an electron beam irradiation dose of 9 μC / cm ² . The pattern dimensional variation of the pattern forming material in the repeated pattern of 0.5 μm line and space was 0.02.
μm / ° C. or less.

The residual film ratio of the pattern formed by the pattern forming material of the example after alkali development was 94%, and the residual film ratio after immersion in a 50% aqueous solution of methanol was 82%. According to the pattern forming method using the pattern forming material of this embodiment, a pattern with high dimensional accuracy and high resolution can be formed by a pattern forming method using an electron beam irradiation apparatus, which is industrially advantageous.

Example 5 100 parts by weight of polyhydroxystyrene having a weight average molecular weight of 5,000, 15 parts by weight of diphenyliodonium triflate, 20 parts by weight of 1,3-bis (2-hydroxy-2-propyl) benzene Part, 2,2-bis (3 ′, 5′-dihydroxymethyl-
4'-hydroxyphenyl) propane: 10 parts by weight, tetraethylammonium paratoluenesulfonate:
0.5 parts by weight was dissolved in propylene glycol monomethyl ether. This was filtered through a membrane filter with a pore size of 0.1 μm, and then placed in a clean room at 24 ° C.
Saved for months. When the sensitivity and development time before and after storage were measured, no change was observed, and good storage stability was exhibited.

Next, the above pattern forming material is spin-coated on a silicon wafer and heat-treated at 80 ° C. for 2 minutes.
A coating film of 5 μm was obtained. This coating film was irradiated with a pattern using a KrF excimer laser stepper, and then heat-treated at 80 ° C. for 2 minutes to give 2.38% of tetramethylammonium hydroxide.
Development processing was performed for 40 seconds with the aqueous solution. As a result, 0.3
A repeating pattern of μm lines and spaces was formed at an exposure dose of 20 mJ / cm ² . The pattern dimensional variation of the pattern forming material in the repetitive pattern of 0.5 μm line and space was 0.025 μm / ° C. or less.

The residual film ratio of the pattern formed using the pattern forming material of the example after alkali development was 90%, and the residual film ratio after immersion in a 50% aqueous solution of methanol was 80%. According to the pattern forming method using the pattern forming material of the embodiment, an exposure method using a KrF excimer laser projection exposure apparatus can form a high-resolution pattern with high dimensional accuracy, which is industrially advantageous.

(Embodiment 6) FIG. 2 shows a description of a pattern forming method using the pattern forming material of the present invention. As shown in FIG. 2A, a tungsten film is formed on a semiconductor substrate, and a resist film is formed thereon. As shown in (b), radiation is irradiated through a mask, and a resist pattern is obtained by alkali development treatment (c). Dry etching was performed through this pattern (d), and thereafter the resist film was removed by ashing to obtain a wiring pattern (e).

[0064]

By using the pattern forming material of the present invention,
This makes it possible to form a pattern with a high exposure latitude and improve the dimensional accuracy when manufacturing an integrated circuit, which is industrially advantageous.

[Brief description of the drawings]

FIG. 1 is a measurement diagram of a normalized film thickness of a pattern forming material according to a conventional example and an example of the present invention.

FIG. 2 is a sectional view showing a pattern forming method according to an embodiment of the present invention.

[Explanation of symbols]

DESCRIPTION OF SYMBOLS 1 ... Semiconductor substrate, 2 ... Tungsten film, 3 ... Resist film, 4 ... Mask, 5 ... Radiation, 6 ... Latent image.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Tadashi Uchino 1-280 Higashi Koikekubo, Kokubunji-shi, Tokyo Inside the Central Research Laboratory, Hitachi, Ltd. F-term in the Central Research Laboratory (Reference) 2H025 AA01 AA02 AB16 AC01 AC06 AD01 BE00 BJ00 CB42 CC17 CC20 FA12 FA17 2H096 AA27 BA06 EA02 EA06 FA01 GA08

Claims (5)

[Claims] 1. An alkali-soluble polymer, an acid precursor that generates an acid upon irradiation with radiation, at least one primary alcohol having a hydroxyl group on carbon directly bonded to an aromatic ring, and a carbon atom directly bonded to an aromatic ring. A pattern forming material comprising at least one tertiary alcohol having a hydroxyl group, forming a coating film made of the above pattern forming material, and forming a predetermined pattern latent image on the coating film using radiation such as electron beam or ultraviolet ray. After promoting a reaction to change the solubility of the pattern latent image forming portion in the aqueous alkali solution, the developing process using the aqueous alkali solution dissolves all the unirradiated portion of the coating film, and then the irradiation portion Is 70% or more of the coating film thickness, and the remaining film ratio when the remaining film is immersed in a 50% methanol aqueous solution is 50% or more. Pattern forming material according to claim. 2. The pattern forming material according to claim 1, wherein the primary alcohol having a hydroxyl group on carbon directly bonded to an aromatic ring is at least one selected from the group represented by the following chemical formulas 1 to 13. A pattern forming material characterized by using two compounds. Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image (Where R1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. R2 to R6 represent hydrogen, halogen, 1 to 4 carbon atoms)
Represents an atom or an atomic group selected from 4 substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 4 carbon atoms, hydroxyl group, phenyl group, methoxy group, and cyclopropyl group. R2 to R6 may be the same or different. ) 3. The pattern forming material according to claim 1, wherein the tertiary alcohol having a hydroxyl group on carbon directly bonded to an aromatic ring is selected from the group represented by the following chemical formulas 14 to 28. A pattern forming material characterized by using at least one compound. Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image Embedded image (Where R1 or R2 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. R3 to R6 represent hydrogen, halogen,
A substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, 1 carbon atom
Represents an atom or an atomic group selected from substituted to unsubstituted alkoxy groups, hydroxyl groups, phenyl groups, methoxy groups, and cyclopropyl groups. R3 to R6 may be the same or different. ) 4. The pattern-forming material according to claim 1, wherein the alkali-soluble polymer, an acid precursor that generates an acid upon irradiation with radiation, and a direct bond to an aromatic ring as a dissolution-inhibiting precursor. The primary alcohol having a hydroxyl group on carbon, the tertiary alcohol having a hydroxyl group on carbon directly bonded to an aromatic ring has a composition ratio of 100 parts by weight,
The pattern forming material is in a range of 0.1 to 30 parts by weight, 5 to 40 parts by weight, 5 to 40 parts by weight. 5. A step of forming a coating film made of the pattern forming material according to claim 1, and a step of forming a predetermined pattern latent image on the coating film by using radiation such as an electron beam or ultraviolet rays. Forming a pattern, a step of promoting a reaction to change the solubility of the pattern latent image forming portion in an alkaline aqueous solution, and a step of developing the predetermined pattern using the alkaline aqueous solution as a developing solution. Forming method.