KR101566532B1 - Cyanuric acid derivatives and composition for resist underlayer including the cyanuric acid derivatives and method of forming patterns using the composition - Google Patents

Abstract

상기 화학식 1에서, R¹　내지 R³　및 L¹　내지 L⁶는 명세서에서 정의한 바와 같다.A composition for a resist underlayer film comprising the cyanuric acid derivative, and a pattern forming method using the composition.
[Chemical Formula 1]

In Formula 1, R ¹ to R ³ and L ¹ to L ⁶ are as defined in the specification.

Description

TECHNICAL FIELD The present invention relates to a cyanuric acid derivative, a cyanuric acid derivative, a composition for a resist underlayer film including the cyanuric acid derivative, and a pattern formation method using the composition for a resist underlayer film. BACKGROUND ART }

A cyanuric acid derivative, a composition for a resist underlayer film including the cyanuric acid derivative, and a method for forming a pattern using the composition for a resist underlayer film.

There is a need to reduce the size of patterns in industries, including the fabrication of microelectronics as well as micro-scopic structures (e.g., micromachines, magnetoresist heads, etc.) to provide larger amounts of circuitry at a given chip size .

Effective lithographic techniques are essential to reduce pattern size. Lithography affects the fabrication of micro-scopic structures in terms of direct imaging of the pattern on a given substrate as well as in the fabrication of masks typically used for such imaging.

A typical lithographic process involves patterning a radiation-sensitive resist patterning the imaging radiation to form a patterned resist layer. Then, the exposed resist layer is developed with a developing solution. The pattern is then transferred to the backing material by etching the material in the openings of the patterned resist layer. After the transfer is completed, the remaining resist layer is removed.

However, for some lithographic imaging processes, the resist used does not provide sufficient resistance to subsequent etching steps to such an extent that it is possible to effectively transfer the desired pattern to the layer underlying the resist.

Therefore, for example, when an ultra thin film resist layer is required, when a back surface material to be etched is thick, a considerable etching depth is required and / or when it is necessary to use a specific etchant for a predetermined back surface material, Called 　 Layer is used as the intermediate layer between the resist layer and the material layer that can be patterned by transfer from the patterned resist.

The resist underlayer film may be formed using a composition for a resist underlayer film which has high etching selectivity, is resistant to multiple etching, and can minimize reflection between the resist layer and the material layer.

The composition for a resist underlayer film is important in determining the resolution of the resist layer, the rate of lithography, and the exposure characteristics such as residue. This exposure characteristic is particularly important when a microfabrication lithography process is performed using an extreme ultraviolet radiation (EUV) laser.

One embodiment provides a cyanuric acid derivative for use in a resist underlayer film.

Another embodiment provides a composition for a resist underlayer film comprising the cyanuric acid derivative.

Another embodiment provides a method of forming a pattern using the composition for a resist underlayer film.

According to one embodiment, there is provided a cyanuric acid derivative represented by Formula 1 below.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ³ are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 aryl group, C30 cycloalkenyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C20 aldehyde group, a substituted or unsubstituted amino group, a halogen group, a halogen-containing group, ego,

Each of L ¹ to L ⁶ independently represents a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, A substituted or unsubstituted C7 to C20 arylalkylene group, a substituted or unsubstituted C1 to C20 heteroalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C3 to C30 cycloalkenylene group, a substituted or unsubstituted C7 to C20 arylalkylene group, A substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof.

In Formula 1, at least one of R ¹ to R ³ may be a heterocycloalkyl group or a heteroaryl group containing at least one of nitrogen (N), sulfur (S), oxygen (O), and phosphorus (P).

In Formula 1, at least one of R ¹ to R ³ may be selected from the following Formula a, Formula b, or combinations thereof.

(A)

[Formula b]

In the above formula (a) or (b)

R ⁴ to R ¹² each independently represent hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 aryl group, C30 cycloalkenyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C20 aldehyde group, a substituted or unsubstituted amino group, a halogen group, a halogen-containing group, ego,

* Indicates a linking portion with sulfur (S) of formula (1).

The cyanuric acid derivative may be represented by at least one of the following general formulas (1a) and (1b).

[Formula 1a]

[Chemical Formula 1b]

According to another embodiment, there is provided a composition for a resist underlayer film comprising the above-mentioned cyanuric acid derivative, a photosensitive polymer, and a solvent.

The cyanuric acid derivative and the photosensitive polymer were added to 100 parts by weight of the solvent 　 each 　 About 0.1 to 5 parts by weight, and about 0.1 to 30 parts by weight.

According to another embodiment, there is provided a method for manufacturing a resist, comprising the steps of: providing a material layer on a substrate; applying the above-mentioned composition for a resist underlayer film on the material layer; heat treating the composition for a resist underlayer film to form a resist underlayer film; Forming a resist pattern on the resist layer; exposing and developing the resist layer to form a resist pattern; selectively removing the resist underlayer film using the resist pattern and exposing a part of the material layer; And etching the exposed portion of the layer.

The step of forming the resist underlayer film may be performed by a spin-on coating method.

The film density, the solvent elution property and the exposure property can be improved.

Hereinafter, exemplary embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

Unless otherwise defined herein, 'substituted' means that a hydrogen atom in the compound is a halogen atom (F, Br, Cl or I), a hydroxy group, an alkoxy group, a nitro group, a cyano group, an amino group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, C6 to C30 arylalkyl groups, C7 to C30 arylalkyl groups, C1 to C4 alkoxy groups, C1 to C20 heteroalkyl groups, C3 to C20 heteroarylalkyl groups, C3 to C30 cycloalkyl groups, C3 to C15 cycloalkenyl groups, C6 to C30 heteroaryl groups, C15 cycloalkynyl group, a C2 to C20 heterocycloalkyl group, and combinations thereof.

In addition, unless otherwise defined herein, "hetero" means containing 1 to 3 heteroatoms selected from N, O, S and P.

The cyanuric acid derivative according to one embodiment may be represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ¹ to R ³ are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 aryl group, C30 cycloalkenyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C20 aldehyde group, a substituted or unsubstituted amino group, a halogen group, a halogen-containing group, to be.

At least one of R ¹ to R ³ may be a heterocycloalkyl group or a heteroaryl group containing at least one of nitrogen (N), sulfur (S), oxygen (O) and phosphorus (P)

For example, at least one of R ¹ to R ³ may be selected from the following formula a, formula b, or combinations thereof.

(A)

[Formula b]

In the above formula (a) or (b)

R ⁴ to R ¹² each independently represent hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 aryl group, C30 cycloalkenyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C20 aldehyde group, a substituted or unsubstituted amino group, a halogen group, a halogen-containing group, ego,

* Indicates a linking portion with sulfur (S) of formula (1).

Thus, by introducing a heterocycloalkyl group or a heteroaryl group containing at least one of nitrogen (N), sulfur (S), oxygen (O) and phosphorus (P) into the cyanuric acid derivative, the film density of the resist underlayer film is increased, Can speed up.

Each of L ¹ to L ⁶ is a linking group and each independently represents a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, Or a substituted or unsubstituted C3 to C30 cycloalkenylene group, a substituted or unsubstituted C7 to C20 arylalkylene group, a substituted or unsubstituted C1 to C20 heteroalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, Or an unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof.

The composition for a resist underlayer film according to another embodiment includes the above-mentioned cyanuric acid derivative, a photosensitive polymer, and a solvent.

The photosensitive polymer is not particularly limited as long as it is a compound that causes a chemical reaction by light, and examples thereof include (meth) acrylic polymer, ester polymer, styrene polymer, novolak polymer or blending polymers thereof.

The photosensitive polymer may have a weight average molecular weight of about 2,000 to 100,000, and preferably about 4,000 to 15,000. When the weight average molecular weight of the photosensitive polymer is in the above range, solubility in the solvent is improved.

As described above, in this embodiment, the cyanuric acid derivative and the photosensitive polymer are included as a component of the composition for a resist underlayer film, and the cyanuric acid derivative and the photosensitive derivative are not chemically bonded to each other. When the cyanuric acid derivative is in the form of a single molecule, its molecular weight can be easily controlled. When the cyanuric acid derivative is cross-linked with the photosensitive polymer in the form of a single molecule, the size of the cyanuric acid derivative is small and constant.

The solvent is not particularly limited as long as it has sufficient solubility or dispersibility to the cyanuric acid derivative and the photosensitive polymer, and examples thereof include propylene glycol, propylene glycol diacetate, methoxypropanediol, diethylene glycol, diethylene glycol butyl ether (Ethylene glycol) monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone (or ananone), ethyl lactate, gamma-butyrolactone and acetyl acetone. can do.

The cyanuric acid derivative may be included in an amount of about 0.1 to 5 parts by weight based on 100 parts by weight of the solvent. Within the above range, the cyanuric acid derivative is preferably included in an amount of about 0.25 to 2.5 parts by weight based on 100 parts by weight of the solvent. By incorporating the above-mentioned cyanuric acid derivative in the above range, unnecessary particles are not formed in the spin-on coating, and the crosslinking power with the photosensitive polymer is optimized.

The photosensitive polymer may be included in an amount of about 0.1 to 30 parts by weight based on 100 parts by weight of the solvent. Within the above range, the photosensitive polymer may be added to 100 parts by weight of the solvent 　 Preferably about 0.5 to 10 parts by weight. By including the photosensitive polymer within the above range, the thickness of the resist underlayer film can be controlled to a desired thickness.

The composition for a resist underlayer film can increase the film density by including the cyanuric acid derivative, thereby preventing contaminants from entering the substrate or the lower film. In addition, by controlling the polarity of the composition for a lower resist film by the above-mentioned cyanuric acid derivative, resist residues remaining on the resist lower layer film after the exposure and / or the developing process are reduced, and resolution, line-width roughness line-width roughness (LWR), and development residue.

The composition for a resist underlayer film may further include at least one additive selected from a surfactant, an acid catalyst, and a crosslinking agent.

The surfactant may be, for example, an alkylbenzenesulfonate, an alkylpyridinium salt, a polyethylene glycol, or a quaternary ammonium salt, but is not limited thereto.

The acid catalyst is preferably a thermally activated acid catalyst.

As the acid catalyst, an organic acid such as p-toluenesulfonic acid monohydrate may be used, and a thermal acid generator (TAG) for improving storage stability may be used. The thermal acid generator is an acid generator which releases acid upon heat treatment, and examples thereof include pyridinium p-toluenesulfonate, 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl Tosylate, alkyl esters of organic sulfonic acids, and the like.

The crosslinking agent is an amino resin such as an etherified amino resin, which is capable of crosslinking the repeating unit of the polymer by heating. A glycoluril compound such as a compound represented by the following formula (A); A bis epoxy compound such as a compound represented by the following formula (B); A melamine or a derivative thereof such as N-methoxymethylmelamine, N-butoxymethylmelamine or a melamine derivative represented by the following formula (C); Or a mixture thereof.

(A)

[Chemical Formula B]

≪ RTI ID = 0.0 &

The surfactant, the acid catalyst and the crosslinking agent may be contained in an amount of about 0.001 to 3 parts by weight based on 100 parts by weight of the composition for a resist underlayer film. By including it in the above range, solubility and crosslinkability can be ensured without changing the optical properties of the resist underlayer film.

The composition for a resist underlayer film is not dissolved in a resist solvent and / or a developer for forming a resist and is not mixed with a resist solution for forming a resist, so that the composition can be chemically stable during the process.

Hereinafter, a method of forming a pattern using the composition for a resist underlayer film will be described.

The method for forming a pattern according to an embodiment includes the steps of providing a material layer on a substrate, applying a composition for a resist underlayer film including the above-described cyanuric acid derivative, a photosensitive polymer and a solvent on the material layer, Forming a resist underlayer film on the resist underlayer film, forming a resist layer on the under resist film layer, exposing and developing the resist layer to form a resist pattern, selectively removing the resist underlayer film using the resist pattern, And exposing a portion of the material layer, and etching the exposed portion of the material layer.

The substrate may be, for example, a silicon wafer, a glass substrate, or a polymer substrate.

The material layer is a material to be finally patterned and may be a metal layer such as aluminum, copper, or the like, a semiconductor layer such as silicon, or an insulating layer such as silicon oxide, silicon nitride, or the like. The material layer may be formed by, for example, a chemical vapor deposition method.

The composition for a resist underlayer film may be prepared in a solution form and applied by a spin-on coating method. At this time, the coating thickness of the composition for a resist underlayer film is not particularly limited, but it may be applied to a thickness of about 100 to 10,000 angstroms, for example.

The step of exposing the resist layer may be performed using, for example, ArF, KrF or EUV. Further, the heat treatment process can be performed at about 90 to 500 ° C after exposure.

The step of etching the exposed portion of the material layer may be performed by dry etching using an etching gas, and the etching gas may be, for example, CHF ₃ , CF ₄ , Cl ₂ , BCl ₃ and a mixed gas thereof.

The etched material layer may be formed in a plurality of patterns, and the plurality of patterns may be a metal pattern, a semiconductor pattern, an insulation pattern, or the like, and may be applied to various patterns in a semiconductor integrated circuit device, for example.

Hereinafter, embodiments of the present invention will be described in detail with reference to examples. The following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

Cyanuric acid  Synthesis of derivatives

Synthetic example  One

3.0 g of tris- (2,3-epoxypropyl) -isocyanurate (a) was dissolved in 40 g of tetrahydrofuran (THF). 5.0637 g of mercaptobenzothiazole (b) and 0.17 g of benzyltriethylammonium chloride were added to the solution, followed by reaction at 70 ° C for 24 hours. After the reaction, the resultant was dissolved in methylene chloride, precipitated slowly in a solvent of n-hexane, and the resulting precipitate was filtered. Subsequently, the filtered precipitate was dried in a vacuum oven maintained at 50 캜 for about 24 hours to obtain a cyanuric acid derivative represented by the following formula (c).

[Reaction Scheme 1]

Synthetic example  2

3.0 g of tris- (2,3-epoxypropyl) -isocyanurate (a) was dissolved in 40 g of tetrahydrofuran (THF). To this solution, 4.5475 g of mercaptobenzimidazole (d) and 0.17 g of benzyltriethylammonium chloride were added, followed by reaction at 70 ° C for 24 hours. After the reaction, the precipitate was dissolved in methylene chloride, precipitated slowly in a hexane solvent, and the resulting precipitate was filtered. Subsequently, the filtered precipitate was dried in a vacuum oven maintained at 50 캜 for about 24 hours to obtain a cyanuric acid derivative represented by the following formula (e).

[Reaction Scheme 2]

Synthesis of Photosensitive Polymer

Synthetic example  3

To a flask under a nitrogen atmosphere, 40 mmol of? -Butyrolactonyl methacrylate (GBLMA), 40 mmol of hydroxyisopropyl methacrylate, 4-hydroxyphenyl methacrylate ) And methyl ethyl ketone (solvent, about twice the total weight of the monomers) were added and mixed. 10 mmol of dimethyl-2,2'-azobis (2-methylpropionate) (V601, manufactured by Wako Chemicals) as a polymerization initiator was added thereto, followed by addition at a temperature of 80 ° C for about 4 hours by syringe, And further polymerized.

After completion of the polymerization, the obtained polymer was slowly precipitated in an excessive amount of hexane solvent, and the resulting precipitate was filtered, and the precipitate was again dissolved in an appropriate amount of a mixed solvent of n-hexane / isopropanol (IPA) and stirred. Subsequently, the obtained precipitate was dried in a vacuum oven maintained at 50 캜 for about 24 hours to obtain a photosensitive polymer represented by the following formula (2).

(2)

(a=40, b=40, c=20)

(a = 40, b = 40, c = 20)

The yield was 75%. The weight average molecular weight (Mw) of the obtained photosensitive polymer was 7,903 and the dispersion degree (Mw / Mn) was 1.4.

Resist For bottom layer  Preparation of composition

Example  One

0.5 g of the cyanuric acid derivative obtained in Synthesis Example 1, 1.5 g of the photosensitive polymer obtained in Synthesis Example 3, 0.3 g of a glycoluril compound (PD1174, manufactured by TCI) having a structure of the formula A as a crosslinking agent as described below, (PGMEA) / propylene glycol monomethyl ether (PGME) (7/3 v / v) was added to 100 g of pyridinium para-toluenesulfonate (pPTS) Followed by melting and filtration to prepare a composition for a resist underlayer film.

Example  2

A composition for a resist underlayer film was prepared in the same manner as in Example 1, except that the cyanuric acid derivative obtained in Synthesis Example 2 was used instead of the cyanuric acid derivative obtained in Synthesis Example 1.

Comparative Example  One

A composition for a resist underlayer film was prepared in the same manner as in Example 1, except that the cyanuric acid derivative obtained in Synthesis Example 1 was not included.

Resist Bottom layer  formation

On the silicon wafer, the compositions according to Examples 1 and 2 and Comparative Example 1 were applied by a spin-on coating method, and then heat-treated on a hot plate at 205 ° C for 1 minute to form a resist underlayer film having a thickness of about 100 Å.

Evaluation - 1: Film density

The density of the resist underlayer film formed from the composition according to Examples 1 and 2 and Comparative Example 1 was measured. 　 The density of the lower layer film was measured using an X-Ray Diffractometer (Model: X'Pert PRO MPD, manufactured by Panalytical (Netherlands)).

The results are shown in Table 1.

Density (g / cm3) Example 1 1.40 Example 2 1.39 Comparative Example 1 1.26

Referring to Table 1, it can be seen that the film formed using the composition according to Examples 1 and 2 has a higher density than the film formed using the composition according to Comparative Example 1. [ From this, it can be seen that when the composition according to Examples 1 and 2 is used, a resist lower layer film having a more dense structure can be formed, thereby effectively preventing infiltration of contaminants that can be eluted from the substrate.

Evaluation - 2: Degree of elution in solvent and developer

The under-layer resist film formed from the composition according to Examples 1 and 2 and Comparative Example 1 was dissolved in a single solvent of propylene glycol monomethyl ether (PGME), which is a solvent mainly used for a resist, and propylene glycol monomethyl ether acetate (PGMEA) / cyclohexanone cyclohexanone, or Anone) (5/5 v / v) mixed solvent and a 2.38 wt% aqueous solution of tetramethyl ammonium hydroxid (TMAH), which is mainly used as a developer for forming a resist pattern.

The thickness of the initial resist lower layer film and the thickness of the resist lower layer film after immersion were compared to confirm the degree of elution into the solvent and the developing solution.

The results are shown in Table 2.

Solvent or developer Initial thickness (Å) Thickness after immersion (Å) Thickness change (Å) Thickness change ratio (%) Example 1 PGME 107.35 107.46 0.11 0.10 PGMEA / Anone 104.95 105.16 0.21 0.20 TMAH 106.96 106.90 -0.06 -0.06 Example 2 PGME 104.06 103.66 -0.40 -0.38 PGMEA / Anone 104.25 104.22 -0.03 -0.03 TMAH 105.08 105.16 0.08 0.08 Comparative Example 1 PGME 105.81 103.34 -2.47 -2.33 PGMEA / Anone 103.27 101.00 -2.27 -2.20 TMAH 108.83 105.49 -3.34 -3.07

Referring to Table 2, the compositions according to Examples 1 and 2 were hardly eluted in the solvent or the developer used in the resist, whereas the composition according to Comparative Example 1 eluted in the solvent or the developer to significantly decrease the film thickness .

Evaluation - 3: Exposure characteristics

A resist solution was coated on the lower resist film formed from the compositions according to Examples 1 and 2 and Comparative Example 1 by a spin-on coating method, and then heat-treated at 110 ° C for 1 minute on a hot plate to form a resist layer.

The resist layer was exposed using a e-beam exposure machine (manufactured by Elionix, with an acceleration voltage of 100 keV) at a line width of 30 nm and a space between the lines of 30 nm. Subsequently, the resist film was heat-treated at 95 ° C for 60 seconds, developed with a 2.38 wt% aqueous solution of tetramethylammonium hydroxide (TMAH) for 60 seconds, and rinsed with pure water for 15 seconds to form a resist pattern.

The resolution, line-width roughness (LWR) and development residue of the resist pattern were evaluated.

The line-width roughness LWR was observed with a scanning electron microscope (SEM) S-9260 (manufactured by Hitachi) with respect to a pattern formed with a width of 30 nm, and an edge was observed with respect to an edge 2 mu m in the longitudinal direction of the pattern The distance from the baseline was measured. The smaller the value of the line-width roughness (LWR) is, the better.

The development residue is based on the dissolution rate (DR) in a 2.38 wt% aqueous solution of tetramethylammonium hydroxide (TMAH). As the rate increases, the amount of development residue after pattern formation decreases, Observation with a scanning electron microscope (SEM) indicated o in the case of good,? In case of insufficient, and X in case of insufficient.

The results are shown in Table 3.

LWR (nm) Residual residual state Example 1 2.0 ○ Example 2 2.2 ○ Comparative Example 1 3.8 △

Referring to Table 3, it can be seen that the pattern formed using the composition according to Examples 1 and 2 is improved in both LWR, resolution, and development residue compared to the pattern formed using the composition according to Comparative Example 1. [

From this, it can be seen that when the composition according to Examples 1 and 2 is used as a resist lower layer film, the film density, solvent elution property and exposure property are all improved.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.

Claims (11)

A cyanuric acid derivative represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
L ¹ to L ⁶ are each independently a single bond or a substituted or unsubstituted C1 to C30 alkylene group,
R ¹ to R ³ each independently represent the following formula a or b,
(A)

[Formula b]

In the above formula (a) or (b)
R ⁴ to R ¹² are each independently hydrogen or a substituted or unsubstituted C1 to C30 alkyl group,
* Indicates a linking portion with sulfur (S) of formula (1)
The substitution is such that the hydrogen atom is replaced by a halogen atom, a hydroxy group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazino group, a hydrazino group, a carbonyl group, a carbamoyl group, A salt thereof, a salt thereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C30 aryl group, a C7 to C30 arylalkyl group, a C1 to C4 alkoxy group, C20 heteroaryl group, C3 to C20 heteroarylalkyl group, C3 to C30 cycloalkyl group, C3 to C15 cycloalkenyl group, C6 to C15 cycloalkynyl group or C2 to C20 heterocycloalkyl group.
delete delete The method of claim 1,
Wherein the cyanuric acid derivative is a cyanuric acid derivative represented by at least one of the following Chemical Formulas 1a and 1b:
[Formula 1a]

[Chemical Formula 1b]

A cyanuric acid derivative according to any one of claims 1 to 4,
Photosensitive polymer, and
menstruum
Wherein the resist underlayer film is formed of a resist composition.
delete delete delete The method of claim 5,
Wherein the cyanuric acid derivative and the photosensitive polymer are contained in an amount of 0.1 to 5 parts by weight and 0.1 to 30 parts by weight based on 100 parts by weight of the solvent, respectively.
Providing a layer of material over the substrate,
Applying a composition for a resist underlayer film according to claim 5 on the material layer,
Heat-treating the composition for a lower resist film to form a resist lower layer film,
Forming a resist layer on the lower resist film,
Exposing and developing the resist layer to form a resist pattern,
Selectively removing the resist underlayer film using the resist pattern and exposing a part of the material layer, and
Etching the exposed portion of the material layer
≪ / RTI >
11. The method of claim 10,
Wherein the step of applying the composition for a resist underlayer film is performed by a spin-on coating method.