KR20180065652A - Compound, organic layer composition, and method of forming patterns - Google Patents

Abstract

The present invention relates to a compound for an organic film composition represented by chemical formula 1, to an organic film composition comprising the compound, and to a method for forming patterns. In the chemical formula 1, A is a bivalent group containing four substituted or unsubstituted benzene and a double bond in the structure, B is a divalent organic group, and * is a connecting point. One embodiment provides the composition for the organic film composition which has excellent corrosion resistance, and at the same time, ensures gap-fill and planarization properties.

Description

FIELD OF THE INVENTION [0001] The present invention relates to a compound, an organic film composition,

A novel compound, an organic film composition comprising the compound, and a pattern forming method using the organic film composition.

Recently, highly integrated design due to the miniaturization and complexity of electronic devices has accelerated the development of more advanced materials and related processes, so that lithography using existing photoresists also requires new patterning materials and techniques .

In the patterning process, an organic film called a hardmask layer, which is a hard interlayer, can be formed in order to transfer a fine pattern of photoresist to a substrate to a sufficient depth without collapse.

The hard mask layer acts as an interlayer to transfer the fine pattern of the photoresist to the material layer through the selective etching process. Thus, the hardmask layer needs to have corrosion-resisting properties to withstand multiple etching processes.

Meanwhile, it has recently been proposed that the hard mask layer is formed by a spin-on coating method instead of the chemical vapor deposition method.

The spin-on coating method is advantageous in that the deposition process is simple, but the thin film formed by the spin-on coating method generally has a lower etch selectivity than the thin film formed by the chemical or physical vapor deposition method.

One embodiment provides a compound for an organic film composition which has excellent corrosion resistance and at the same time ensures gap-fill and planarization characteristics.

Another embodiment provides an organic film composition that can be applied to a spin-on coating method and can produce a thin film having excellent corrosion resistance and planarization characteristics.

Another embodiment provides a method of forming a pattern using the organic film composition.

According to one embodiment, there is provided a compound comprising a structural unit represented by the following general formula (1).

[Chemical Formula 1]

[Chemical Formula 1]

In Formula 1,

A is a divalent group containing four substituted or unsubstituted benzene and a double bond in its structure,

B is a divalent organic group,

* Is the connection point.

In Formula 1, A may include a substituted or unsubstituted tetraphenylethylene moiety.

B in the formula (1) may be represented by the following formula (2) or (3).

(2)

In Formula 2,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted benzene ring or an aromatic ring in which 2 to 4 substituted or unsubstituted benzene rings are fused,

L is a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof,

* Is the connection point:

(3)

In Formula 3,

X is a substituted or unsubstituted C6 to C30 aromatic ring group,

X 'is hydrogen or a substituted or unsubstituted C6 to C30 aromatic ring group,

L is a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof,

* Is the connection point.

In Formula 2, Ar ¹ and Ar ² are each independently any of substituted or unsubstituted aromatic rings selected from the following Group 1.

[Group 1]

In Formula 1, B may be any of the substituted or unsubstituted divalent groups listed in Group 2 below.

[Group 2]

In Formula 3, X and X 'may each independently be any of substituted or unsubstituted moieties selected from Group 3 below.

[Group 3]

The compound may have a weight average molecular weight of 1,000 to 200,000.

According to another embodiment, there is provided an organic film composition comprising the above-described compound, and a solvent.

According to another embodiment, there is provided a method of manufacturing a semiconductor device, comprising: forming a material layer on a substrate; applying an organic film composition including the above-described compound and a solvent on the material layer; Containing thin film layer on the hard mask layer; forming a photoresist layer on the silicon-containing thin film layer; exposing and developing the photoresist layer to form a photoresist pattern; Selectively removing the silicon-containing thin film layer and the hard mask layer and exposing a portion of the material layer, and etching the exposed portion of the material layer.

The step of applying the organic film composition may be performed by a spin-on coating method.

And forming a bottom anti-reflective layer (BARC) before the step of forming the photoresist layer.

By using a novel compound as an organic film material, it is possible to provide an organic film having excellent etching selectivity while ensuring gap-fill property and flatness.

FIG. 1 is a flow chart for explaining a pattern forming method according to an embodiment,
Fig. 2 is a reference diagram for explaining a method of evaluating the planarization characteristic.

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 the 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 thio group, an ester 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, A C 1 to C 30 arylalkyl group, a C 7 to C 30 arylalkyl group, a C 1 to C 30 alkoxy group, a C 1 to C 20 heteroalkyl group, a C 3 to C 20 heteroarylalkyl group, a C 3 to C 30 cycloalkyl group, a C 3 to C 15 cycloalkenyl group, C6 to C15 cycloalkynyl groups, C3 to C30 heterocycloalkyl groups, and combinations thereof.

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

Also, unless otherwise defined herein, '*' refers to the point of attachment of a compound or moiety.

The compounds according to one embodiment are described below.

The compound according to one embodiment includes a structural unit represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

A is a divalent group containing four substituted or unsubstituted benzene and a double bond in its structure,

B is a divalent organic group,

* Is the connection point.

For example, A may include a substituted or unsubstituted tetraphenylethylene moiety, which may be represented by the following formula (X).

 (X)

In the above formula (X)

Each of R ¹ to R ⁴ independently represents a hydroxyl group, a halogen group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, Substituted C1 to C30 heteroalkyl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, or combinations thereof,

a to d each independently represent an integer of 0 to 3;

In Formula X, at least one of a to d may be one or more, and in this case, R ¹ to R ⁴ may be a hydroxy group.

The solubility of the compound for organic film composition can be further improved by controlling the kinds and number of the functional groups represented by R ¹ to R ⁴ to form a gap-fill capable of filling the gaps between the patterns when formed by the spin- Characteristics and planarization characteristics can be ensured.

The compound contains a tetraphenylethene moiety in its structural unit and can be used, for example, as an organic film (e.g., a hard mask layer) material. The compound is basically excellent in corrosion resistance by containing four benzene rings in its structure, and the flexibility of the molecule can be secured by having a structure in which the four benzene rings are connected to ethylene.

In the above formula (1), B is a divalent organic group containing at least one benzene ring and a tertiary carbon or a quaternary carbon in its structure.

In the present specification, 'tertiary carbon' is a carbon in which all three of four hydrogen atoms bonded to carbon are substituted with other groups than hydrogen, and 'quaternary carbon' means that four hydrogen atoms bonded to carbon Is defined as a carbon in which all of the carbon atoms are replaced with groups other than hydrogen.

The compound has an improved solubility by containing tertiary carbon or quaternary carbon in the organic group represented by B, which is advantageous for application to the spin-on coating method.

For example, B in the formula (1) may be represented by the following formula (2) or (3), but is not limited thereto.

(2)

In Formula 2,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted benzene ring or an aromatic ring in which 2 to 4 substituted or unsubstituted benzene rings are fused,

L is a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof,

* Is the connection point:

(3)

In Formula 3,

X is a substituted or unsubstituted C6 to C30 aromatic ring group,

X 'is hydrogen or a substituted or unsubstituted C6 to C30 aromatic ring group,

L is a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof,

* Is the connection point.

For example, in Formula 2, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted aromatic ring selected from the following Group 1, but are not limited thereto.

[Group 1]

The position in which the aromatic rings listed in the group 1 are bonded to the formula (2) is not limited. The aromatic rings listed in the group 1 may be in an unsubstituted form, and examples thereof include a hydroxyl group, a halogen group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted A C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

For example, in Formula 1, B may be any of substituted or unsubstituted bivalent groups listed in Group 2, but is not limited thereto.

[Group 2]

The bivalent groups listed in the group 2 may be unsubstituted or substituted with at least one selected from the group consisting of a hydroxyl group, a halogen group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

For example, in Formula 3, X and X 'each independently represent a substituted or unsubstituted aromatic ring selected from the following Group 3, but are not limited thereto.

[Group 3]

The positions where the aromatic ring groups listed in the group 3 are bonded to the formula 3 are not limited. The aromatic rings listed in the group 1 may be in an unsubstituted form, and examples thereof include a hydroxyl group, a halogen group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted A C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

The number of the structural unit represented by the formula (1) contained in the compound is not limited. For example, the compound may include a heterogeneous structural unit represented by the formula (1).

The compound may have a weight average molecular weight of about 1,000 to 200,000. More specifically, the compound may have a weight average molecular weight of about 1,500 to 20,000. By having a weight average molecular weight in the above range, it is possible to optimize by controlling the carbon content of the organic film composition (for example, hard mask composition) containing the compound and the solubility in solvents.

When the above compound is used as an organic film material, it is possible to form a uniform thin film without forming pin-holes and voids or deteriorate thickness scattering in the baking process, or when a step is present in the lower substrate (or film) It is possible to provide excellent gap-fill and planarization characteristics. In addition, it can be easily removed by deionized water (DIW) after the etching process, and a flat film quality can be realized.

According to another embodiment, there is provided an organic film composition comprising the above-described compound, and a solvent.

The solvent is not particularly limited as long as it has sufficient solubility or dispersibility in the compound. Examples of the solvent include propylene glycol, propylene glycol diacetate, methoxypropanediol, diethylene glycol, diethylene glycol butyl ether, tri (ethylene glycol) But are not limited to, methyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, ethyl lactate, gamma-butyrolactone, N, N-dimethylformamide, , Methyl pyrrolidinone, acetylacetone, and ethyl 3-ethoxypropionate.

The compound may be included in an amount of about 0.1 to 50% by weight, about 0.1 to 30% by weight, or about 0.1 to 15% by weight based on the total amount of the organic film composition. By including the compound in the above range, the thickness, surface roughness and planarization degree of the organic film can be controlled.

The organic film composition may further include additives such as a surfactant, a crosslinking agent, a thermal acid generator, and a plasticizer.

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

Examples of the cross-linking agent include melamine-based, substitution-based, or polymer-based ones. Preferably, the crosslinking agent having at least two crosslinking substituents is, for example, a methoxymethylated glycerol, a butoxymethylated glyceryl, a methoxymethylated melamine, a butoxymethylated melamine, a methoxymethylated benzoguanamine, a butoxy Methylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, or butoxymethylated thiourea can be used.

As the crosslinking agent, a crosslinking agent having high heat resistance can be used. As the crosslinking agent having a high heat resistance, a compound containing a crosslinking forming substituent group having an aromatic ring (for example, a benzene ring or a naphthalene ring) in the molecule can be used.

The acid generator may be an acidic compound such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid or naphthalenecarboxylic acid and / , 4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and other organic sulfonic acid alkyl esters, but are not limited thereto.

The additive may be included in an amount of about 0.001 to 40 parts by weight based on 100 parts by weight of the organic film composition. By including it in the above range, the solubility can be improved without changing the optical properties of the organic film composition.

According to another embodiment, there is provided an organic film produced using the organic film composition described above. The organic layer may be in the form of a hardened layer, for example, a hard mask layer, a planarization layer, a sacrificial layer, a filler, etc., and an organic thin film used for electronic devices, .

Hereinafter, a method of forming a pattern using the above-described organic film composition will be described with reference to FIG.

1 is a flowchart illustrating a pattern forming method according to an embodiment.

The pattern forming method according to one embodiment includes forming a material layer on a substrate (S1), applying (S2) an organic film composition including the above-described compound and a solvent on the material layer, Forming a hard mask layer (S3) on the hard mask layer, forming a silicon-containing thin film layer on the hard mask layer (S4), forming a photoresist layer on the silicon-containing thin film layer (S5) (S6) selectively removing the silicon-containing thin film layer and the hard mask layer using the photoresist pattern and exposing a part of the material layer using the photoresist pattern, And etching the exposed portion of the material layer (S8).

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 organic film composition is as described above, and may be prepared in a solution form and applied by a spin-on coating method. At this time, the coating thickness of the organic film composition is not particularly limited, but may be applied to a thickness of about 50 to 10,000 ANGSTROM.

The heat treatment of the organic film composition may be performed at about 100 to 500 DEG C for about 10 seconds to 1 hour.

The silicon-containing thin film layer may be formed of a material such as SiCN, SiOC, SiON, SiOCN, SiC, SiO and / or SiN.

Further, a bottom anti-reflective coating (BARC) may be further formed on the silicon-containing thin film layer before the step of forming the photoresist layer.

The step of exposing the photoresist layer may be performed using, for example, ArF, KrF or EUV. Further, after the exposure, the heat treatment process may be performed at about 100 to 500 ° C.

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.

Synthetic example

Synthetic example  One

To a 500 mL 2-neck round-bottomed flask equipped with a condenser was added 33.2 g (0.10 mol) of tetraphenylethhene, 18.0 g (0.10 mol) of 9-fluorenone and 19.0 g of p-toluenesulfonic acid monohydrate 0.10 mol) and 62 g of 1,4-dioxane, and the mixture was stirred at 110 DEG C for 24 hours to 48 hours to effect polymerization. The reaction was completed when the weight average molecular weight was 1,000 to 1,500. After completion of the polymerization reaction, the reaction product was slowly cooled to room temperature. The reaction product was diluted with 300 g of ethyl acetate, and washed with 300 g of distilled water 10 times. The organic layer was concentrated under reduced pressure, diluted again with 200 g of THF, and added dropwise to 1 kg of nucleic acid to obtain a precipitate. The precipitate was filtrated and dissolved again in 200 g of THF, and the solution was slowly added dropwise to 1 kg of nucleic acid to obtain a precipitate. After filtration and drying, a compound (MW: 1,200) containing a structural unit represented by Compound A was obtained.

(A)

Synthetic example  2

Except that 4,4 ', 4 ", 4' '- (Ethene-1,1,2,2-tetrayl) tetraphenol was used instead of tetraphenylethene in Synthesis Example 1 and pyrene aldehyde was used instead of 9- A compound (MW: 1,400) containing a structural unit represented by the following formula (B) was obtained.

[Chemical Formula B]

Synthetic example  3

Except that 4,4 ', 4' ', 4' '' - (Ethene-1,1,2,2-tetrayl) tetraphenol was used instead of tetraphenylethene in Synthesis Example 1 and 9-penanthrenecarbaldehyde was used in place of 9- Using the same method, a compound (MW: 1,400) containing a structural unit represented by the following formula (C) was obtained.

≪ RTI ID = 0.0 &

Comparative Synthetic Example  One

A compound (MW: 1,300) containing a structural unit represented by the following formula (D) was obtained by using the same method as in Synthesis Example 1, except that pyrene was used instead of tetraphenylethene.

[Chemical Formula D]

Comparative Synthetic Example  2

(MW: 1,500) containing the structural unit represented by the following formula (E) was obtained in the same manner as in Synthesis Example 1, except that indole was used instead of tetraphenylethene.

(E)

Hard mask  Preparation of composition

Example  One

3.0 g of the compound obtained in Synthesis Example 1 was dissolved in 17 g of propylene glycol monomethyl ether acetate (PGMEA), followed by filtration through a 0.1 탆 Teflon filter to prepare a hard mask composition.

Example  2

A hard mask composition was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 2 was used instead of the compound obtained in Synthesis Example 1.

Example  3

A hard mask composition was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 3 was used instead of the compound obtained in Synthesis Example 1.

Comparative Example  One

A hard mask composition was prepared in the same manner as in Example 1, except that the compound obtained in Comparative Synthesis Example 1 was used instead of the compound obtained in Synthesis Example 1.

Comparative Example  2

A hard mask composition was prepared in the same manner as in Example 1, except that the compound obtained in Comparative Synthesis Example 2 was used instead of the compound obtained in Synthesis Example 1.

Evaluation 1: Gap-fill characteristic and planarization characteristic

The hard mask composition according to Examples 1 to 3 and Comparative Examples 1 and 2 was spin-coated on a silicon wafer by adjusting the mass ratio of solvent to solute to 7 to 93, and then subjected to a baking process, Respectively. Under the above conditions, the thickness of the mask on the bare wafer became about 1100 Å.

The gap-fill and planarization characteristics were determined by observing the cross-section of the pattern using a scanning electron microscope (SEM) to determine whether or not a void was generated. The planarization characteristic was evaluated as a step difference (h ₁ -h ₂ ) Were measured. Referring to FIG. 2, h ₁ denotes a value obtained by averaging thicknesses of thin films measured at arbitrary three points where no pattern is formed in the substrate, h ₂ denotes a value measured at any three points where a pattern is formed on the substrate Means the thickness of one thin film. Referring to FIG. 2, the planarization characteristic is superior as the difference between h ₁ and h ₂ is small.

Presence or absence of void Step (nm) Example 1 none 79 Example 2 none 95 Example 3 none 83 Comparative Example 1 has exist 229 Comparative Example 2 none 224

Referring to Table 1, it can be seen that the thin film formed from the hard mask composition according to Examples 1 to 3 has a much smaller step value as compared with the thin film formed from the hard mask composition according to Comparative Examples 1 to 2, Can be confirmed. In addition, no void was observed in the thin film formed from the hard mask composition according to Examples 1 to 3, and it was confirmed that the gap-fill characteristic was excellent.

Evaluation 2: Awareness of corrosion

The hard mask composition according to Examples 1 to 3 and Comparative Examples 1 and 2 was spin-coated on a silicon wafer and then heat-treated at 400 ° C for 2 minutes on a hot plate to form a thin film having a thickness of 4,000 Å, Respectively. Subsequently, the thin film was dry-etched for 100 seconds and 60 seconds using CHF ₃ / CF ₄ mixed gas and N ₂ / O ₂ mixed gas, respectively, and then the thickness of the thin film was measured again. The bulk etch rate (BER) was calculated from the thickness and etch time of the thin film before and after dry etching according to the following equation.

[Equation 1]

The bulk etch rate (BER) = (initial thin film thickness - thin film thickness after etching) / etching time (Å / s)

The results are shown in Table 2.

CF _x N ₂ / O ₂ Example 1 24.53 22.31 Example 2 24.42 21.17 Example 3 24.17 21.63 Comparative Example 1 26.02 25.58 Comparative Example 2 28.71 26.42

Referring to Table 2, the thin films formed from the hard mask compositions according to Examples 1 to 3 had sufficient erosion resistance to the etching gas as compared with the thin films formed from the hard mask composition according to Comparative Examples 1 to 2, thereby improving bulk etch characteristics can confirm.

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 (17)

1. A compound for an organic film composition comprising a structural unit represented by the following formula
[Chemical Formula 1]

In Formula 1,
A is a divalent group containing four substituted or unsubstituted benzene and a double bond in its structure,
B is a divalent organic group,
* Is the connection point. The method of claim 1,
Wherein A in Formula 1 is a substituted or unsubstituted tetraphenylethylene moiety. The method of claim 1,
Wherein B in the above formula (1) is represented by the following formula (2) or (3):
(2)

In Formula 2,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted benzene ring or an aromatic ring in which 2 to 4 substituted or unsubstituted benzene rings are fused,
L is a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof,
* Is the connection point:
(3)

In Formula 3,
X is a substituted or unsubstituted C6 to C30 aromatic ring group,
X 'is hydrogen or a substituted or unsubstituted C6 to C30 aromatic ring group,
L is a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof,
* Is the connection point. 4. The method of claim 3,
Wherein Ar ¹ and Ar ² are each independently any one selected from substituted or unsubstituted aromatic rings selected from the following Group 1:
[Group 1]

4. The method of claim 3,
Wherein B in Formula 1 is any one of substituted or unsubstituted divalent groups listed in Group 2:
[Group 2]

4. The method of claim 3,
In Formula 3, X and X 'are each independently any one selected from the group consisting of a substituted or unsubstituted moiety selected from the following Group 3:
[Group 3]

The method of claim 1,
And a weight average molecular weight of 1,000 to 200,000. A compound for an organic film composition comprising a structural unit represented by the following formula (1), and
menstruum
: ≪ / RTI >
[Chemical Formula 1]

In Formula 1,
A is a divalent group containing four substituted or unsubstituted benzene and a double bond in its structure,
B is a divalent organic group,
* Is the connection point. 9. The method of claim 8,
Wherein A in Formula 1 is a substituted or unsubstituted tetraphenylethylene moiety. 9. The method of claim 8,
Wherein B in the formula (1) is represented by the following formula (2) or (3):
(2)

In Formula 2,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted benzene ring or an aromatic ring in which 2 to 4 substituted or unsubstituted benzene rings are fused,
L is a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof,
* Is the connection point:
(3)

In Formula 3,
X is a substituted or unsubstituted C6 to C30 aromatic ring group,
X 'is hydrogen or a substituted or unsubstituted C6 to C30 aromatic ring group,
L is a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof,
* Is the connection point. 11. The method of claim 10,
Wherein Ar ¹ and Ar ² are each independently any one selected from substituted or unsubstituted aromatic rings selected from the following Group 1:
[Group 1]

11. The method of claim 10,
Wherein B in Formula 1 is any one of substituted or unsubstituted divalent groups listed in Group 2 below:
[Group 2]

11. The method of claim 10,
Wherein X and X 'are each independently any one selected from substituted or unsubstituted moieties selected from the following Group 3:
[Group 3]

9. The method of claim 8,
Wherein the organic film composition compound has a weight average molecular weight of 1,000 to 200,000. Providing a layer of material over the substrate,
Applying the organic film composition according to any one of claims 8 to 14 on the material layer,
Heat treating the organic film composition to form a hard mask layer,
Forming a silicon-containing thin film layer on the hard mask layer,
Forming a photoresist layer on the silicon-containing thin film layer,
Exposing and developing the photoresist layer to form a photoresist pattern
Selectively removing the silicon-containing thin film layer and the hard mask layer using the photoresist pattern and exposing a portion of the material layer, and
Etching the exposed portion of the material layer
≪ / RTI > 16. The method of claim 15,
Wherein the step of applying the organic film composition is performed by a spin-on coating method. 16. The method of claim 15,
Further comprising forming a bottom anti-reflective layer (BARC) before the step of forming the photoresist layer.

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