KR20150002931A - Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition - Google Patents

Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition Download PDF

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KR20150002931A
KR20150002931A KR20130073949A KR20130073949A KR20150002931A KR 20150002931 A KR20150002931 A KR 20150002931A KR 20130073949 A KR20130073949 A KR 20130073949A KR 20130073949 A KR20130073949 A KR 20130073949A KR 20150002931 A KR20150002931 A KR 20150002931A
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group
substituted
unsubstituted
hard mask
monomer
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KR20130073949A
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Korean (ko)
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송현지
김윤준
김고은
김영민
김혜정
문준영
박요철
박유신
박유정
신승욱
윤용운
이충헌
최유정
홍승희
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제일모직주식회사
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Priority to KR20130073949A priority Critical patent/KR20150002931A/en
Priority to TW103103336A priority patent/TWI541611B/en
Priority to US14/258,489 priority patent/US10345706B2/en
Priority to CN201410163675.8A priority patent/CN104250228B/en
Publication of KR20150002931A publication Critical patent/KR20150002931A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/265—Selective reaction with inorganic or organometallic reagents after image-wise exposure, e.g. silylation
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
    • H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/46—Manufacturing multilayer circuits

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  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Power Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Computer Hardware Design (AREA)
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  • Structural Engineering (AREA)
  • Materials For Photolithography (AREA)

Abstract

A hard mask composition comprising the monomer, and a pattern forming method using the same.
[Chemical Formula 1]

Figure pat00043

A, A ', L, X, X', X "and k, m and n are as defined in the specification.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hard mask composition comprising a monomer for a hard mask composition, a hard mask composition comprising the monomer, and a pattern forming method using the hard mask composition. BACKGROUND OF THE INVENTION 1. Field of the Invention [0001]

A hard mask composition comprising the monomer, and a pattern forming method using the hard mask composition.

BACKGROUND ART [0002] In recent years, the semiconductor industry has developed into an ultrafine technology having a pattern of a few to a few nanometers in a pattern of a size of several hundred nanometers. Effective lithographic techniques are essential to realize this ultrafine technology.

A typical lithographic technique involves forming a material layer on a semiconductor substrate, coating a photoresist layer thereon, exposing and developing the photoresist layer to form a photoresist pattern, and etching the material layer using the photoresist pattern as a mask do.

In recent years, as the size of a pattern to be formed decreases, it is difficult to form a fine pattern having a good profile only by the typical lithographic technique described above. Accordingly, a layer called a hardmask layer may be formed between the material layer to be etched and the photoresist layer to form a fine pattern.

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. Therefore, the hard mask layer is required to have properties such as chemical resistance, heat resistance and etching resistance so as to withstand the multiple etching process.

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 can use a hard mask composition having solubility in solvents.

However, there is a need for a hard mask composition capable of satisfying both of the above-mentioned properties and solubility required for a hard mask layer in a trade-off relationship with each other.

One embodiment provides a monomer for a hard mask composition that is capable of satisfying chemical resistance, heat resistance, and etching resistance while ensuring solubility in a solvent.

Another embodiment provides a hardmask composition comprising the monomer.

Another embodiment provides a method of pattern formation using the hardmask composition.

According to one embodiment, there is provided a monomer for a hard mask composition represented by the following formula:

[Chemical Formula 1]

Figure pat00001

In Formula 1,

A and A 'are the same or different substituted or unsubstituted aromatic groups,

X, X 'and X "each independently represents a substituent selected from the group consisting of a hydroxyl group, a halogen atom, a halogen-containing group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1- Or a substituted or unsubstituted C6 to C30 aryl group, 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 C1 to C20 alkylamine 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 C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkoxy A substituted or unsubstituted C1 to C20 aldehyde group, a substituted or unsubstituted C1 to C4 alkyl ether, a substituted or unsubstituted C7 to C20 arylalkylene ether, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof ego,

L is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group or a combination thereof,

n is an integer of 1 to 5,

When p is the maximum number of substituents that A can have, k is an integer satisfying 0? k? p-n-1,

and q is an integer satisfying 0? m? q-2 when A 'is the maximum number of substituents that A' can have.

Each of A and A 'may independently be a substituted or unsubstituted aromatic group selected from the groups listed in Group 1 below.

[Group 1]

Figure pat00002

In the group 1,

Z 1 represents a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl (O), sulfur (S), or a combination thereof, wherein R is a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, a is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group,

Z 3 to Z 18 each independently represent C = O, NR a , oxygen (O), sulfur (S), CR b R c Or a combination thereof, wherein each of R a to R c is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group , A halogen atom, a halogen-containing group, or a combination thereof.

At least one of A and A 'may include a substituted or unsubstituted polycyclic aromatic group.

The monomer may be represented by the following general formula (2) or (3).

(2)

Figure pat00003

(3)

Figure pat00004

In the above Formulas 2 and 3,

A 0 to A 3 each independently represent a substituted or unsubstituted benzene group, a naphthalene group, a pyrene group, a benzopyrylene group, a perylene group, a benzoperylene group, a coronene group,

X 1 to X 6 each independently represent a hydroxyl group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a halogen atom, a halogen-containing group, a substituted or unsubstituted C1 to C30 alkoxy group, Substituted C1 to C20 alkylborane, substituted or unsubstituted C6 to C30 arylborane, or combinations thereof.

The monomer may be represented by any one of the following formulas (4) to (8).

 [Chemical Formula 4]

Figure pat00005

[Chemical Formula 5]

Figure pat00006

[Chemical Formula 6]

Figure pat00007

(7)

Figure pat00008

[Chemical Formula 8]

Figure pat00009

The monomer may have a molecular weight of from 200 to 5,000.

According to another embodiment, there is provided a hard mask composition comprising a monomer represented by Formula 1 and a solvent.

The monomer may be included in an amount of 0.1% to 50% by weight based on the total amount of the hard mask composition.

Comprising the steps of: providing a layer of material over a substrate; applying the hardmask composition described above on the layer of material; heat treating the hardmask composition to form a hardmask layer; forming a thin layer of silicon- Forming a photoresist layer on the silicon-containing thin film layer; exposing and developing the photoresist layer to form a photoresist pattern; selectively etching 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.

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

The step of forming the hard mask layer may include a heat treatment at 100 ° C to 500 ° C.

And forming a bottom anti-reflection layer (BARC) on the silicon-containing thin film layer.

The silicon-containing thin film layer may be one containing silicon oxynitride (SiON).

The present invention provides a hard mask composition capable of satisfying solubility in a solvent and securing chemical resistance, heat resistance and etching resistance.

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C1 to C20 alkylboranyl group, a substituted or unsubstituted C1 to C20 alkylsulfonyl group, A substituted or unsubstituted C6 to C30 arylborane group, 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, A C1 to C20 heteroalkyl group, a C3 to C20 heteroarylalkyl group, a C3 to C30 cycloalkyl group, a C3 to C15 cycloalkenyl group, a C6 to C15 cycloalkynyl group, a C2 to C30 heterocycloalkyl group, It means substituted with a substituent selected.

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

The monomers for the hard mask composition according to one embodiment will be described below.

The monomer for a hard mask composition according to one embodiment may be represented by the following formula (1).

[Chemical Formula 1]

Figure pat00010

In Formula 1,

A and A 'are the same or different substituted or unsubstituted aromatic groups,

X, X 'and X "each independently represents a hydroxyl group, a halogen atom, a halogen-containing group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1- A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C7 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy 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 C1 to C4 alkyl A substituted or unsubstituted C7 to C20 arylalkylene ether, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C1 to C20 alkylboranyl group, a substituted or unsubstituted C6 to C30 arylborane group, A combination thereof,

L is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof.

The monomer has a structure in which an aromatic group is contained in a core and a substituent, respectively. The monomers may have rigid properties by having a plurality of aromatic groups.

The monomer includes a predetermined functional group (X, X 'and X ") in the core and the substituent, respectively. By including such functional groups, the solubility is improved and can be effectively formed by the spin-on coating method. In addition, the gap-fill characteristic and the planarization characteristic that can fill the gaps between the patterns when formed by the spin-on coating method on the lower film having a predetermined pattern are also excellent.

Also, it is possible to perform amplification crosslinking based on the condensation reaction of the plurality of functional groups, thereby exhibiting excellent crosslinking properties. Accordingly, even when the monomer is heat-treated at a relatively low temperature, the monomer can be crosslinked in a high molecular weight polymer in a short time, thereby exhibiting properties required in a hard mask layer such as excellent mechanical properties, heat resistance characteristics and corrosion resistance.

In the above formula (1), n means the number of substituents containing an aromatic group, and may be selected within the range of 1 to 5, depending on the intended physical properties.

In the formula (1), k means the number of the functional group X. When p is the maximum number of substituents A can have, k satisfies 0? k? p-n-1. That is, the core represented by A in Formula 1 contains at least one unsubstituted hydrogen.

In the formula (1), m represents the number of the functional group X ". When q is the maximum number of substituents that A 'can have, m satisfies 0? m? q-2. That is, the aromatic group in the substituent represented by A 'in the above formula (1) includes at least one unsubstituted hydrogen.

Each of A and A 'may independently be a substituted or unsubstituted aromatic group selected from the groups listed in Group 1 below.

[Group 1]

Figure pat00011

In the group 1,

Z 1 represents a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl (O), sulfur (S), or a combination thereof, wherein R is a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, a is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group, a halogen atom,

Z 3 to Z 18 each independently represent C = O, NR a , oxygen (O), sulfur (S), CR b R c Or a combination thereof, wherein each of R a to R c is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group , A halogen atom, a halogen-containing group, or a combination thereof.

In the group 1, the linking position of each ring is not particularly limited, and each ring may be substituted or unsubstituted. When the ring shown in the group 1 is a substituted ring, it may be substituted with, for example, a C1 to C20 alkyl group, a halogen atom, a hydroxy group and the like, but the substituent is not limited.

At least one of A and A 'may be, for example, a substituted or unsubstituted polycyclic aromatic group.

The monomer may be represented, for example, by the following formula (2) or (3).

(2)

Figure pat00012

(3)

Figure pat00013

In the above Formulas 2 and 3,

A 0 to A 3 each independently represent a substituted or unsubstituted benzene group, a naphthalene group, a pyrene group, a benzopyrylene group, a perylene group, a benzoperylene group, a coronene group,

X 1 to X 6 each independently represent a hydroxyl group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a halogen atom, a halogen-containing group, a substituted or unsubstituted C1 to C30 alkoxy group, Substituted C1 to C20 alkylborane, substituted or unsubstituted C6 to C30 arylborane, or combinations thereof.

The monomer may be represented by any one of the following formulas (4) to (8).

[Chemical Formula 4]

Figure pat00014

[Chemical Formula 5]

Figure pat00015

[Chemical Formula 6]

Figure pat00016

(7)

Figure pat00017

[Chemical Formula 8]

Figure pat00018

In the above formula (4), OMe represents a methoxy group.

The monomer may have a molecular weight of from 200 to 5,000. By having a molecular weight in the above range, the monomer having a high carbon content has a good solubility in a solvent, and a good thin film by spin-on coating can be obtained.

The hard mask composition according to one embodiment will be described below.

The hard mask composition according to one embodiment comprises the above-mentioned monomers and a solvent.

The above-mentioned monomers are as described above, and one kind of monomers may be contained singly or two or more kinds of monomers may be mixed and contained.

The solvent is not particularly limited as long as it has sufficient solubility or dispersibility to the monomer. Examples of the solvent include propylene glycol, propylene glycol diacetate, methoxypropanediol, diethylene glycol, diethylene glycol butyl ether, tri (ethylene glycol) At least one selected from methyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, ethyl lactate, gamma-butyrolactone, methylpyrrolidone and acetylacetone.

The monomer may be included in an amount of about 0.1 to 50% by weight based on the total content of the hard mask composition. By incorporating the monomer in the above range, it can be coated with a thin film having a desired thickness.

The hard mask composition may further comprise a surfactant.

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 surfactant may be included in an amount of about 0.001 to 3 parts by weight based on 100 parts by weight of the hard mask composition. By including it in the above range, the solubility can be improved without changing the optical properties of the hard mask composition.

Hereinafter, a method of forming a pattern using the hard mask composition described above will be described.

A patterning method according to one embodiment includes the steps of providing a layer of material on a substrate, applying a hard mask composition comprising the above-mentioned monomers and a solvent on the material layer, heat treating the hard mask composition to form a hard mask 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 using a mask to expose 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 hard mask composition may be prepared in the form of a solution and applied by a spin-on coating method. At this time, the coating thickness of the hard mask composition is not particularly limited, but may be applied to a thickness of, for example, about 100 Å to 10,000 Å.

The heat treatment of the hard mask composition may be performed at a temperature of, for example, about 100 캜 to 500 캜 for about 10 seconds to about 10 minutes. In the heat treatment step, the monomer may cause self-crosslinking and / or cross-linking reaction.

The silicon-containing thin film layer may be made of, for example, silicon nitride, silicon oxide or silicon oxynitride (SiON).

The method may further include forming a bottom anti-reflective coating (BARC) on the silicon-containing thin film layer. For example, a thin film layer containing silicon oxynitride may be formed on the hard mask layer, then a bottom antireflection layer may be formed thereon, and then a photoresist layer may be formed on the bottom antireflection layer.

The step of exposing the photoresist layer may be performed using, for example, ArF, KrF or EUV. Further, a heat treatment process may be performed at about 100 ° C 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 include, for example, CHF 3 , CF 4 , Cl 2 , BCl 3 and a mixed gas thereof. It is not.

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.

Monomeric  synthesis

Synthetic example  One

27.6 g (0.1 mol) of benzoperylene and 48.5 g (0.22 mol) of methoxy naphthoyl chloride were added to 500 g of chloroform / dichloromethane mixed solution to prepare a solution. The solution was stirred using a stirring bar and reacted by adding 61.2 g (0.35 mol) of aluminum chloride little by little.

After completion of the reaction, water was used to remove reaction by-products and unreacted aluminum chloride. The reaction product obtained with the powder was heated (reflux) at 190 ° C for 3 hours with 40 ml of formamide and 5 ml of 85% formic acid. Subsequently, the reaction product was cooled to a temperature of 100 ° C or lower and then added to 250 ml of normal temperature water. The resulting precipitate was filtered and washed with a water / methanol mixture to remove the side reaction product to obtain a compound represented by the following formula 4a .

[Chemical Formula 4a]

Figure pat00019

Synthetic example  2

50.0 g (0.166 mol) of coronene and 83 g (0.499 mol) of 4-iodobenzoyl chloride were added to 700 g of a chloroform / dichloromethane mixed solution to prepare a solution. The solution was stirred using a stirring bar, and 66.6 g (0.499 mol) of aluminum chloride was gradually added thereto, followed by heating to 60 DEG C and stirring for 8 hours.

After completion of the reaction, methanol was added to precipitate the precipitate, which was then filtered and washed with a water / methanol mixture to remove reaction by-products and unreacted aluminum chloride. Pd (II) -anthra catalyst (1.0 mol% Pd) and triethylamine (0.11 mol) were added to 300 ml of a solution of 80.2 g (0.081 mol), K 4 Fe (CN) 6 N, N-Dimethylformamide and then stirred at 100 < 0 > C for 24 hours. After completion of the reaction, the solution was slowly cooled to room temperature, filtered to remove the PS-Pd (II) -anthracene catalyst, and the filtrate was purified by flash column chromatography using silica gel. The obtained powder was dissolved in 300 mL of tetrahydrofuran, and 38 g (1.0 mol) of lithium aluminum hydride (LiAlH 4 ) was added little by little. When the reaction was completed, the reaction side product was removed using a water / methanol mixture to obtain a compound represented by the following formula (5a).

[Chemical Formula 5a]

Figure pat00020

Synthetic example  3

28.2 g (0.1 mol) of methoxybenzopyrene and 23.5 g (0.11 mol) of methoxynaphthoyl chloride were placed in a 500 g of chloroform / dichloromethane mixed solution to prepare a solution. The solution was stirred using a stirring bar, and 36.7 g (0.15 mol) of aluminum chloride was added little by little and reacted at room temperature.

After 1 hour, 21 g (0.11 mol) of naphthoyl chloride was added, and 36.7 g (0.15 mol) of aluminum chloride was further added thereto. After completion of the reaction, water was used to remove reaction by-products and unreacted aluminum chloride. 108.0 g (0.534 mol) of 1-dodecanethiol, 35.9 g (0.640 mol) of potassium hydroxide (KOH) and 300 g of N, N-dimethylformamide were added to the reaction product obtained by the powder Then, the mixture was stirred at 120 ° C for 8 hours. The mixture was then cooled and neutralized to pH 7 using 10% hydrogen chloride solution. Thereafter, the mixture was extracted with ethyl acetate and the powder obtained by rotary evaporation was dissolved in 200 mL of tetrahydrofuran. 18.98 g (0.5 mol) of lithium aluminum hydride was added little by little . After completion of the reaction, the reaction side product was removed using a water / methanol mixture to obtain a compound represented by the following formula (6a).

[Chemical Formula 6a]

Figure pat00021

Synthetic example  4

26.5 g (0.105 mol) of perylene and 10.15 g (0.05 mol) of isophthaloyl chloride were added to 500 g of chloroform / dichloromethane mixed solution to prepare a solution. The solution was stirred using a stirring bar and reacted with a small amount of 29.33 g (0.22 mol) of aluminum chloride. At this time, the reaction was carried out for 2 hours in ice bath to control heat generation.

After the completion of the reaction, water was used to remove reaction by-products and unreacted aluminum chloride, and the reaction product obtained by the powder was filtered and dried. After the dried powder and 270 g of dimethylformamide were added to the flask, 37.83 g (1 mol) of sodium borohydride (NaBH 4 ) was added little by little. When the addition was completed, the mixture was stirred at 50 ° C for 18 hours. After the reaction was completed, the reaction mixture was neutralized to pH 6 with a 7% hydrogen chloride solution, extracted with ethyl acetate, and dried by rotary evaporation. The powder obtained from the drying process was dissolved in 400 ml of dichloromethane and kept at 0 占 폚 in ice bath. 1,8-Diazabicycloundec-7-ene (0.10 mol) was slowly added thereto, and p-Toluenesulfonyl Chloride (0.08 mol) was added thereto in dichloromethane 200 ml. The solution was slowly added, and the ice bath was removed. The temperature was gradually raised to room temperature. After the reaction was allowed to proceed at room temperature for 30 minutes, the reaction product was washed several times with 5% hydrochloric acid and 10% aqueous sodium hydrogencarbonate solution several times to remove reaction by-products, and a monomer represented by the following formula (7a) was obtained from the remaining organic layer.

[Formula 7a]

Figure pat00022

Synthetic example  5

The flask was charged with 50.0 g (0.166 mol) of coronene and 93 g (0.499 mol) of 4-methylthio-benzoyl Chloride with 700 g of a mixture of chloroform / dichloromethane To prepare a solution. The solution was stirred using a stirring bar, and 66.6 g (0.499 mol) of aluminum chloride was gradually added thereto, followed by heating to 60 DEG C and stirring for 8 hours.

After completion of the reaction, methanol was added to precipitate the precipitate, which was then filtered and washed with a water / methanol mixture to remove reaction by-products and unreacted aluminum chloride. 183.6 g (0.908 mol) of 1-dodecanethiol, 61.0 g (1.09 mol) of potassium hydroxide and 500 g of N, N-dimethylformamide were added to the dried reaction product, followed by stirring at 120 DEG C for 8 hours. Next, the mixture was cooled, neutralized to pH 7 with 10% hydrochloric acid solution, extracted with ethyl acetate, and the powder obtained by rotary evaporation was dissolved in 300 mL of tetrahydrofuran , And 32.3 g (0.85 mol) of lithium aluminum hydride were added little by little and reacted. After completion of the reaction, the reaction side product was removed using a water / methanol mixture to obtain a compound represented by the following general formula (8a).

[Chemical Formula 8a]

Figure pat00023

Comparative Synthetic Example  One

50.0 g (0.166 mol) of coronene and 70 g (0.499 mol) of benzoyl chloride were added to 700 g of chloroform / dichlromethane mixed solution to prepare a solution. The solution was stirred using a stirring bar, and 66.6 g (0.499 mol) of aluminum chloride (AlCl 3 , Aluminum Chloride) was added little by little, and then the mixture was heated to 60 ° C and stirred for 8 hours.

After completion of the reaction, methanol was added to precipitate the precipitate, which was then filtered and washed with a water / methanol mixture to remove reaction by-products and unreacted aluminum chloride. 62.5 g (0.102 mol) of the dried reaction product and 200 g of Raney Nickel were stirred with 600 ml of 2-propanol for 1 hour while refluxing. After completion of the reaction, the reaction mixture was cooled to room temperature, and then the organic layer was removed. The reaction mixture was rotary evaporated to obtain a compound represented by the following formula (9).

[Chemical Formula 9]

Figure pat00024

Hard mask  Preparation of composition

Example  One

The compound obtained in Synthesis Example 1 was dissolved in a mixed solvent of propylene glycol monomethyl ether acetate (PGMEA) and cyclohexanone (7: 3 (v / v)), . The content of the compound was adjusted to 10.0% by weight or 13.0% by weight based on the total weight of the hard mask composition, depending on the intended thickness.

Example  2

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

Example  3

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

Example  4

A hard mask composition was prepared in the same manner as in Example 1, except that the monomer obtained in Synthesis Example 4 was used instead of the monomer obtained in Synthesis Example 1.

Example  5

A hard mask composition was prepared in the same manner as in Example 1, except that the monomer obtained in Synthesis Example 5 was used instead of the monomer 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 monomer obtained in Comparative Synthesis Example 1 was used instead of the monomer obtained in Synthesis Example 1.

Evaluation 1: Chemical resistance

A hard mask composition having a monomer content of 10.0% by weight according to Examples 1 to 5 and Comparative Example 1 was applied on a silicon wafer by a spin-on coating method and then heat-treated at 240 DEG C for 1 minute on a hot plate to form a thin film. The initial film thickness was measured with a K-MAC thin film thickness gauge.

Subsequently, the thin film was immersed in a mixed solvent of ethyl 3-ethoxypropionate (EEP) and ethyl lactate (EL) (7: 3 (v / v)) for 1 minute And the thickness of the thin film was measured.

The results are shown in Table 1.

Initial thin film thickness (Å) Thickness (Å) after immersion Thin film thickness reduction rate (%) Example 1 2553 1736 -32 Example 2 2475 2247 -9.2 Example 3 2995 2988 -0.23 Example 4 2821 2660 -5.7 Example 5 2662 2657 -0.19 Comparative Example 1 2680 375 -86

Referring to Table 1, it can be seen that the thin film formed from the hard mask composition according to Examples 1 to 5 has a smaller thickness reduction rate after immersion than the thin film formed from the hard mask composition according to Comparative Example 1. [

From the results, it can be seen that the hard mask composition according to Examples 1 to 5 is sufficiently crosslinked even at a relatively low temperature of 240 ° C as compared with the hard mask composition according to Comparative Example 1 to form a thin film having high chemical resistance have.

Evaluation 2: Heat resistance

On the silicon wafers, 10.0% by weight of monomers according to Examples 1 to 5 and Comparative Example 1 The hard mask composition was applied by a spin-on coating method and then heat-treated at 240 DEG C for 1 minute on a hot plate to form a thin film. The thickness of the thin film was measured with a thin film thickness gauge of K-MAC. Subsequently, the thin film was again heat-treated at 400 ° C for 2 minutes, and then the thickness of the thin film was measured.

On the other hand, outgassing was visually observed at 240 ° C and 400 ° C, respectively.

The results are shown in Table 2.

After 240 ℃ heat treatment
Thin film thickness (Å) After heat treatment at 400 ℃
Thin film thickness (Å) Thin film thickness
Decrease (%) Outgassing
Occurrence Example 1 2603 2160 -17 Not observed Example 2 2422 2248 -7.2 Not observed Example 3 2910 2829 -2.8 Not observed Example 4 2835 2566 -9.5 Not observed Example 5 2701 2606 -3.5 Not observed Comparative Example 1 2668 1841 -31 At 400 ° C
Occur

Referring to Table 2, it can be seen that the thin film formed from the hard mask composition according to Examples 1 to 5 has a smaller thickness reduction rate at the heat treatment at 400 캜 than the thin film formed from the hard mask composition according to Comparative Example 1.

Also, the thin films formed from the hard mask compositions according to Examples 1 to 5 did not cause outgassing even at 400 DEG C, unlike the thin films formed from the hard mask composition according to Comparative Example 1. [

From the results, it can be seen that the hard mask composition according to Examples 1 to 5 has a high heat resistance even at a high temperature of 400 ° C because of the high degree of crosslinking of the thin film as compared with the hard mask composition according to Comparative Example 1.

Rating 3: Awareness of corrosion

A hard mask composition having a monomer content of 13% by weight in accordance with Examples 1 to 5 and Comparative Example 1 was applied on a silicon wafer by a spin-on coating method and then heat-treated at 240 DEG C for 1 minute on a hot plate to form a thin film. The thickness of the thin film was measured with a thin film thickness gauge of K-MAC.

Next, N 2 / O 2 　 After dry etching for 60 seconds using a mixed gas, the thickness of the thin film was measured and the etching rate was calculated therefrom .

The results are shown in Table 3.

Initial thin film thickness (Å) Thickness after etching (Å) The etching rate (Å / sec) Example 1 4525 3055 24.5 Example 2 4351 2941 23.5 Example 3 4792 3406 23.1 Example 4 4295 2897 23.3 Example 5 4777 3403 22.9 Comparative Example 1 4478 2936 25.7

The bulk etch rate (BER)

: (Initial thin film thickness - thin film thickness after etching) / etching time (seconds)

Referring to Table 3, it can be seen that the thin film formed from the hard mask composition according to Examples 1 to 5 has a lower etching rate than the thin film formed from the hard mask composition according to Comparative Example 1. [

From the results, it can be seen that the hard mask composition according to Examples 1 to 5 has higher corrosion resistance due to the high degree of crosslinking of the thin film as compared with the hard mask composition according to Comparative Example 1.

Evaluation 4: Pattern formation

A silicon oxide (SiO 2 ) layer with a thickness of 3,000 Å was formed on a silicon wafer by a chemical vapor deposition method. Next, a hard mask composition having a monomer content of 13.0% by weight in accordance with Examples 1 to 5 and Comparative Example 1 was applied on the silicon oxide layer by a spin-on coating method and then heat-treated at 240 DEG C for 1 minute on a hot plate, . Subsequently, a silicon nitride (SiN) layer was formed on the hard mask layer by a chemical vapor deposition method. Subsequently, the photoresist for KrF was coated and heat-treated at 110 ° C. for 60 seconds, exposed using ASML (XT: 1400, NA 0.93) exposure equipment, and developed with tetramethylammonium hydroxide (2.38 wt% TMAH aqueous solution). Subsequently, the silicon nitride layer was dry-etched using a mixed gas of CHF 3 / CF 4 using the patterned photoresist as a mask. Then, the hard mask layer was dry-etched using a N 2 / O 2 mixed gas using the patterned silicon nitride layer as a mask. Then, the silicon oxide layer was dry-etched using a CHF 3 / CF 4 mixed gas using the patterned hard mask layer as a mask, and then the remaining organic substances were removed using O 2 gas.

Sectional view of the hard mask layer and the silicon oxide layer pattern was observed using an electron microscope (SEM).

The results are shown in Table 4.

Hard mask layer pattern shape Silicon oxide layer pattern shape Example 1 Vertical shape Vertical shape Example 2 Vertical shape Vertical shape Example 3 Vertical shape Vertical shape Example 4 Vertical shape Vertical shape Example 5 Vertical shape Vertical shape Comparative Example 1 Tapered shape Tapered shape

Referring to Table 4, the hard mask layer formed with the hard mask composition according to Examples 1 to 5 and the silicon oxide layer thereunder were all patterned in a vertical shape, while the hard mask layer formed with the hard mask composition according to Comparative Example 1 Is not patterned in a vertical shape and is patterned in a tapered shape.

From this, it was found that when the hard mask composition according to Examples 1 to 5 was used, the material layer having a better etching resistance than that of the hard mask composition according to Comparative Example 1, Pattern. ≪ / RTI >

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 (18)

A monomer for a hard mask composition represented by Formula 1:
[Chemical Formula 1]
Figure pat00025

In Formula 1,
A and A 'are the same or different substituted or unsubstituted aromatic groups,
X, X 'and X "each independently represents a hydroxyl group, a halogen atom, a halogen-containing group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1- A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C7 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy 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 C1 to C4 alkyl A substituted or unsubstituted C7 to C20 arylalkylene ether, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C1 to C20 alkylboranyl group, a substituted or unsubstituted C6 to C30 arylborane group, A combination thereof,
L is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group or a combination thereof,
n is an integer of 1 to 5,
When p is the maximum number of substituents that A can have, k is an integer satisfying 0? k? pn-1,
and q is an integer satisfying 0? m? q-2 when A 'is the maximum number of substituents that A' can have. The method of claim 1,
Wherein A and A 'are each independently a substituted or unsubstituted aromatic group selected from the groups listed in the following Group 1:
[Group 1]
Figure pat00026

In the group 1,
Z 1 represents a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl (O), sulfur (S), or a combination thereof, wherein R is a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, a is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group, a halogen atom,
Z 3 to Z 18 each independently represent C = O, NR a , oxygen (O), sulfur (S), CR b R c Or a combination thereof, wherein each of R a to R c is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group , A halogen atom, a halogen-containing group, or a combination thereof. The method of claim 1,
Wherein at least one of A and A 'is a substituted or unsubstituted polycyclic aromatic group. The method of claim 1,
Wherein the monomer is represented by the following formula (2) or (3):
(2)
Figure pat00027

(3)
Figure pat00028

In the above Formulas 2 and 3,
A 0 to A 3 each independently represent a substituted or unsubstituted benzene group, a naphthalene group, a pyrene group, a benzopyrylene group, a perylene group, a benzoperylene group, a coronene group,
X 1 to X 6 each independently represent a hydroxyl group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a halogen atom, a halogen-containing group, a substituted or unsubstituted C1 to C30 alkoxy group, Substituted C1 to C20 alkylborane, substituted or unsubstituted C6 to C30 arylborane, or combinations thereof. 5. The method of claim 4,
Wherein the monomer is represented by any one of the following formulas (4) to (8):
[Chemical Formula 4]
Figure pat00029

[Chemical Formula 5]
Figure pat00030

[Chemical Formula 6]
Figure pat00031

(7)
Figure pat00032

[Chemical Formula 8]
Figure pat00033
 The method of claim 1,
Wherein the monomer has a molecular weight of from 200 to 5,000. A monomer represented by the following formula (1), and
menstruum
A hard mask composition comprising:
[Chemical Formula 1]
Figure pat00034

In Formula 1,
A and A 'are the same or different substituted or unsubstituted aromatic groups,
X, X 'and X "each independently represents a hydroxyl group, a halogen atom, a halogen-containing group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1- A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C7 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy 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 C1 to C4 alkyl A substituted or unsubstituted C7 to C20 arylalkylene ether, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C1 to C20 alkylboranyl group, a substituted or unsubstituted C6 to C30 arylborane group, A combination thereof,
L is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group or a combination thereof,
n is an integer of 1 to 5,
When p is the maximum number of substituents that A can have, k is an integer satisfying 0? k? pn-1,
and q is an integer satisfying 0? m? q-2 when A 'is the maximum number of substituents that A' can have. 8. The method of claim 7,
Wherein A and A 'are a substituted or unsubstituted aromatic group selected from the groups listed in the following Group 1:
[Group 1]
Figure pat00035

In the group 1,
Z 1 represents a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl (O), sulfur (S), or a combination thereof, wherein R is a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, a is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group, a halogen atom,
Z 3 to Z 18 each independently represent C = O, NR a , oxygen (O), sulfur (S), CR b R c Or a combination thereof, wherein each of R a to R c is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group , A halogen atom, a halogen-containing group, or a combination thereof. 8. The method of claim 7,
Wherein at least one of A and A 'is a substituted or unsubstituted polycyclic aromatic group. 8. The method of claim 7,
Wherein the monomer is represented by Formula 2 or 3:
(2)
Figure pat00036

(3)
Figure pat00037

In the above Formulas 2 and 3,
A 0 to A 3 each independently represent a substituted or unsubstituted benzene group, a naphthalene group, a pyrene group, a benzopyrylene group, a perylene group, a benzoperylene group, a coronene group,
X 1 to X 6 each independently represent a hydroxyl group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a halogen atom, a halogen-containing group, a substituted or unsubstituted C1 to C30 alkoxy group, Substituted C1 to C20 alkylborane, substituted or unsubstituted C6 to C30 arylborane, or combinations thereof. 8. The method of claim 7,
Wherein the monomer is represented by any one of the following formulas (4) to (8):
[Chemical Formula 4]
Figure pat00038

[Chemical Formula 5]
Figure pat00039

[Chemical Formula 6]
Figure pat00040

(7)
Figure pat00041

[Chemical Formula 8]
Figure pat00042
 8. The method of claim 7,
Wherein the monomer has a molecular weight of from 200 to 5,000. 8. The method of claim 7,
Wherein the monomer is included in an amount of from 0.1% to 50% by weight based on the total amount of the hard mask composition. Providing a layer of material over the substrate,
Applying a hard mask composition according to any one of claims 7 to 13 on said material layer,
Heat treating the hard mask 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 > The method of claim 14,
Wherein the step of applying the hard mask composition is performed by a spin-on coating method. The method of claim 14,
Wherein the forming of the hard mask layer is performed at a temperature of 100 ° C to 500 ° C. The method of claim 14,
And forming a bottom anti-reflective layer (BARC) on the silicon-containing thin film layer. The method of claim 17,
Wherein the silicon-containing thin film layer contains silicon oxynitride (SiON).
KR20130073949A 2013-06-26 2013-06-26 Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition KR20150002931A (en)

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* Cited by examiner, † Cited by third party
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