KR20130026912A - Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns - Google Patents

Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns Download PDF

Info

Publication number
KR20130026912A
KR20130026912A KR1020110090368A KR20110090368A KR20130026912A KR 20130026912 A KR20130026912 A KR 20130026912A KR 1020110090368 A KR1020110090368 A KR 1020110090368A KR 20110090368 A KR20110090368 A KR 20110090368A KR 20130026912 A KR20130026912 A KR 20130026912A
Authority
KR
South Korea
Prior art keywords
substituted
unsubstituted
group
layer
hard mask
Prior art date
Application number
KR1020110090368A
Other languages
Korean (ko)
Inventor
김민수
김영민
이철호
이충헌
송지윤
조연진
Original Assignee
제일모직주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 제일모직주식회사 filed Critical 제일모직주식회사
Priority to KR1020110090368A priority Critical patent/KR20130026912A/en
Publication of KR20130026912A publication Critical patent/KR20130026912A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
    • C07C15/62—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing four 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • 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

Landscapes

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

Abstract

A hard mask composition comprising an aromatic ring-containing compound and a solvent comprising a moiety represented by Formula 1, a pattern forming method using the hard mask composition, and a semiconductor integrated circuit device including a pattern formed by the method.
[Formula 1]

Figure pat00025

In formula 1, R1 to R4, X1 and X2, n, n1 to n4 are as defined in the specification.

Description

A hard mask composition, a method of forming a pattern using the same, and a semiconductor integrated circuit device including the pattern, and a semiconductor integrated circuit device including the pattern, and a semiconductor integrated circuit device including the pattern.

A hard mask composition, a pattern forming method using the same, and a semiconductor integrated circuit device including the pattern.

There is a need to reduce the size of patterns to provide larger amounts of circuitry for a given chip size, as well as in microelectronics as well as in the fabrication of microscopic structures (eg, micromachines, magnetoresist heads, etc.). .

Effective lithographic techniques are essential to achieving a reduction in pattern size. Lithographic influences the fabrication of microscopic structures not only in terms of directly imaging the pattern on a given substrate, but also in the manufacture of masks typically used for such imaging.

Typical lithographic processes include forming a patterned resist layer by patterning exposing the radiation-sensitive resist to imaging radiation. The exposed resist layer is then developed with a developer. 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 effectively transfer the desired pattern to the layer behind the resist. Thus, for example, when an ultra thin resist layer is required, when the backing material to be etched is thick, when a considerable etching depth is required and / or when it is necessary to use a specific etchant for a given backing material, The hardmask layer is used as an intermediate layer between the resist layer and the backing material that can be patterned by transfer from the patterned resist.

The hardmask layer must be able to withstand the etching process needed to receive the pattern from the patterned resist layer and transfer the pattern to the backing material.

It is desirable to perform lithographic techniques using hardmask compositions that have high etch selectivity, sufficient resistance to multiple etching, and minimize reflectivity between resist and backing layers. Patterns using such hardmask compositions may have improved optical properties.

Such hard mask compositions can be used in a dual damascene process.

The dual damascene process can be broadly divided into trench-first dual damascene (TFDD), via-first dual damascene (VFDD), and hardmask dual damascene (HMDD), depending on the patterning method. Among these, the VFDD process also requires gap-fill characteristics and planarization characteristics in addition to the above-described etching and optical characteristics.

One embodiment provides a hardmask composition that is excellent in gapfill and planarization properties while improving etch resistance and optical properties.

Another embodiment provides a method of forming a pattern using the hard mask composition.

Yet another embodiment provides a semiconductor integrated circuit device comprising a pattern formed by the above method.

According to one embodiment, there is provided a hard mask composition comprising an aromatic ring-containing compound and a solvent comprising a moiety represented by the following Chemical Formula 1.

[Formula 1]

Figure pat00001

In Formula 1,

R 1 , R 3 and R 4 are each independently hydrogen, a hydroxy group, a halogen 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 , Substituted or unsubstituted C3 to C30 cycloalkenyl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted A substituted 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 substituted or One selected from an unsubstituted siloxane group, a substituted or unsubstituted silane group, and a combination thereof,

R 2 is hydrogen, a halogen 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 C3 to C30 cycloalke 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, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted C1 to C20 aldehyde group, substituted or unsubstituted amino group, substituted or unsubstituted siloxane group, substituted or unsubstituted One selected from a silane group and a combination thereof,

n 1 to n 4 are each independently an integer of 0 to 2,

n is 2 to 10,

X 1 and X 2 are each independently 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 C3 to C30 cycloalkenylene group, substituted or unsubstituted C7 to C20 arylalkylene group, substituted or unsubstituted C1 to C20 heteroalkylene group, substituted or unsubstituted C2 to C30 heterocycloalkylene group, substituted or unsubstituted C2 to C30 heteroarylene group, substituted or unsubstituted C2 to C30 alkenylene group, substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof.

X 1 and X 2 may be each independently selected from a substituted or unsubstituted linking group listed in Group 1 below.

[Group 1]

Figure pat00002

R 5 to R 49 are each independently hydrogen, a hydroxy group, a halogen 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 an unsubstituted C3 to 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 One selected from a 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, and a combination thereof.

Formula 1 may include at least one selected from compounds represented by Formulas 1a to 1c.

[Formula 1a]

Figure pat00003

[Chemical Formula 1b]

Figure pat00004

[Chemical Formula 1c]

Figure pat00005

In Chemical Formulas 1a to 1c, n is 2 to 10.

The aromatic ring-containing compound may have a weight average molecular weight of about 100 to 100,000.

The aromatic ring-containing compound may have a weight average molecular weight of about 1,000 to 30,000.

The aromatic ring-containing compound may be included in about 1 to 20 parts by weight based on 100 parts by weight of the solvent.

According to another embodiment, there is provided a method of manufacturing a semiconductor device, comprising: providing a material layer on a substrate; applying the hard mask composition described above to the material layer to form a hard mask layer; Selectively exposing a portion of the material layer using the resist pattern, and etching the exposed portion of the material layer to expose a portion of the material layer, The method comprising the steps of:

The forming of the hard mask layer may be performed by a spin-on-coating method.

The method of forming a pattern may further include forming an auxiliary layer containing silicon on the material layer before forming the resist layer.

The pattern forming method may further include forming a bottom anti-reflective layer BARC before forming the hard mask layer.

According to another embodiment, a semiconductor integrated circuit device including a plurality of patterns formed by the pattern forming method described above is provided.

It can increase the gap fill characteristics and planarization characteristics while securing optical characteristics and improving resistance to multiple etching.

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 a compound is a halogen atom (F, Br, Cl, or I), a hydroxyl group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amino group Dino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, alkyl group, C2 to C20 alkenyl group, C2 to C20 Alkynyl group, C6 to C30 aryl group, C7 to C30 arylalkyl group, C1 to C4 alkoxy group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, C3 to C30 cycloalkyl group, C3 to C15 cycloalkenyl group, C6 to C15 It means substituted with a substituent selected from a cycloalkynyl group, a C2 to C20 heterocycloalkyl group, and a combination thereof.

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

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

The hardmask composition according to one embodiment includes an aromatic ring containing compound and a solvent.

The aromatic ring-containing compound includes a moiety represented by the following formula (1).

[Formula 1]

Figure pat00006

R 1 , R 3 and R 4 are each independently hydrogen, a hydroxy group, a halogen 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 Groups, substituted or unsubstituted C3 to C30 cycloalkenyl groups, substituted or unsubstituted C7 to C20 arylalkyl groups, substituted or unsubstituted C1 to C20 heteroalkyl groups, substituted or unsubstituted C2 to C30 heterocycloalkyl groups, substituted or Unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted C1 to C20 aldehyde group, substituted or unsubstituted amino group, substituted Or an unsubstituted siloxane group, a substituted or unsubstituted silane group, and a combination thereof.

R 2 is hydrogen, a halogen 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 C3 to C30 cyclo Alkenyl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted Or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted C1 to C20 aldehyde group, substituted or unsubstituted amino group, substituted or unsubstituted siloxane group, substituted or unsubstituted Silane group and a combination thereof.

Since R 2 is selected from the substituents listed above, polymerization may occur in various directions as compared to the case where R 2 is a hydroxy group, which is advantageous for forming a mesh type polymer. Accordingly, the degree of crosslinking can be increased to improve the etching resistance, to be polymerized at a relatively low temperature, to increase solubility, and to increase stability at a high temperature.

n 1 to n 4 are each independently an integer of 0 to 2, and n is 2 to 10.

X 1 and X 2 are each independently 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 C3 to C30 cycloalkenylene group, substituted or unsubstituted C7 to C20 arylalkylene group, substituted or unsubstituted C1 to C20 heteroalkylene group, substituted or unsubstituted C2 to C30 heterocycloalkylene group, substituted or unsubstituted C2 to C30 heteroarylene group, substituted or unsubstituted C2 to C30 alkenylene group, substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof.

X 1 and X 2 are each independently a C1 to C30 alkylene group or a substituted or unsubstituted C6 to C30 arylene group.

X 1 and X 2 may be selected from, for example, substituted or unsubstituted linking groups listed in Group 1 below.

[Group 1]

Figure pat00007

R 5 to R 49 are each independently hydrogen, a hydroxy group, a halogen 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 an unsubstituted C3 to 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 One selected from a 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, and a combination thereof.

The aromatic ring-containing compound may absorb light in a predetermined wavelength region, and the light in the predetermined wavelength region may be, for example, a short wavelength region of about 193 nm or 243 nm.

The aromatic ring-containing compound may include two or more aromatic ring-containing compounds having different substituents in the form of a mixture.

The weight average molecular weight of the aromatic ring-containing compound may be about 100 to 100,000. Within this range, the weight average molecular weight of the aromatic ring-containing compound may be about 1,000 to 30,000, and particularly, about 1,500 to 2,100. By having a weight average molecular weight in the above range can have excellent gap fill characteristics and planarization characteristics and can ensure the solubility to implement the desired coating thickness.

The solvent is not particularly limited as long as it has sufficient solubility or dispersibility in the aromatic ring-containing compound, for example, propylene glycol, propylene glycol diacetate, methoxy propanediol, diethylene glycol, diethylene glycol butyl ether, tri (ethylene Glycol) monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, ethyl lactate, gamma-butyrolactone and at least one selected from acetylacetone.

The aromatic ring-containing compound may be included in about 1 to 20 parts by weight based on 100 parts by weight of the solvent. Within this range, the aromatic ring-containing compound may be included in an amount of about 5 to 15 parts by weight based on 100 parts by weight of the solvent. By including the aromatic ring-containing compound in the above range, it is possible to improve the optical properties while securing the coating properties.

The hard mask composition may further include additives such as a surfactant, an acid catalyst, a sulfonate, and a crosslinking agent.

The surfactant may be, for example, alkylbenzenesulfonic acid salt, alkylpyridinium salt, polyethylene glycol, quaternary ammonium salt and the like, 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. Thermal acid generators are acid generators that release acids upon thermal treatment, such as pyridinium p-toluene sulfonate, 2,4,4,6-tetrabromocyclohexadienone, benzointosylate, 2-nitrobenzyl Tosylate, alkyl esters of euphonic acid, and the like.

The crosslinking agent is capable of crosslinking the repeating units of the polymer by heating in the presence of the acid catalyst, an amino resin such as etherified amino resin; A glycoluril compound such as a compound represented by the following formula (A); Bisepoxy compounds, such as a compound represented by following formula (B); Melamine or derivatives thereof such as N-methoxymethyl melamine, N-butoxymethyl melamine or melamine derivatives represented by the following general formula (C); Or a mixture thereof.

(A)

Figure pat00008

[Formula B]

Figure pat00009

≪ RTI ID = 0.0 &

Figure pat00010

The surfactant, acid catalyst,, and crosslinking agent may be included in an amount of about 0.001 to 3 parts by weight, respectively, based on 100 parts by weight of the hard mask composition. By including in the above range, solubility and crosslinkability can be ensured without changing the optical properties of the hard mask composition.

Hereinafter, the method of forming a pattern using the hard mask composition mentioned above is demonstrated.

According to one or more exemplary embodiments, a method of forming a pattern includes: providing a material layer on a substrate, applying a hard mask composition including the aromatic ring-containing compound and a solvent on the material layer to form a hard mask layer, and the hard mask. Forming a resist layer over the layer, exposing and developing the resist layer to form a resist pattern, selectively removing the hardmask layer 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 can be formed, for example, by chemical vapor deposition.

The hard mask layer may be formed by applying a hard mask composition.

The hard mask composition is as described above.

The hardmask composition may be prepared in a solution form and applied by a spin-on-coating method. Subsequently, the applied hard mask composition is heat treated to form a hard mask layer.

At this time, the coating thickness, heat treatment conditions, etc. of the hard mask composition is not particularly limited, but may be applied, for example, to a thickness of about 500 to 10,000 Pa, and may be heat treated, for example, at about 100 to 300 ° C. for 10 seconds to 10 minutes.

Another auxiliary layer may be further formed before the hard mask layer is formed. In this case, the auxiliary layer may be a silicon-containing thin film, for example, a thin film made of silicon nitride or silicon oxide.

In addition, a bottom anti-reflective coating (BARC) may be further formed before forming the auxiliary layer.

Subsequently, a resist layer is applied on the hard mask layer. The resist layer may be a radiation-sensitive imaging layer that includes a photosensitive material.

The resist layer is then exposed and developed to form a resist pattern. At this time, the exposure can be performed using, for example, ArF, KrF or E-beam. In addition, a baking process may be performed at about 150 to 500 ° C. after exposure.

Subsequently, the hard mask layer is selectively removed using the resist pattern as a mask. In this case, when the auxiliary layer and / or the bottom antireflection layer are formed, these may be removed together. This may expose a portion of the underlying material layer.

The exposed portion of the material layer is then etched. In this case, the etching may be performed by dry etching using an etching gas, and the etching gas may use, for example, CHF 3 , CF 4 , CH 4 , Cl 2 , BCl 3, and a mixed gas thereof.

The hardmask layer, resist layer and the like are then removed using a conventional stripper to form a plurality of patterns formed from the material layer.

The plurality of patterns may vary from metal patterns, semiconductor patterns, insulating patterns, and the like, and may be various patterns in a semiconductor integrated circuit device. A metal wiring when the pattern is included in a semiconductor integrated circuit device; Semiconductor pattern; A contact hole, a bias hole, a damascene trench, or the like.

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.

Synthesis of Aromatic Ring-containing Compounds

Synthetic example  One

After preparing a 500 ml three-necked flask equipped with a thermometer, a condenser and a mechanical stirrer, the three-necked flask was immersed in an oil thermostat at 90 to 100 ° C. The thermostat was placed on a hot plate and stirred using a stirring bar while maintaining the constant temperature. At this time, the cooling water temperature of the condenser was fixed at 5 ° C.

Subsequently, 28.83 g (0.2 mol) of 1-naphthol, 28.32 g (0.14 mol) of pyrene and 12.0 g (0.34 mol) of paraformaldehyde were added to the three neck flask. Subsequently, 0.19 g (1 mmol) of p-toluene sulfonic acid monohydrate was dissolved in 162 g of propylene glycol monomethyl ether acetate (PGMEA), and the solution was added to the three neck flask. 　 The reaction was carried out by stirring for 5 to 12 hours. 　

Samples were taken from the polymerization reactant at 1 hour intervals, and the weight average molecular weight of the sample was measured to complete the reaction when the weight average molecular weight was 1,800 to 2,500. At this time, the weight average molecular weight of the sample prepared by taking 1g of the sample from the polymerization reaction and quenching to room temperature, 0.02g of which was diluted by using tetrahydrofuran (THF) as a solvent to 4% by weight solids Was measured.

polymerization 　 After the reaction was completed, the reaction was slowly cooled to room temperature.

The reactant was poured into 40 g of distilled water and 400 g of methanol, and stirred vigorously, followed by standing still. The supernatant was removed, and the precipitate was dissolved in 80 g of propylene glycol monomethyl ether acetate (PGMEA), followed by vigorous stirring using 320 g of methanol, followed by standing (primary). The resulting supernatant was again removed and the precipitate was dissolved in 80 g of propylene glycol monomethyl ether acetate (PGMEA) (second order). The first and second processes were referred to as one-time purification processes, and this purification process was carried out three times in total. The purified polymer was dissolved in 80 g of propylene glycol monomethyl ether acetate (PGMEA), and methanol and distilled water remaining in the solution were removed under reduced pressure.

The aromatic ring containing compound represented by following General formula (1a) was obtained.

[Formula 1a]

Figure pat00011

The weight average molecular weight of the aromatic ring-containing compound was 2,085, and the polydispersity was 1.33.

Synthetic example  2

Except for using 28.32 g (0.14 mol) of pyrene, 44.02 g (0.14 mol) of 1,1-cyclohexyl pyrenyl methanol was used in the same manner as in Synthesis Example 1 to obtain an aromatic ring-containing compound represented by Chemical Formula 1b Got it.

[Chemical Formula 1b]

Figure pat00012

The weight average molecular weight of the aromatic ring-containing compound was 2,100 and the dispersion degree was 1.38.

Synthetic example  3

Aromatic ring-containing compounds represented by the following Chemical Formula 1c were obtained by the same method as Synthesis Example 1, except that 36.45 g (0.14 mol) of 1,1-ethyl pyrenyl methanol was used instead of 28.32 g (0.14 mol) of pyrene. .

[Chemical Formula 1c]

Figure pat00013

The weight average molecular weight of the aromatic ring-containing compound was 2,150 and the dispersion degree was 1.39.

Comparative Synthetic Example  One

After preparing a 500 ml three-necked flask equipped with a thermometer, a capacitor, and a mechanical stirrer, the three-necked flask was immersed in an oil thermostat at 140 ° C. The thermostat was placed on a hot plate and stirred using a stirring bar while maintaining the constant temperature. At this time, the cooling water temperature of the condenser was fixed at 40 ° C.

Subsequently, 220 g (1 mol) of 1-methoxypyrene and 138 g (1 mol) of 1,4-bismethoxymethylbenzene were dissolved in 656 g of propylene glycol monomethyl ether acetate (PGMEA) in the three-necked flask. To this solution was then added 4.6 g (0.03 mol) of diethylsulfate.

While maintaining the temperature of the reactor at 130 ℃ sample is taken from the polymerization reaction at intervals of 1 hour to measure the weight average molecular weight of the sample. The weight average molecular weight is measured with a sample prepared by taking 1 g of a sample from the polymerization reactant, quenching it to room temperature, and then diluting it to 4 wt% by using 0.02 g of which is tetrahydrofuran (THF) as a solvent. It was.

polymerization 　 After the reaction was completed, the reaction was slowly cooled to room temperature.

The reaction was diluted with 500 g of propylene glycol monomethyl ether acetate (PGMEA). Subsequently, 4 kg of a methanol: ethylene glycol mixed solvent mixed in a 90:10 weight ratio was prepared, and the synthesized solution was added dropwise to the mixed solvent under vigorous stirring. The resulting polymer was collected at the bottom of the flask and the supernatant was stored separately. After removing the supernatant, rotary evaporation was carried out under reduced pressure at 60 ° C. for 10 minutes to obtain an aromatic ring-containing compound represented by the following Chemical Formula 1d.

≪ RTI ID = 0.0 &

Figure pat00014

The weight average molecular weight of the aromatic ring-containing compound was 4,000, and the dispersion degree was 2.3.

Comparative Synthetic Example  2

After preparing a 2,000 ml three-necked flask equipped with a thermometer, a condenser, a mechanical stirrer and a dropping funnel, the three-necked flask was immersed in an oil thermostat at 140 ° C. This thermostat was put on the hotplate, and it stirred using the stirring magnet. At this time, the cooling water temperature of the condenser was fixed at 40 ° C.

Subsequently, 65.48 g (1 mol) of 1-hydroxypyrene and 103.12 g (1 mol) of 9,9'-bis (phenol) fluorene were added to the three neck flask. 270.34 g of propylene glycol monomethyl ether acetate (PGMEA) was added thereto and dissolved. 4.62 g (0.05 mol) of diethyl sulfate was then added to the obtained product.

199.48 g (2.0 mol) of 1.4-bismethoxymethylbenzene was added to the dropping funnel, and when the temperature of the three-necked flask reached 130 ° C, the 1.4-bismethoxymethylbenzene was added to the three-necked flask over 1.5 hours. Added slowly.

Samples were taken from the polymerization reactant at 1 hour intervals, and the weight average molecular weight of the sample was measured to complete the reaction when the weight average molecular weight was 2,500 to 3,500. At this time, the weight average molecular weight of the sample prepared by taking 1g of the sample from the polymerization reaction and quenching to room temperature, 0.02g of which was diluted by using tetrahydrofuran (THF) as a solvent to 4% by weight solids Was measured.

At the completion of the reaction, 4.48 g (0.03 mol) of triethanolamine was added to the three-necked flask as a neutralizing agent and stirred to terminate the reaction. The reaction was then slowly cooled to room temperature.

The reaction was diluted with 500 g of propylene glycol monomethyl ether acetate (PGMEA) to prepare a polymer solution. Thereafter, the polymer solution was added to 2,000 ml of a separatory funnel, and 4 kg of a mixed solvent of methanol and ethylene glycol (90:10 g / g) was added dropwise with vigorous stirring.

That 　 As a result, the polymer was collected at the bottom of the flask, and the supernatant was separated and stored separately. After removing the supernatant, rotary evaporation was carried out at 60 ° C. for 10 minutes to remove methanol from the final reaction product, thereby obtaining an aromatic ring-containing compound represented by Chemical Formula 1e.

[Formula 1e]

Figure pat00015

The weight average molecular weight of the aromatic ring-containing compound was 12,000, and the dispersion degree was 2.3.

Comparative Synthetic Example  3

After preparing a 2,000 ml three-necked flask equipped with a thermometer, a condenser, a mechanical stirrer, and a dropping funnel, the three-necked flask was immersed in an oil bath at 65 ° C. This thermostat was put on the hotplate, and it stirred using the stirring magnet. At this time, the cooling water temperature of the condenser was fixed at 30 ° C.

Subsequently, 61.11 g (1 mol) of 1-hydroxypyrene and 20.18 g (0.5 mol) of 2-naphthol and 12.61 g (1.5 mol) of paraformaldehyde were added to the three neck flask. 219.74 g of propylene glycol monomethyl ether acetate (PGMEA) was added and dissolved therein. 0.267 g (0.050 mol) of paratoluene sulfonic acid was then added to the obtained product.

Samples were taken from the polymerization reactant at 1 hour intervals, and the weight average molecular weight of the sample was measured to complete the reaction when the weight average molecular weight was 1,900 to 2,100. At this time, the weight average molecular weight of the sample prepared by taking 1g of the sample from the polymerization reaction and quenching to room temperature, 0.02g of which was diluted by using tetrahydrofuran (THF) as a solvent to 4% by weight solids Was measured.

The reaction was diluted with 500 g of propylene glycol monomethyl ether acetate (PGMEA) to prepare a polymer solution. Thereafter, the polymer solution was added to 2,000 ml of a separatory funnel, and 4 kg of a mixed solvent of methanol and ethylene glycol (90:10 g / g) was added dropwise with vigorous stirring.

That 　 As a result, the polymer was collected at the bottom of the flask, and the supernatant was separated and stored separately. After removing the supernatant, rotary evaporation was carried out at 60 ° C. for 10 minutes to remove methanol from the final reaction product, thereby obtaining an aromatic ring-containing compound represented by Chemical Formula 1f.

(1f)

Figure pat00016

The weight average molecular weight of the aromatic ring-containing compound was 2,500, and the degree of dispersion was 1.83.

Comparative Synthetic Example  4

A reaction ring containing 95.degree. C. and 36.45 g (0.2 mol) of 1-naphthol and 12.61 g (1.5 mol) of paraformaldehyde were added to obtain an aromatic ring-containing compound represented by the following Chemical Formula 1g in the same manner as in Synthesis Example 1.

[Formula 1g]

Figure pat00017

The weight average molecular weight of the aromatic ring-containing compound was 2,000, and the dispersion degree was 1.38.

Hard mask  Preparation of the composition

Example  One

0.8 g of the aromatic ring-containing compound obtained in Synthesis Example 1, 0.2 g of glycoluril derivative crosslinker represented by the following formula (A) and 2 mg of pyridinium p-toluene sulfonate were dissolved in 9 g of propylene glycol monomethyl ether acetate (PGMEA). After filtration to prepare a hard mask composition.

(A)

Figure pat00018

Example  2

A hardmask composition was prepared in the same manner as in Example 1, except that the aromatic ring-containing compound obtained in Synthesis Example 2 was used instead of the aromatic ring-containing compound obtained in Synthesis Example 1.

Example  3

A hardmask composition was prepared in the same manner as in Example 1, except that the aromatic ring-containing compound obtained in Synthesis Example 3 was used instead of the aromatic ring-containing compound obtained in Synthesis Example 1.

Comparative example  One

A hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Comparative Synthesis Example 1 was used instead of the aromatic ring-containing compound obtained in Synthesis Example 1.

Comparative example  2

A hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Comparative Synthesis Example 2 was used instead of the aromatic ring-containing compound obtained in Synthesis Example 1.

Comparative example  3

A hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Comparative Synthesis Example 3 was used instead of the aromatic ring-containing compound obtained in Synthesis Example 1.

Comparative example  4

A hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Comparative Synthesis Example 4 was used instead of the aromatic ring-containing compound obtained in Synthesis Example 1.

Hard mask  Formation of layers

The hard mask composition according to Examples 1 to 3 was applied on the silicon wafer on which silicon nitride was formed by spin coating, and then baked at 240 ° C. for 60 seconds to form a hard mask layer having a thickness of about 3,000 mm 3.

Rating-1

The refractive index (n) and extinction coefficient (k) of the hard mask layer formed of the hard mask compositions according to Examples 1 to 3 were measured. The refractive index and the extinction coefficient were measured using an Ellipsometer (manufactured by J.A. Woollam) while irradiating 193 nm and 248 nm light, respectively.

The results are shown in Table 1.

Optical Characteristic (193nm) Optical properties (248 nm) Refractive index (n) Absorption coefficient (k) Refractive index (n) Absorption coefficient (k) Example 1 1.40 0.52 2.02 0.61 Example 2 1.38 0.45 2.01 0.55 Example 3 1.36 0.48 2.00 0.58

Referring to Table 1, it can be seen that the hard mask layer formed of the hard mask composition according to Examples 1 to 3 exhibits refractive index (n) and extinction coefficient (k) suitable for use as a hard mask layer for 193 nm and 248 nm light. Can be.

Resist  Formation of patterns

After applying the hard mask composition according to Examples 1 to 3 and Comparative Examples 1 to 4 on the silicon wafer on which silicon nitride is formed by spin coating, baking at 240 ° C. for 60 seconds to form a hard mask layer having a thickness of about 5,000 μs. It was.

The KrF resist was applied on the hard mask layer and baked at 110 ° C. for 60 seconds, and then exposed using KrML exposure equipment ASML (XT: 1400, NA0.93). Subsequently, it was developed with a 2.38wt% aqueous solution of tetramethylammonium hydroxide (TMAH) to form a resist pattern.

Rating-2

The exposure latitude (EL) margin and the depth of focus (DoF) margin due to the variation of the distance between the light source and the light exposure are discussed. In addition, FE-SEM was used to observe whether an undercut occurred in the patterned hard mask layer.

The results are shown in Table 2.

EL margin
(△ CD / exposure energy, mJ) DoF margin (μm) Undercut occurrence Example 1 0.5 0.6 X Example 2 0.4 0.5 X Example 3 0.4 0.4 X Comparative Example 1 0.3 0.3 X Comparative Example 2 0.3 0.1 X Comparative Example 3 0.2 0.3 X Comparative Example 4 0.4 0.2 X

Referring to Table 2, it can be seen that the hard mask layer formed of the hard mask composition according to Examples 1 to 3 has a higher EL margin and a DoF margin than the hard mask layer formed of the hard mask composition according to Comparative Examples 1 to 4. Can be. In addition, it can be seen that the hard mask layer formed of the hard mask composition according to Examples 1 to 3 was formed with a good profile without an undercut observed.

Formation of patterns

The silicon nitride was dry etched using the CHF 3 / CF 4 mixed gas using the patterned hard mask layer as a mask, and then dry etched once more using the BCl 3 / Cl 2 mixed gas. The remaining organics were then removed using O 2 gas.

Evaluation-3

FE-SEM was used to examine the pattern of the hard mask layer and the silicon nitride. The results are shown in Table 3.

Pattern shape Example 1 Anisotropic Example 2 Anisotropic Example 3 Anisotropic Comparative Example 1 Tapered shape Comparative Example 2 Tapered shape, rough surface Comparative Example 3 Tapered shape Comparative Example 4 Tapered shape, rough surface

Referring to Table 3, the hard mask layer formed of the hard mask composition according to Examples 1 to 3 and the silicon nitride underneath are all patterned in a vertical shape, while the hard mask layer formed of the hard mask composition according to Comparative Examples 1 to 4 And it can be seen that the silicon nitride of the lower portion is not patterned in a vertical shape, but a tapered shape appears.

This is because when the hard mask composition according to Examples 1 to 3 is used, the etching is performed well because the resistance to the etching gas is sufficient, whereas when the hard mask composition according to Comparative Examples 1 to 4 is used, the resistance to the etching gas is insufficient. Therefore, it is judged that the etching selectivity for patterning the silicon nitride into a good shape is insufficient.

Evaluation-4

After applying the hard mask compositions according to Examples 1 to 3 and Comparative Examples 1 to 4 on the patterned wafer and undergoing a baking process, gap fill and planarization characteristics were observed using a V-SEM apparatus.

The gap fill characteristics were determined by the presence of voids by observing the pattern cross section with an electron scanning microscope (SEM), and the planarization characteristics were quantified by the following formula (1).

The flattening characteristics are excellent as the difference between h1 and h2 is not large, and the smaller the number, the better the flattening characteristics.

[formula]

Figure pat00019

The results are shown in Table 4.

Planarization and Gap-Pill Properties Left Center Right Gap Fill Characteristics Comparative Example 1 94.38 93.19 94.47 With void Comparative Example 2 96.35 95.71 96.39 With void Comparative Example 3 86.44 86.67 86.81 With void Comparative Example 4 88.27 88.77 88.26 With void Example 1 12.05 11.80 11.95 No void Example 2 13.38 13.10 13.67 No void Example 3 13.21 13.01 13.13 No void

Referring to Table 4, when the hard mask composition according to Examples 1 to 3 was used, it was found that the leveling degree was excellent by maintaining almost similar heights at the left, middle, and right sides, and voids were not observed, so that the gapfill characteristics were not observed. It can be seen that it is excellent. On the contrary, when the hard mask compositions according to Comparative Examples 1 to 4 were used, the degree of planarization and the gap-fill characteristics were poor.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements of those skilled in the art using the basic concepts of the present invention defined in the following claims are also provided. It belongs to the scope of the invention.

Claims (11)

A hard mask composition comprising an aromatic ring-containing compound and a solvent comprising a moiety represented by Formula 1 below:
[Formula 1]
Figure pat00020

In Chemical Formula 1,
R 1 , R 3 and R 4 are each independently hydrogen, a hydroxy group, a halogen 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 , Substituted or unsubstituted C3 to C30 cycloalkenyl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted A substituted 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 substituted or One selected from an unsubstituted siloxane group, a substituted or unsubstituted silane group, and a combination thereof,
R 2 is hydrogen, a halogen 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 C3 to C30 cycloalke 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, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted C1 to C20 aldehyde group, substituted or unsubstituted amino group, substituted or unsubstituted siloxane group, substituted or unsubstituted One selected from a silane group and a combination thereof,
n 1 to n 4 are each independently an integer of 0 to 2,
n is 2 to 10,
X 1 and X 2 are each independently 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 C3 to C30 cycloalkenylene group, substituted or unsubstituted C7 to C20 arylalkylene group, substituted or unsubstituted C1 to C20 heteroalkylene group, substituted or unsubstituted C2 to C30 heterocycloalkylene group, substituted or unsubstituted C2 to C30 heteroarylene group, substituted or unsubstituted C2 to C30 alkenylene group, substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof.
In claim 1,
Wherein X 1 and X 2 are each independently selected from substituted or unsubstituted linking groups listed in Group 1 below:
[Group 1]
Figure pat00021

R 5 to R 49 are each independently hydrogen, a hydroxy group, a halogen 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 an unsubstituted C3 to 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 One selected from a 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, and a combination thereof.
In claim 1,
Formula 1 is a hard mask composition comprising at least one selected from compounds represented by Formulas 1a to 1c:
[Formula 1a]
Figure pat00022

[Chemical Formula 1b]
Figure pat00023

[Chemical Formula 1c]
Figure pat00024

 In claim 1,
The aromatic ring-containing compound has a weight average molecular weight of 100 to 100,000 hard mask composition.
5. The method of claim 4,
The aromatic ring-containing compound has a weight average molecular weight of 1,000 to 30,000 hard mask composition.
In claim 1,
The aromatic ring-containing compound is contained in 1 to 20 parts by weight based on 100 parts by weight of the solvent.
Providing a layer of material over the substrate,
Applying a hardmask composition according to any one of claims 1 to 6 on the material layer to form a hardmask layer,
Forming a resist layer on the hardmask layer,
Exposing and developing the resist layer to form a resist pattern,
Selectively removing the hardmask layer and exposing a portion of the material layer using the resist pattern, and
Etching the exposed portion of the material layer
Pattern forming method comprising a.
In claim 7,
Forming the hard mask layer is a pattern forming method performed by a spin-on-coating method.
In claim 7,
Before the step of forming the resist layer
And forming an auxiliary layer containing silicon over said material layer.
In claim 7,
Before forming the hardmask layer
And forming a bottom antireflective layer (BARC).
A semiconductor integrated circuit device comprising a plurality of patterns formed by the pattern forming method according to claim 7.
KR1020110090368A 2011-09-06 2011-09-06 Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns KR20130026912A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020110090368A KR20130026912A (en) 2011-09-06 2011-09-06 Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020110090368A KR20130026912A (en) 2011-09-06 2011-09-06 Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns

Publications (1)

Publication Number Publication Date
KR20130026912A true KR20130026912A (en) 2013-03-14

Family

ID=48178040

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020110090368A KR20130026912A (en) 2011-09-06 2011-09-06 Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns

Country Status (1)

Country Link
KR (1) KR20130026912A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150082982A (en) 2014-01-08 2015-07-16 에스케이씨 주식회사 Solvent for treating aromatic polymer and method of fabricating semiconductor device
US9371444B2 (en) * 2014-05-16 2016-06-21 Samsung Sdi Co., Ltd. Hardmask composition and method of forming patterns using the hardmask composition
KR20160145480A (en) * 2015-06-10 2016-12-20 삼성에스디아이 주식회사 Polymer, organic layer composition, organic layer, and method of forming patterns
US9564325B2 (en) 2013-10-14 2017-02-07 Samsung Electronics Co., Ltd. Methods of fabricating a semiconductor device
US9568825B2 (en) 2014-07-15 2017-02-14 Samsung Sdi Co., Ltd. Hardmask composition and method of forming patterns using the hardmask composition
US9676892B2 (en) 2015-03-10 2017-06-13 Samsung Electronics Co., Ltd. Polymers for hard masks, hard mask compositions including the same, and methods for forming a pattern of a semiconductor device using a hard mask composition
US9862668B2 (en) 2014-11-24 2018-01-09 Samsung Sdi Co., Ltd. Monomer, polymer, organic layer composition, organic layer, and method of forming patterns
US10353292B2 (en) 2015-12-16 2019-07-16 Samsung Sdi Co., Ltd. Polymer, organic layer composition, and method of forming patterns
US10364221B2 (en) 2015-07-06 2019-07-30 Samsung Sdi Co., Ltd. Monomer, organic layer composition, organic layer, and method of forming patterns
KR20200082483A (en) * 2018-12-28 2020-07-08 삼성에스디아이 주식회사 Polymer and hardmask composition and method of forming patterns

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9564325B2 (en) 2013-10-14 2017-02-07 Samsung Electronics Co., Ltd. Methods of fabricating a semiconductor device
KR20150082982A (en) 2014-01-08 2015-07-16 에스케이씨 주식회사 Solvent for treating aromatic polymer and method of fabricating semiconductor device
US9371444B2 (en) * 2014-05-16 2016-06-21 Samsung Sdi Co., Ltd. Hardmask composition and method of forming patterns using the hardmask composition
US9568825B2 (en) 2014-07-15 2017-02-14 Samsung Sdi Co., Ltd. Hardmask composition and method of forming patterns using the hardmask composition
US9862668B2 (en) 2014-11-24 2018-01-09 Samsung Sdi Co., Ltd. Monomer, polymer, organic layer composition, organic layer, and method of forming patterns
US9676892B2 (en) 2015-03-10 2017-06-13 Samsung Electronics Co., Ltd. Polymers for hard masks, hard mask compositions including the same, and methods for forming a pattern of a semiconductor device using a hard mask composition
KR20160145480A (en) * 2015-06-10 2016-12-20 삼성에스디아이 주식회사 Polymer, organic layer composition, organic layer, and method of forming patterns
US10364221B2 (en) 2015-07-06 2019-07-30 Samsung Sdi Co., Ltd. Monomer, organic layer composition, organic layer, and method of forming patterns
US10353292B2 (en) 2015-12-16 2019-07-16 Samsung Sdi Co., Ltd. Polymer, organic layer composition, and method of forming patterns
KR20200082483A (en) * 2018-12-28 2020-07-08 삼성에스디아이 주식회사 Polymer and hardmask composition and method of forming patterns

Similar Documents

Publication Publication Date Title
KR101423171B1 (en) Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns
KR101344792B1 (en) Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns
KR101432605B1 (en) Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns
KR101413069B1 (en) Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition
KR101852460B1 (en) Polymer, organic layer composition, and method of forming patterns
TWI405788B (en) Hardmask composition having antireflective properties and method of patterning material using the same
KR20130026912A (en) Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns
KR100950318B1 (en) Polymer having aromatic rings, hardmask composition with anti-reflective property, and method of patterning materials using the same
KR101566533B1 (en) Hardmask composition and method of forming patterns using the hardmask composition
KR101344788B1 (en) Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns
KR101344793B1 (en) Hardmask composition and method of forming patterns and semiconductor integrated circuit device including the patterns
KR101655394B1 (en) Resist underlayer composition, method of forming patterns and semiconductor integrated circuit device including the patterns
KR20080107210A (en) Hardmask composition having antireflective property and method of patterning materials using the same
KR20110053136A (en) Polymer for under-layer of resist, polymer composition, under-layer composition of resist, of patterning device using same
KR100866015B1 (en) Hardmask composition having antireflective property and method of patterning materials using the same
KR100833212B1 (en) Hardmask composition having antireflective property
KR20150079199A (en) Hardmask composition, method of forming patterns using the hardmask composition and semiconductor integrated circuit device including the patterns
KR20100080139A (en) High etch resistant polymer having high carbon with aromatic rings, composition containing the same, and method of patterning materials using the same
KR20130078432A (en) Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition
KR101531610B1 (en) Composition for hardmask, method of forming patterns using the same, and semiconductor integrated circuit device including the patterns
KR101590809B1 (en) Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition
KR100826103B1 (en) Hardmask composition having antireflective property
WO2007139268A1 (en) Antireflective hardmask composition
KR20180054300A (en) Polymer, organic layer composition, organic layer, and method of forming patterns
KR101991698B1 (en) Compound, organic layer composition, and method of forming patterns

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E601 Decision to refuse application