WO2018079936A1 - 중합체, 유기막 조성물 및 패턴형성방법 - Google Patents

중합체, 유기막 조성물 및 패턴형성방법 Download PDF

Info

Publication number
WO2018079936A1
WO2018079936A1 PCT/KR2016/015409 KR2016015409W WO2018079936A1 WO 2018079936 A1 WO2018079936 A1 WO 2018079936A1 KR 2016015409 W KR2016015409 W KR 2016015409W WO 2018079936 A1 WO2018079936 A1 WO 2018079936A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
formula
layer
Prior art date
Application number
PCT/KR2016/015409
Other languages
English (en)
French (fr)
Korean (ko)
Inventor
김성환
박유신
임재범
김성현
정현일
Original Assignee
삼성에스디아이 주식회사
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 삼성에스디아이 주식회사 filed Critical 삼성에스디아이 주식회사
Publication of WO2018079936A1 publication Critical patent/WO2018079936A1/ko

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16Coating processes; Apparatus therefor
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26Processing photosensitive materials; Apparatus therefor
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26Processing photosensitive materials; Apparatus therefor
    • G03F7/34Imagewise removal by selective transfer, e.g. peeling away

Definitions

  • It relates to a novel polymer, an organic film composition comprising the polymer, and a pattern forming method using the organic film composition.
  • an organic layer called a hard mask layer which is a hard interlayer, may be formed.
  • the hard mask layer serves as an interlayer that transfers the fine pattern of the photoresist to the material layer through a selective etching process. Therefore, the hard mask layer needs to be etch resistant to withstand multiple etching processes. In addition, the hard mask layer requires a predetermined absorbance property to be usable as an antireflection film.
  • the hard mask layer is formed by a spin on coating method instead of the chemical vapor deposition method.
  • the spin silver coating method may use a hard mask composition having solubility, and the solubility of the hard mask composition also affects planarization characteristics required in a multi-patterning process.
  • One embodiment provides a novel polymer capable of forming an organic film having excellent etching resistance and securing planarization properties.
  • Another embodiment provides an organic film composition comprising the polymer.
  • Yet another embodiment provides a pattern forming method using an organic film composition comprising the polymer.
  • a polymer including a structural unit represented by the following Chemical Formula 1 is provided.
  • A is a 5 or 6-membered heteroaromatic ring containing two or more heteroatoms of the same or different kind
  • R 1 and R 2 are each independently an aromatic ring group, a heteroaromatic ring group, or a combination thereof,
  • R 3 is a divalent organic group
  • A includes two hetero atoms of the same kind or different kinds, and at least one of the two hetero atoms may be a nitrogen atom.
  • A is a six-membered hetero ring including two nitrogen atoms
  • A may be any one of the moieties listed in Group 1 below.
  • X 1 and X 2 are each nitrogen atom
  • X 3 is an oxygen atom, a sulfur atom or NR a ,
  • R a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, A substituted or unsubstituted C2 to C30 heterocyclic group, a hydroxy group, a halogen atom or a combination thereof,
  • R c is the same as the definition of mall R a .
  • R 1 and R 2 in Formula 1 may each independently be any one selected from the moieties listed in Groups 2 and 3 below.
  • Z 1 to Z 3 are each independently an oxygen atom, a sulfur atom or NR a , where R a is hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a hydroxy group, a halogen atom or a combination thereof.
  • R 3 may be represented by the following Formula 2.
  • Y 1 and Y 2 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to A C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a hydroxy group, a halogen atom or a combination thereof,
  • the polymer may have a weight average molecular weight of 500 to 20,000.
  • an organic film composition including the polymer and a solvent is provided.
  • the polymer may be included with respect to the total amount of the composition to the organic film coming from one weight 0/0 to 50% by weight.
  • a step of forming a material layer on a substrate applying an organic film composition comprising the above-described polymer and solvent on the material layer, heat treatment of the organic film composition to form a hard mask layer Forming a silicon-containing thin film layer on the hard mask layer, on the silicon-containing thin film layer
  • Forming a photoresist layer exposing and developing the photoresist layer to form a photoresist pattern, selectively removing the silicon-containing thin film layer and the hardmask layer using the photoresist pattern, and Exposing a portion, and etching the exposed portion of the material layer.
  • Applying the organic film composition may be performed by a spin-on coating method.
  • the method may further include forming a bottom anti-reflection layer (BARC) before forming the photoresist layer.
  • BARC bottom anti-reflection layer
  • the present invention provides a novel polymer capable of forming an organic film having excellent etching resistance and securing planarization and optical properties.
  • FIG. 1 is a flowchart illustrating a method of forming a pattern according to an embodiment
  • FIG. 2 is a reference diagram illustrating a method of evaluating planarization characteristics. [Best form for implementation of the invention]
  • 'substituted' means that a hydrogen atom in the 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, hydrazino, hydrazono, carbonyl, carbamyl, thiol, ester, carboxyl or salts thereof, sulfonic acid or salts thereof, phosphoric acid salts thereof, C1 to C20 alkyl groups, C2 to C20 alkenyl groups, C2 To C20 alkynyl group, C6 to C30 aryl group, C7 to C30 arylalkyl group, C1 to C30 alkoxy group, C1 to C20 heteroalkyl group, C2 to C20 heteroaryl group, C3 to C20 heteroarylalkyl group, C3 to C30 cycloalkyl group, C
  • Polymer according to one embodiment includes a structural unit represented by the following formula (1). [Formula 1]
  • A is a 5 or 6-membered heteroaromatic ring containing two or more heteroatoms of the same or different kind
  • R 1 and R 2 are each independently an aromatic ring group, a heteroaromatic ring group, or a combination thereof,
  • R 3 is a divalent organic group
  • the polymer comprises a heteroaromatic ring containing two or more heteroatoms of the same or different kind in its structural unit (denoted by A in Additive Formula 1).
  • the hetero atom may be, for example, N, 0, S, Te or Se, but is not limited thereto.
  • the number of hetero atoms included in A in Formula 1 may be, for example, one, two, three, or four, but is not limited thereto.
  • the polymer may secure an etching resistance basically by including an aromatic ring group.
  • an aromatic ring group by including two or more hetero atoms in the aromatic ring group, hydrogen bonding by the hetero atoms may be increased, thereby improving adhesion to the lower membrane.
  • heat resistance, solubility, and gap-fill characteristics can be improved.
  • A includes two heteroatoms of the same kind or different kinds, and at least one of the two hetero atoms may be a nitrogen atom.
  • A may be a six-membered hetero ring including two nitrogen atoms, or a five-membered hetero ring including one nitrogen atom and one of an oxygen atom and a sulfur atom.
  • a in Formula 1 may be any one of the moieties listed in Group 1 below, but is not limited thereto.
  • X 1 and X 2 are each nitrogen atom
  • X 3 is an oxygen atom, a sulfur atom or NR a ,
  • R a is hydrogen, substituted or unsubstituted C1 to C30 alkyl group, substituted or Unsubstituted C6 to C30 aryl group, substituted or unsubstituted C7 to C30 arylalkyl group, substituted or unsubstituted C1 to C30 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocyclic group, hydroxy group, halogen atom or these Is a combination of
  • R c is the same as the definition of R a .
  • the position at which each moiety is linked to Formula 1 in Group 1 is not particularly limited.
  • the polymer comprises a hetero ring represented by A in Formula 1, wherein the hetero ring is, for example, a structure blocked by another ring (where the blocked structure is a ring portion containing a hetero atom, for example, Open structure).
  • R 1 and R 2 may be any one selected from the moieties listed independently of Groups 2 and 3, respectively, but is not limited thereto.
  • Z 1 to Z 3 are each independently an oxygen atom, a sulfur atom or NR a , where R a is hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a hydroxy group, a halogen atom or a combination thereof.
  • the position at which each moiety is linked to Formula 1 in Groups 2 and 3 is not particularly limited.
  • R 3 representing a linking group in Formula 1 is not particularly limited as long as it is a divalent organic group.
  • at least one hydrogen in the moiety is A hydroxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or It may be a form substituted by a combination thereof, but is not limited thereto.
  • R 3 may be represented by the following Formula 2, but is not limited thereto.
  • ⁇ ⁇ and ⁇ 2 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 Heteroalkyl group, substituted or unsubstituted C2 to C30 heterocyclic group, hydroxy group, halogen atom or a combination thereof,
  • At least one of In Formula 2 ⁇ 1 and ⁇ 2 may be either one selected from the cyclic groups listed in the group 2, or any one selected from the heterocyclic groups listed in the group 3 is not limited thereto no.
  • the polymer described above may comprise at least one polycyclic ring group.
  • at least one of R 1 and R 2 may be a polycyclic ring group including two or more rings.
  • R 3 may be a polycyclic ring group including two or more rings.
  • the polymer may have a weight average molecular weight of about 500 to 20,000.
  • a weight average molecular weight in the above range it can be optimized by adjusting the carbon content and the solubility in the solvent of the organic film composition (eg hard mask composition) comprising the polymer.
  • the polymer When the polymer is used as an organic film material, it is possible not only to form a uniform thin film without formation of pin-holes and voids or deterioration of thickness distribution during the baking process, but also when a step exists in the lower substrate (black film) or When forming a pattern, excellent gap-fill and planarization properties can be provided.
  • an organic film comprising the above-described polymer and a solvent To provide a composition.
  • the solvent is not particularly limited as long as it has a sufficient solubility or dispersibility in the polymer, for example, propylene glycol, propylene glycol
  • the polymer may comprise from about 0.1 to 50 parts by weight 0/0 with respect to the total amount of the organic film composition. By including the polymer in the above range it was possible to control the thickness, surface roughness and degree of planarization of the organic film.
  • the organic film composition may further include additives such as a surfactant, a crosslinking agent, a thermal acid generator, and a plasticizer.
  • additives such as a surfactant, a crosslinking agent, a thermal acid generator, and a plasticizer.
  • Such surfactants include, for example, alkylbenzenesulfonic acid salts, alkylpyridinium salts,
  • Polyethylene glycol, crab quaternary ammonium salts and the like can be used, but are not limited thereto.
  • the crosslinking agent may be, for example, melamine type, substituted element type, or these polymer type.
  • the cross-linking agent having at least two crosslinking forming substituents, e.g., methoxy methylated glycosides ruril, butoxy methylated glycosides ruril, methoxy hydroxy melamine, buteuk when melamine, methoxy methylated benzoguanamine, buteuk when Compounds, such as methylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methimethylated thiourea, or butoxymethylated thiourea, can be used.
  • a crosslinking agent having high heat resistance may be used as the crosslinking agent.
  • numerator can be used.
  • the thermal acid generator is, for example, ⁇ - leulusulfonic acid, trifluoromethanesulfonic acid, pyridinium ⁇ _ leulusulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid,
  • Acidic compounds such as hydroxybenzoic acid, naphthalenecarboxylic acid, and / or 2,4,4,6-tetrabromocyclonuxadienone, benzointosylate, 2-nitrobenzyltosylate, and the like Eutectic acid alkyl esters may be used, but is not limited thereto.
  • the additive may be included in an amount of about 0.001 to 40 parts by weight based on 100 parts by weight of the organic film composition. By including in the said range, solubility can be improved without changing the optical characteristic of an organic film composition.
  • the organic film composition prepared using the above-described organic film composition prepared using the above-described organic film composition
  • the organic layer may be in the form of the above-described organic film composition, for example, coated on a substrate and cured by heat treatment, and may include, for example, an organic thin film used in an electronic device such as a hard mask layer, a planarization film, a regenerative film, a filler, and the like.
  • an organic thin film used in an electronic device such as a hard mask layer, a planarization film, a regenerative film, a filler, and the like.
  • FIG. 1 is a flowchart illustrating a pattern forming method according to an embodiment.
  • a method of forming a pattern includes forming a material layer on a substrate (S1), applying an organic film composition including the above-described polymerizer and a solvent on the material layer (S2), and applying the organic film composition to the organic film composition.
  • Exposing and developing to form a photoresist pattern S6), selectively removing the silicon-containing thin film layer and the hardmask layer using the photoresist pattern, and exposing a portion of the material layer (S7), and Etching (S8) 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, for example, a metal layer such as aluminum or copper, 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 organic film composition is as described above, it may be prepared in a solution form and applied by a spin-on coating method. At this time, the coating thickness of the organic film composition is not particularly limited, and for example, may be applied to a thickness of about 50 to 10,000 A.
  • the heat treatment of the organic film composition may be performed at, for example, about 100 to 500 ° C. It can be performed for 10 seconds to 1 hour.
  • the silicon-containing thin film layer may be formed of a material such as SiCN, SiOC, SiON, SiOCN, SiC, SiO, and / or SiN.
  • a bottom anti-reflective coating may be further formed on the silicon-containing thin film layer before the forming of the photoresist layer.
  • Exposing the photoresist layer may be performed using, for example, ArF, KrF, or EUV. It is also possible to perform a heat treatment process at about 100 to 500 ° C after exposure.
  • Etching the exposed portion of the material layer may be performed by dry etching using an etching gas, which may use, for example, CHF 3 , CF 4 , Cl 2 , BC1 3, and a combination thereof.
  • an etching gas which may use, for example, CHF 3 , CF 4 , Cl 2 , BC1 3, and a combination thereof.
  • the etched material layer may be formed in a plurality of patterns, and the plurality of patterns may be a metal pattern, a semiconductor pattern, an insulation pattern, or the like, and may be applied to, for example, various patterns in a semiconductor integrated circuit device.
  • the solution was prepared by adding 120 g of monomethylether acetate. Diethyl sulfate (0.31 g) was added to the solution, followed by stirring at 100 ° C for 10 hours.
  • the reaction mixture is cooled to room temperature, and the reaction mixture is slowly added to the stirring DIW (800 g). Filter the solids and wash them with DIW (300g) three times. After releasing the solid in ethanol (300g) and then filtered again to remove the residual solvent under reduced pressure to give the compound 3a.
  • the low molecular weight was removed to obtain a polymer including the structural unit represented by the following Chemical Formula 1-4.
  • a solution was prepared by adding Compound 5b (14.9 g, 0.05 mol), pyrenecarboxaldehyde (11.5 g, 0.05 mol) and 120 g of propylene glycol monomethyl ether acetate to the flask. Diethyl sulfate (0.39 g) was added to the solution, followed by stirring at 100 ° C for 10 hours. Upon completion of the polymerization, it is precipitated in methanol to give monomer and
  • the low molecular weight was removed to obtain a polymer including the structural unit represented by the following Chemical Formula 1-5.
  • Samples were taken from the polymerization reactions at 1 hour intervals, and the weight average molecular weight of the sample was measured to complete reaction when the weight average molecular weight was 1,800 to 2,500.
  • the reaction mixture was slowly cooled to room temperature, and then added to 40 g of the distilled water and 400 g of methanol, followed by strong stirring. The supernatant was removed, and the precipitate was dissolved in 80 g of propylene glycol monomethyl ether acetate (PGMEA), followed by vigorous stirring with 320 g of methanol, followed by standing (primary). The supernatant obtained at this time is removed again and the precipitate is propylene glycol.
  • PGMEA propylene glycol monomethyl ether acetate
  • the polymer obtained in Polymerization Example 1 was mixed with propylene glycol monomethyl ether acetate (PGMEA).
  • PGMEA propylene glycol monomethyl ether acetate
  • a polymer obtained in Polymerization Example 2 was used instead of the polymer obtained in Polymerization Example 1. Except that a hard mask composition was prepared in the same manner as in Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Polymerization Example 3 was used instead of the polymer obtained in Polymerization Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Polymerization Example 4 was used instead of the polymer obtained in Polymerization Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Polymerization Example 5 was used instead of the polymer obtained in Polymerization Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Comparative Polymerization Example 1 was used instead of the polymer obtained in Polymerization Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Comparative Polymerization Example 2 was used instead of the polymer obtained in Polymerization Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the polymer obtained in Comparative Polymerization Example 3 was used instead of the polymer obtained in Polymerization Example 1.
  • Evaluation 1 heat resistance evaluation
  • the hardmask composition (polymer content: 10.0 weight 0 /.) According to Examples 1 to 5 was spin coated onto a silicon wafer, followed by 5 minutes at 400 ° C.
  • the thickness of the thin film formed by ⁇ -MAC thin film thickness meter was re-established.
  • the thin film has a small thickness reduction rate during heat treatment at 400 degrees Celsius.
  • Example 1 to 5 and Comparative Examples hardmask composition according to 1 to 3 (10 parts by weight 0/0 increasing polymer content) on a silicon wafer. Subsequently, after the heat treatment at 400 ° C for 2 minutes to form a thin film, the thickness of the formed thin film was measured using a ST-5000 thin film thickness meter of K-MAC.
  • the etching rate (bulk etch rate
  • N 2/0 2 heunhap calculated the gas instead of CFx gas (10 ( ⁇ 7 600 ⁇ / 420 ⁇ 4/600 ⁇ / 150 using 2) removal rate by the following equation 1 similarly subjected to dry etching for 120 seconds.
  • etching rates for Examples 1 to 5 the hard mask thin film formed from the composition Comparative Examples 1 to 3 N 2/0 2 heunhap gas as compared with the thin film formed from a hardmask composition according to according to the It can be seen that low.
  • the thin film formed from the hard mask compositions according to Examples 1 to 5 has a lower etching rate for CFx gas than the thin film formed from the hard mask compositions according to Comparative Examples 1 to 2.
  • Examples 1 to 5 and Comparative Examples hardmask composition according to 1 to 3 (polymer content: 5 wt%) of the silicon wafer patterned (trench width ⁇ ⁇ ⁇ , trench depth lOOnm) spin-on coating, and The planarization characteristics of the thin film formed by heat treatment at 400 ° C. for 120 seconds were observed.
  • the planarization characteristics were quantified by the formula 2 shown in FIG. 2 by measuring the thickness of the hard mask layer from the image of the pattern cross section observed by SEM.
  • FIG. 2 denotes a value obtained by averaging the thickness of the thin film measured at any three points where no pattern is formed on the substrate, and h 2 is a thin film measured at any three point where the pattern is formed on the substrate.
  • the flattening characteristic is excellent as the difference between h and h 2 is not large, and the flattening characteristic is smaller as the planarization value is smaller. would be excellent.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Materials For Photolithography (AREA)
PCT/KR2016/015409 2016-10-27 2016-12-28 중합체, 유기막 조성물 및 패턴형성방법 WO2018079936A1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2016-0141244 2016-10-27
KR1020160141244A KR101994367B1 (ko) 2016-10-27 2016-10-27 중합체, 하드마스크 조성물 및 패턴형성방법

Publications (1)

Publication Number Publication Date
WO2018079936A1 true WO2018079936A1 (ko) 2018-05-03

Family

ID=62025093

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2016/015409 WO2018079936A1 (ko) 2016-10-27 2016-12-28 중합체, 유기막 조성물 및 패턴형성방법

Country Status (3)

Country Link
KR (1) KR101994367B1 (zh)
TW (1) TWI641913B (zh)
WO (1) WO2018079936A1 (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102171075B1 (ko) * 2018-07-12 2020-10-28 삼성에스디아이 주식회사 중합체, 하드마스크 조성물 및 패턴 형성 방법
KR102244470B1 (ko) 2018-07-18 2021-04-23 삼성에스디아이 주식회사 중합체, 유기막 조성물 및 패턴 형성 방법
KR102303554B1 (ko) 2018-12-26 2021-09-16 삼성에스디아이 주식회사 중합체, 하드마스크 조성물 및 패턴 형성 방법

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996020253A1 (en) * 1994-12-28 1996-07-04 Cambridge Display Technology Ltd. Polymers for use in optical devices
JP2006259249A (ja) * 2005-03-17 2006-09-28 Shin Etsu Chem Co Ltd フォトレジスト下層膜形成材料及びパターン形成方法
KR100819162B1 (ko) * 2007-04-24 2008-04-03 제일모직주식회사 반사방지성을 갖는 하드마스크 조성물 및 이를 이용한재료의 패턴화 방법
KR20140069163A (ko) * 2011-09-29 2014-06-09 닛산 가가쿠 고교 가부시키 가이샤 디아릴아민 노볼락 수지
KR20140144207A (ko) * 2012-03-27 2014-12-18 닛산 가가쿠 고교 가부시키 가이샤 페닐인돌 함유 노볼락 수지를 포함하는 레지스트 하층막 형성 조성물

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006036019A1 (de) * 2006-08-02 2008-02-07 Pemeas Gmbh Membran-Elektroden-Einheit und Brennstoffzellen mit erhöhter Leistung
KR101667788B1 (ko) * 2013-12-31 2016-10-19 제일모직 주식회사 하드마스크 조성물 및 이를 사용한 패턴 형성 방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996020253A1 (en) * 1994-12-28 1996-07-04 Cambridge Display Technology Ltd. Polymers for use in optical devices
JP2006259249A (ja) * 2005-03-17 2006-09-28 Shin Etsu Chem Co Ltd フォトレジスト下層膜形成材料及びパターン形成方法
KR100819162B1 (ko) * 2007-04-24 2008-04-03 제일모직주식회사 반사방지성을 갖는 하드마스크 조성물 및 이를 이용한재료의 패턴화 방법
KR20140069163A (ko) * 2011-09-29 2014-06-09 닛산 가가쿠 고교 가부시키 가이샤 디아릴아민 노볼락 수지
KR20140144207A (ko) * 2012-03-27 2014-12-18 닛산 가가쿠 고교 가부시키 가이샤 페닐인돌 함유 노볼락 수지를 포함하는 레지스트 하층막 형성 조성물

Also Published As

Publication number Publication date
KR20180046236A (ko) 2018-05-08
TWI641913B (zh) 2018-11-21
TW201816517A (zh) 2018-05-01
KR101994367B1 (ko) 2019-06-28

Similar Documents

Publication Publication Date Title
KR101829750B1 (ko) 중합체, 유기막 조성물, 및 패턴형성방법
US9158201B2 (en) Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition
KR20130078432A (ko) 하드마스크 조성물용 모노머, 상기 모노머를 포함하는 하드마스크 조성물 및 상기 하드마스크 조성물을 사용하는 패턴형성방법
TWI535697B (zh) 硬罩幕組成物與其使用的單體及其圖案形成方法
WO2018079936A1 (ko) 중합체, 유기막 조성물 및 패턴형성방법
WO2017126780A1 (ko) 유기막 조성물, 및 패턴형성방법
TWI644999B (zh) 聚合物、有機層組成物與形成圖案之方法
KR102296794B1 (ko) 유기막 조성물 및 패턴형성방법
KR101976016B1 (ko) 중합체, 유기막 조성물 및 패턴형성방법
KR102036681B1 (ko) 화합물, 유기막 조성물, 및 패턴형성방법
KR102246692B1 (ko) 화합물, 유기막 조성물, 유기막 및 패턴 형성 방법
KR102134268B1 (ko) 모노머, 중합체, 유기막 조성물 및 패턴 형성 방법
KR102134266B1 (ko) 모노머, 중합체, 유기막 조성물 및 패턴 형성 방법
KR101991698B1 (ko) 화합물, 유기막 조성물, 및 패턴형성방법
KR20180138405A (ko) 유기막 조성물, 중합체 및 패턴 형성 방법
JP7428766B2 (ja) ハードマスク組成物、ハードマスク層およびパターン形成方法
KR102284581B1 (ko) 화합물, 유기막 조성물 및 패턴 형성 방법
KR102151674B1 (ko) 중합체, 유기막 조성물 및 패턴 형성 방법
TWI679496B (zh) 硬罩幕組成物與形成圖案的方法
KR102129511B1 (ko) 화합물, 유기막 조성물, 및 패턴 형성 방법
KR101994366B1 (ko) 중합체, 유기막 조성물 및 패턴형성방법
KR102018237B1 (ko) 중합체, 유기막 조성물 및 패턴형성방법
US10332751B2 (en) Monomer, organic layer composition, organic layer, and method of forming patterns
WO2019088396A1 (ko) 중합체, 유기막 조성물 및 패턴 형성 방법

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16919686

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16919686

Country of ref document: EP

Kind code of ref document: A1