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WO2018199419A1 - Resist underlayer composition and method of forming patterns using the resist underlayer composition - Google Patents

Resist underlayer composition and method of forming patterns using the resist underlayer composition Download PDF

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Publication number
WO2018199419A1
WO2018199419A1 PCT/KR2017/013813 KR2017013813W WO2018199419A1 WO 2018199419 A1 WO2018199419 A1 WO 2018199419A1 KR 2017013813 W KR2017013813 W KR 2017013813W WO 2018199419 A1 WO2018199419 A1 WO 2018199419A1
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WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
resist underlayer
chemical formula
Prior art date
Application number
PCT/KR2017/013813
Other languages
French (fr)
Inventor
Yoojeong CHOI
Shinhyo BAE
Beomjun Joo
Soonhyung Kwon
Hyeon Park
Jaeyeol Baek
Kwen-Woo Han
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Samsung Sdi Co., Ltd.
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Application filed by Samsung Sdi Co., Ltd. filed Critical Samsung Sdi Co., Ltd.
Publication of WO2018199419A1 publication Critical patent/WO2018199419A1/en

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    • 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
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/094—Multilayer resist systems, e.g. planarising 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
    • G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
    • 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
    • G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
    • 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
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • 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
    • H01L21/0274—Photolithographic processes
    • 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
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/324—Thermal treatment for modifying the properties of semiconductor bodies, e.g. annealing, sintering

Definitions

  • the present invention relates to a resist underlayer composition and a method of forming a pattern using the same. More particularly, the present invention relates to a photoresist underlayer composition formed between a semiconductor substrate and a photoresist layer and a method of forming a photoresist pattern using the underlayer.
  • the lithographic technique includes coating a photoresist layer on a semiconductor substrate such as a silicon wafer, exposing and developing it to form a thin layer, irradiating activated radiation such as ultraviolet (UV) while disposing a mask pattern having a pattern of a device, developing the resultant to obtain a photoresist pattern, etching the substrate using the photoresist pattern as a protective layer to form a fine pattern corresponding to the pattern on the surface of the substrate.
  • activated radiation such as ultraviolet (UV)
  • an activated radiation having a short wavelength such as an i-line (365 nm), a KrF excimer laser (a wavelength of 248 nm), an ArF excimer laser (a wavelength of 193 nm), and the like is used for exposure of a photoresist. Accordingly, research on solving a problem of the activated radiation due to a diffused reflection from a semiconductor substrate, a standing wave, or the like has been made by interposing a resist underlayer having optimal reflectance between the photoresist and the semiconductor substrate.
  • a high energy ray such as EUV (extreme ultraviolet; a wavelength of 13.5 nm), an E-beam (electron beam), and the like as a light source for manufacturing the fine pattern in addition to the activated radiation has been used, and the light source has no reflection from the substrate, but research on improving adherence of the resist to the lower layer has been widely made to improve a collapse of the pattern. In addition, research on improving etch selectivity and chemical resistance of the resist underlayer in addition to decrease of the problems caused by the light source has been widely made.
  • the invention is directed to a resist underlayer composition having optimal reflectance in a particular wavelength and simultaneously, improved coating properties, planarization characteristics, adherence to a photoresist, and a fast etch rate.
  • the invention is also directed to a method of forming patterns using the resist underlayer composition.
  • a resist underlayer composition includes a polymer including a moiety represented by Chemical Formula 1 and a solvent.
  • a is an integer of 0 to 3
  • R 1 is hydrogen, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C1 to C30 heteroalkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkynyl group, or a combination thereof,
  • R 1 is a linking point (*)
  • R 0 is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
  • R 2 and R 3 are independently a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
  • b and c are independently an integer of 0 to 3
  • * is a linking point
  • R 2 and R 3 may independently include at least one ester (-COO-), ether (-CO-), or -CS- in the structure thereof or at least one substituted or unsubstituted C1 to C30 alkylene group, or a substituted or unsubstituted C1 to C30 heteroalkylene group in the structure thereof.
  • R 1 when a is 0, R 1 may be a C1 to C30 alkyl group, a C1 to C30 alkyl group substituted with at least one hydroxy group, a C1 to C30 heteroalkyl group, a C1 to C30 heteroalkyl group substituted with at least one hydroxy group, or a combination thereof, and in Chemical Formula 1, when a is 1, R 0 may include at least one ester (-COO-), ether (-CO-), or -CS- in the structure thereof or at least one substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C1 to C30 alkylene group including a substituted or unsubstituted C1 to C30 heteroalkylene group, a C1 to C30 alkylene group substituted with at least one hydroxy group, or a C1 to C30 heteroalkylene group.
  • a weight average molecular weight of the polymer may be 1,000 to 100,000.
  • the composition may further include a cross-linking agent having at least two cross-linking sites.
  • the composition may further include an additive of a surfactant, a thermal acid generator, a plasticizer, or a combination thereof.
  • a method of forming patterns includes forming an etching subject layer on a substrate, coating the resist underlayer composition on the etching subject layer to form a resist underlayer, forming a photoresist pattern on the resist underlayer, and sequentially etching the resist underlayer and the etching subject layer using the photoresist pattern as an etching mask.
  • the step of forming the photoresist pattern may include forming a photoresist layer on the resist underlayer, exposing the photoresist layer, and developing the photoresist layer.
  • the step of forming the resist underlayer may further include heat-treating the coated resist underlayer composition at a temperature of 100 °C to 500 °C.
  • the invention provides a resist underlayer composition having an optimized reflectance in a predetermined wavelength and simultaneously improved coating properties, planarization characteristics, and a fast etch rate.
  • the invention also provides a method of forming patterns using the resist underlayer composition.
  • FIGS. 1 to 5 are cross-sectional views for explaining a method of forming patterns using a resist underlayer composition according to an embodiment.
  • substrate 102 thin layer
  • resist underlayer 106 photoresist layer
  • Example embodiments of the present disclosure will hereinafter be described in detail, and may be easily performed by a person skilled in the art. However, this disclosure may be embodied in many different forms and is not construed as limited to the example embodiments set forth herein.
  • 'substituted' refers to replacement of a hydrogen atom of a compound by a substituent selected from a halogen atom (F, Br, Cl, or I), a hydroxy group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a vinyl 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
  • hetero' refers to inclusion of 1 to 10 heteroatoms selected from N, O, S, and P.
  • '*' refers to a linking point of a compound or a compound moiety.
  • a resist underlayer composition according to an embodiment includes a polymer including a moiety represented by Chemical Formula 1 and a solvent.
  • a is an integer of 0 to 3
  • R 1 is hydrogen, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C1 to C30 heteroalkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkynyl group, or a combination thereof,
  • R 1 is a linking point (*)
  • R 0 is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
  • R 2 and R 3 are independently a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
  • b and c are independently an integer of 0 to 3
  • * is a linking point
  • the moiety represented by Chemical Formula 1 has a structure of a triazine backbone in the core and three oxygen atoms linked with the triazine.
  • the moiety has this structure and thus a relatively high refractive index (n) and low extinction coefficient (k) with respect an ArF excimer laser (a wavelength of 193 nm).
  • n refractive index
  • k low extinction coefficient
  • an ArF excimer laser a wavelength of 193 nm. Accordingly, when a composition including the polymer is, for example, used as a photoresist underlayer material, the photoresist underlayer material may have optimal reflectance from an etched layer to a light source and thus suppresses a light interference effect and in addition, has high etch selectivity with a photoresist layer during the etching process and improved flatness.
  • the moiety represented by Chemical Formula 1 may contain at least one hydroxy group and thus further secures coating uniformity due to this structure.
  • R 1 may be a C1 to C30 alkyl group, a C1 to C30 alkyl group substituted with at least one hydroxy group, a C1 to C30 heteroalkyl group, a C1 to C30 heteroalkyl group substituted with at least one hydroxy group, or a combination thereof, but is not limited thereto.
  • R 0 may be a substituted or unsubstituted C1 to C30 alkylene group, a C1 to C30 alkylene group substituted with at least one hydroxy group, a C1 to C30 heteroalkylene group, a C1 to C30 heteroalkylene group substituted with at least one hydroxy group, or a combination thereof, but is not limited thereto.
  • R 1 when a is 0, R 1 may be a linear or branched C1 to C30 alkyl group wherein at least one hydrogen is replaced by a hydroxy group.
  • R 1 may be a linear or branched C1 to C30 heteroalkyl group wherein at least one hydrogen is replaced by a hydroxy group.
  • a heteroatom in the heteroalkyl group may be present at any position of the heteroalkyl group.
  • R 2 and R 3 may independently include at least one of ester (-COO-), ether (-CO-), and -CS- in the structure thereof or may independently include at least one substituted or unsubstituted C1 to C30 alkylene group, or a substituted or unsubstituted C1 to C30 heteroalkylene group in the structure thereof.
  • the polymer is stable in an organic solvent and is stable under heat, when a resist underlayer composition including the polymer is, for example, used as a photoresist underlayer material, a resist underlayer formed thereof may be minimized from delamination caused by the solvent or the heat during a process of forming a photoresist pattern or may minimize generation of a byproduct such as a chemical material and the like and a thickness loss caused by a photoresist solvent thereon.
  • the compound has improved solubility and thus may form a resist underlayer having improved coating uniformity.
  • the polymer may be a copolymer including at least one second moiety derived from a different monomolecule in addition to the moiety.
  • the polymer may have a weight average molecular weight of 1,000 to 100,000. Specifically, the polymer may have a weight average molecular weight of 1,000 to 50,000, and more specifically 1,000 to 20,000. When the polymer has a weight average molecular weight within the ranges, the amount of carbon and solubility in a solvent of the resist underlayer composition including the polymer may be optimized.
  • a uniform thin layer may not only be obtained without forming a pin-hole or a void which deteriorates a thickness distribution during a baking process, but improved gap-fill and planarization characteristics may also be obtained when a lower substrate (or a layer) has a step or is patterned.
  • the solvent may be any solvent having sufficient dissolubility or dispersibility for the polymer and may include, for example, at least one selected from propylene glycol, propylene glycol diacetate, methoxy propanediol, diethylene glycol, diethylene glycol butylether, tri(ethylene glycol)monomethylether, propylene glycol monomethylether, propylene glycol monomethylether acetate, cyclohexanone, ethyllactate, gamma-butyrolactone, N,N-dimethyl formamide, N,N-dimethyl acetamide, methyl pyrrolidone, methyl pyrrolidinone, acetylacetone, and ethyl 3-ethoxypropionate.
  • the polymer may be included in an amount of 0.1 to 50 wt%, 0.1 to 30 wt%, or 0.1 to 15 wt% based on a total amount of the resist underlayer composition.
  • a thickness, a surface roughness, and a planarization of the formed thin layer may be controlled.
  • the resist underlayer composition may further include a cross-linking agent.
  • the cross-linking agent may be, for example, a melamine-based, substituted urea-based, or a polymer-based cross-linking agent.
  • the cross-linking agent may be a cross-linking agent having at least two cross-linking forming substituents, for example, a compound such as methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, methoxymethylatedurea, butoxymethylatedurea, methoxymethylated thiourea, or butoxymethylated thiourea, and the like.
  • the cross-linking agent may be a cross-linking agent having high heat resistance and may be, for example, a compound including a cross-linking substituent including an aromatic ring (for example, a benzene ring or a naphthalene ring) in the molecule.
  • the cross-linking agent may have, for example, two or more cross-linking sites.
  • the resist underlayer composition may further include at least one other polymer of an acryl-based resin, an epoxy-based resin, a novolac resin, a glycoluril-based resin, and a melamine-based resin in addition to the compound including a structural unit represented by Chemical Formula 1, but is not limited thereto.
  • the resist underlayer composition may further include an additive of a surfactant, a thermal acid generator, a plasticizer, or a combination thereof.
  • the surfactant may include, for example, an alkylbenzenesulfonate salt, an alkyl pyridinium salt, a polyethylene glycol, a quaternary ammonium salt, a fluoro alkyl-based compound, and the like, but is not limited thereto.
  • the thermal acid generator may be, for example, an acidic compound such as p-toluene sulfonic acid, trifluoromethane sulfonic acid, pyridinium p-toluene sulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthalene carbonic acid, and the like and/or 2,4,4,6-tetrabromocyclohexadienone, benzointosylate, 2-nitrobenzyltosylate, other organosulfonic acid alkylester, and the like, but is not limited thereto.
  • an acidic compound such as p-toluene sulfonic acid, trifluoromethane sulfonic acid, pyridinium p-toluene sulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid
  • the additive may be present in an amount of 0.001 to 40 parts by weight based on 100 parts by weight of the resist underlayer composition. Within the ranges, solubility may be improved while optical properties of the resist underlayer composition are not changed.
  • a resist underlayer manufactured using the resist underlayer composition is provided.
  • the resist underlayer may be cured by heat treatment after coating the resist underlayer composition on, for example, a substrate, and may include, for example, an organic thin layer such as a planarization layer, an anti-reflection coating, a sacrificial layer, a filler, and the like that are used in an electronic device.
  • FIGs. 1 to 5 a method of forming patterns using the resist underlayer composition is described referring to FIGs. 1 to 5.
  • FIGs. 1 to 5 are cross-sectional views explaining a method of forming patterns using a resist underlayer composition according to an embodiment.
  • the etching subject may be a thin layer 102 formed on a substrate 100 (for example, a semiconductor substrate).
  • the etching subject is limited to the thin layer 102.
  • An entire surface of the thin layer 102 is washed to remove impurities and the like remaining thereon.
  • the thin layer 102 may be, for example, a silicon nitride layer, a polysilicon layer, or a silicon oxide layer.
  • the resist underlayer composition including the polymer having the structural unit represented by Chemical Formula 1 and a solvent is spin-coated on the surface of the washed thin layer 102.
  • the coated composition is dried and baked to form a resist underlayer 104 on the thin layer 102.
  • the baking may be performed at 100 °C to 500 °C.
  • the baking may be performed at 100 °C to 300 °C.
  • the resist underlayer composition is described above in detail and thus the detailed descriptions thereof will be omitted.
  • a photoresist layer 106 is formed by coating a photoresist on the resist underlayer 104.
  • the photoresist may be a positive-type photoresist containing a naphthoquinonediazide compound and a novolac resin, a chemically-amplified positive photoresist containing an acid generator capable of dissociating acid through exposure, a compound decomposed under presence of the acid and having increased dissolubility in an alkali aqueous solution, and an alkali soluble resin, a chemically-amplified positive-type photoresist containing an alkali-soluble resin capable of applying a resin increasing dissolubility in an alkali aqueous solution, and the like.
  • the substrate 100 having the photoresist layer 106 thereon is primarily baked.
  • the primary baking may be performed at about 90 °C to about 120 °C.
  • the photoresist layer 106 may be selectively exposed.
  • Exposure of the photoresist layer 106 may be, for example, performed by positioning an exposure mask having a predetermined pattern on a mask stage of an exposure apparatus and aligning the exposure mask 110 on the photoresist layer 106. Subsequently, light is radiated into the exposure mask 110 and a predetermined region of the photoresist layer 106 formed on the substrate 100 selectively reacts with light passing the exposure mask 110.
  • Examples of the light used during the exposure may be an ArF laser (a laser of ArF) having a wavelength of 193 nm and 248 nm, EUV (extreme ultraviolet) having a wavelength of 13.5 nm, and the like.
  • An exposed region 106b of the photoresist layer 106 may be relatively hydrophilic compared with a non-exposed region 106a of the photoresist layer 106. Accordingly, the exposed region 106b and non-exposed region 106a of the photoresist layer 106 may have different solubility from each other.
  • the substrate 100 is secondarily baked.
  • the secondary baking may be performed at about 90 °C to about 150 °C.
  • the exposed region 106b of the photoresist layer 106 becomes easily dissoluble with respect to a predetermined solvent due to the secondary baking.
  • the exposed region 106b of the photoresist layer 106 is dissolved and removed by a developing solution to form a photoresist pattern 108.
  • a developing solution such as tetra-methyl ammonium hydroxide (TMAH) and the like to finish the photoresist pattern 108.
  • TMAH tetra-methyl ammonium hydroxide
  • the photoresist pattern 108 is used as an etching mask to etch the resist underlayer 104. Through the etching, an organic layer pattern 112 is formed.
  • the etching may be, for example, dry etching using etching gas, and the etching gas may be, for example, CHF 3 , CF 4 , Cl 2 , BCl 3 , and a mixed gas thereof.
  • the photoresist pattern 108 is applied as an etching mask to etch the exposed thin layer 102. As a result, the thin layer is formed into a thin layer pattern 114.
  • Mw molecular weight
  • a reaction was performed for 2 hours or so at the same temperature and then, for 1 hour by increasing the reaction temperature up to 15 °C and for 5 hours by increasing the temperature up to room temperature (23 °C to 25 °C).
  • An additional amount of (3.7 g, 60 mmol) of ethanediol was added thereto.
  • an organic layer was separated from an aqueous layer and then, dried, and a solvent therein was removed.
  • a viscous material remaining there was dried at 35 °C for 2 days and was washed with water and methanol.
  • a reaction was performed at the same temperature for about 2 hours and then, for 1 hour by increasing the reaction temperature up to 15 °C and for 5 hours by increasing the temperature up to room temperature (23 °C to 25 °C). 5.4 g (60 mmol) of butanediol was added thereto. The obtained mixture was further stirred for 2 hours and an organic layer was separated from an aqueous layer and dried, and a solvent was removed therefrom. A viscous material remaining there was washed with water and methanol at 35 °C for 2 days.
  • An amount of the mixed solvent was controlled, so that the polymer was included in a solid content of 2 wt% based on a total weight of the resist underlayer composition.
  • Each resist underlayer composition was prepared according to the same method as Example 1 except for using each polymer according to Synthesis Examples 2 to 7.
  • a resist underlayer composition was prepared according to the same method as Example 1 except for using the polymer according to Comparative Synthesis Example 1.
  • compositions according to Examples 1 to 7 and Comparative Example 1 were respectively taken by 2 ml, applied on a 4 inch wafer, and spin-coated at 1,500 rpm for 20 seconds by using a spin coater (Mikasa Co., Ltd.). Subsequently, the coated compositions were cured at 230 °C for 90 seconds to respectively form 30 nm-thick thin layers. A refractive index (n) and an extinction coefficient (k) of each thin layer were measured under a condition of 800 A by using VASE Elliposmeters (J.A. Woollam Co.).
  • Example 1 1.94 0.29
  • Example 2 1.92 0.28
  • Example 3 1.99 0.29
  • Example 4 1.95 0.31
  • Example 5 1.97 0.29
  • Example 6 1.91 0.31
  • Example 7 1.88 0.26 Comparative Example 1 1.96 0.39
  • the refractive indices and extinction coefficients of the resist underlayer compositions according to Examples 1 to 7 were applicable as a resist underlayer at an ArF wavelength (193 nm and 248 nm), and thus a resist underlayer composition of the present invention turned out to have improved reflectance.
  • composition according to Examples 1, 4, 6, and 7 and Comparative Example 1 was taken by 2 ml and respectively applied on an 8-inch wafer and then, spin-coated at a main speed of 1,500 rpm for 20 seconds by using an auto track (ACT-8, TEL) and cured at 230 °C for 90 seconds to respectively form 300 nm-thick thin layers. Thicknesses of the thin layers horizontally at 51 points were measured to compare uniformity.
  • the resist underlayer compositions according to Examples 1, 4, and 6 showed improved coating uniformity compared with the resist underlayer composition according to Comparative Example 1.

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Abstract

Disclosed are a resist underlayer composition and a method of forming a pattern using the same. The resist underlayer composition includes a polymer having a moiety represented by Chemical Formula 1 and a solvent.

Description

RESIST UNDERLAYER COMPOSITION AND METHOD OF FORMING PATTERNS USING THE RESIST UNDERLAYER COMPOSITION
The present invention relates to a resist underlayer composition and a method of forming a pattern using the same. More particularly, the present invention relates to a photoresist underlayer composition formed between a semiconductor substrate and a photoresist layer and a method of forming a photoresist pattern using the underlayer.
Recently, the semiconductor industry has developed to an ultra-fine technique having a pattern of several to several tens nanometer size. Such ultrafine technique essentially needs effective lithographic techniques.
The lithographic technique includes coating a photoresist layer on a semiconductor substrate such as a silicon wafer, exposing and developing it to form a thin layer, irradiating activated radiation such as ultraviolet (UV) while disposing a mask pattern having a pattern of a device, developing the resultant to obtain a photoresist pattern, etching the substrate using the photoresist pattern as a protective layer to form a fine pattern corresponding to the pattern on the surface of the substrate.
As technology of manufacturing an ultra fine pattern is required, an activated radiation having a short wavelength such as an i-line (365 nm), a KrF excimer laser (a wavelength of 248 nm), an ArF excimer laser (a wavelength of 193 nm), and the like is used for exposure of a photoresist. Accordingly, research on solving a problem of the activated radiation due to a diffused reflection from a semiconductor substrate, a standing wave, or the like has been made by interposing a resist underlayer having optimal reflectance between the photoresist and the semiconductor substrate.
On the other hand, a high energy ray such as EUV (extreme ultraviolet; a wavelength of 13.5 nm), an E-beam (electron beam), and the like as a light source for manufacturing the fine pattern in addition to the activated radiation has been used, and the light source has no reflection from the substrate, but research on improving adherence of the resist to the lower layer has been widely made to improve a collapse of the pattern. In addition, research on improving etch selectivity and chemical resistance of the resist underlayer in addition to decrease of the problems caused by the light source has been widely made.
In addition, an attempt to improve adherence of the resist underlayer to the resist as well as the etch selectivity and the chemical resistance in addition to the decrease of the problems caused by a light source has been made.
The invention is directed to a resist underlayer composition having optimal reflectance in a particular wavelength and simultaneously, improved coating properties, planarization characteristics, adherence to a photoresist, and a fast etch rate.
The invention is also directed to a method of forming patterns using the resist underlayer composition.
According to an embodiment, a resist underlayer composition includes a polymer including a moiety represented by Chemical Formula 1 and a solvent.
[Chemical Formula 1]
Figure PCTKR2017013813-appb-I000001
In Chemical Formula 1,
a is an integer of 0 to 3,
when a is 0, R1 is hydrogen, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C1 to C30 heteroalkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkynyl group, or a combination thereof,
when a is an integer of 1 to 3, R1 is a linking point (*), R0 is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
R2 and R3 are independently a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
b and c are independently an integer of 0 to 3, and
* is a linking point.
According to an embodiment, in Chemical Formula 1, R2 and R3 may independently include at least one ester (-COO-), ether (-CO-), or -CS- in the structure thereof or at least one substituted or unsubstituted C1 to C30 alkylene group, or a substituted or unsubstituted C1 to C30 heteroalkylene group in the structure thereof.
According to an embodiment, in Chemical Formula 1, when a is 0, R1 may be a C1 to C30 alkyl group, a C1 to C30 alkyl group substituted with at least one hydroxy group, a C1 to C30 heteroalkyl group, a C1 to C30 heteroalkyl group substituted with at least one hydroxy group, or a combination thereof, and in Chemical Formula 1, when a is 1, R0 may include at least one ester (-COO-), ether (-CO-), or -CS- in the structure thereof or at least one substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C1 to C30 alkylene group including a substituted or unsubstituted C1 to C30 heteroalkylene group, a C1 to C30 alkylene group substituted with at least one hydroxy group, or a C1 to C30 heteroalkylene group.
According to an embodiment, a weight average molecular weight of the polymer may be 1,000 to 100,000.
According to an embodiment, the composition may further include a cross-linking agent having at least two cross-linking sites.
According to an embodiment, the composition may further include an additive of a surfactant, a thermal acid generator, a plasticizer, or a combination thereof.
According to another embodiment, a method of forming patterns includes forming an etching subject layer on a substrate, coating the resist underlayer composition on the etching subject layer to form a resist underlayer, forming a photoresist pattern on the resist underlayer, and sequentially etching the resist underlayer and the etching subject layer using the photoresist pattern as an etching mask.
According to an embodiment, the step of forming the photoresist pattern may include forming a photoresist layer on the resist underlayer, exposing the photoresist layer, and developing the photoresist layer.
According to an embodiment, the step of forming the resist underlayer may further include heat-treating the coated resist underlayer composition at a temperature of 100 °C to 500 °C.
Based on the above, the invention provides a resist underlayer composition having an optimized reflectance in a predetermined wavelength and simultaneously improved coating properties, planarization characteristics, and a fast etch rate. The invention also provides a method of forming patterns using the resist underlayer composition.
FIGS. 1 to 5 are cross-sectional views for explaining a method of forming patterns using a resist underlayer composition according to an embodiment.
Description of Symbols
100: substrate 102: thin layer
104: resist underlayer 106: photoresist layer
108: photoresist pattern 110: mask
112: organic layer pattern 114: thin layer pattern
Example embodiments of the present disclosure will hereinafter be described in detail, and may be easily performed by a person skilled in the art. However, this disclosure may be embodied in many different forms and is not construed as limited to the example embodiments set forth herein.
In the drawings, the thickness of layers, films, panels, regions, etc., are exaggerated for clarity and like reference numerals designate like elements throughout the specification. It will be understood that when an element such as a layer, film, region, or substrate is referred to as being "on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
As used herein, when a definition is not otherwise provided, 'substituted' refers to replacement of a hydrogen atom of a compound by a substituent selected from a halogen atom (F, Br, Cl, or I), a hydroxy group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a vinyl 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 C6 to C30 allyl group, a C1 to C30 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 C3 to C30 heterocycloalkyl group, and a combination thereof.
As used herein, when a definition is not otherwise provided, 'hetero' refers to inclusion of 1 to 10 heteroatoms selected from N, O, S, and P.
As used herein, when a definition is not otherwise provided, '*' refers to a linking point of a compound or a compound moiety.
Hereinafter, a resist underlayer composition according to an embodiment is described.
A resist underlayer composition according to an embodiment includes a polymer including a moiety represented by Chemical Formula 1 and a solvent.
[Chemical Formula 1]
Figure PCTKR2017013813-appb-I000002
In Chemical Formula 1,
a is an integer of 0 to 3,
when a is 0, R1 is hydrogen, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C1 to C30 heteroalkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkynyl group, or a combination thereof,
when a is an integer of 1 to 3, R1 is a linking point (*), R0 is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
R2 and R3 are independently a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
b and c are independently an integer of 0 to 3, and
* is a linking point.
The moiety represented by Chemical Formula 1 has a structure of a triazine backbone in the core and three oxygen atoms linked with the triazine. The moiety has this structure and thus a relatively high refractive index (n) and low extinction coefficient (k) with respect an ArF excimer laser (a wavelength of 193 nm). Accordingly, when a composition including the polymer is, for example, used as a photoresist underlayer material, the photoresist underlayer material may have optimal reflectance from an etched layer to a light source and thus suppresses a light interference effect and in addition, has high etch selectivity with a photoresist layer during the etching process and improved flatness.
The moiety represented by Chemical Formula 1 may contain at least one hydroxy group and thus further secures coating uniformity due to this structure.
For example, in Chemical Formula 1, when a is 0, R1 may be a C1 to C30 alkyl group, a C1 to C30 alkyl group substituted with at least one hydroxy group, a C1 to C30 heteroalkyl group, a C1 to C30 heteroalkyl group substituted with at least one hydroxy group, or a combination thereof, but is not limited thereto. In addition, for example, in Chemical Formula 1, when a is 1, R0 may be a substituted or unsubstituted C1 to C30 alkylene group, a C1 to C30 alkylene group substituted with at least one hydroxy group, a C1 to C30 heteroalkylene group, a C1 to C30 heteroalkylene group substituted with at least one hydroxy group, or a combination thereof, but is not limited thereto.
For example, in Chemical Formula 1, when a is 0, R1 may be a linear or branched C1 to C30 alkyl group wherein at least one hydrogen is replaced by a hydroxy group. For example, R1 may be a linear or branched C1 to C30 heteroalkyl group wherein at least one hydrogen is replaced by a hydroxy group. Herein, a heteroatom in the heteroalkyl group may be present at any position of the heteroalkyl group.
In addition, in Chemical Formula 1, R2 and R3 may independently include at least one of ester (-COO-), ether (-CO-), and -CS- in the structure thereof or may independently include at least one substituted or unsubstituted C1 to C30 alkylene group, or a substituted or unsubstituted C1 to C30 heteroalkylene group in the structure thereof.
Since the polymer is stable in an organic solvent and is stable under heat, when a resist underlayer composition including the polymer is, for example, used as a photoresist underlayer material, a resist underlayer formed thereof may be minimized from delamination caused by the solvent or the heat during a process of forming a photoresist pattern or may minimize generation of a byproduct such as a chemical material and the like and a thickness loss caused by a photoresist solvent thereon. In addition, the compound has improved solubility and thus may form a resist underlayer having improved coating uniformity.
Furthermore, the polymer may be a copolymer including at least one second moiety derived from a different monomolecule in addition to the moiety.
The polymer may have a weight average molecular weight of 1,000 to 100,000. Specifically, the polymer may have a weight average molecular weight of 1,000 to 50,000, and more specifically 1,000 to 20,000. When the polymer has a weight average molecular weight within the ranges, the amount of carbon and solubility in a solvent of the resist underlayer composition including the polymer may be optimized.
When the polymer is used as a material for a resist underlayer, a uniform thin layer may not only be obtained without forming a pin-hole or a void which deteriorates a thickness distribution during a baking process, but improved gap-fill and planarization characteristics may also be obtained when a lower substrate (or a layer) has a step or is patterned.
The solvent may be any solvent having sufficient dissolubility or dispersibility for the polymer and may include, for example, at least one selected from propylene glycol, propylene glycol diacetate, methoxy propanediol, diethylene glycol, diethylene glycol butylether, tri(ethylene glycol)monomethylether, propylene glycol monomethylether, propylene glycol monomethylether acetate, cyclohexanone, ethyllactate, gamma-butyrolactone, N,N-dimethyl formamide, N,N-dimethyl acetamide, methyl pyrrolidone, methyl pyrrolidinone, acetylacetone, and ethyl 3-ethoxypropionate.
The polymer may be included in an amount of 0.1 to 50 wt%, 0.1 to 30 wt%, or 0.1 to 15 wt% based on a total amount of the resist underlayer composition. When the polymer is included within the ranges, a thickness, a surface roughness, and a planarization of the formed thin layer may be controlled.
The resist underlayer composition may further include a cross-linking agent.
The cross-linking agent may be, for example, a melamine-based, substituted urea-based, or a polymer-based cross-linking agent. Preferably, the cross-linking agent may be a cross-linking agent having at least two cross-linking forming substituents, for example, a compound such as methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, methoxymethylatedurea, butoxymethylatedurea, methoxymethylated thiourea, or butoxymethylated thiourea, and the like.
The cross-linking agent may be a cross-linking agent having high heat resistance and may be, for example, a compound including a cross-linking substituent including an aromatic ring (for example, a benzene ring or a naphthalene ring) in the molecule. The cross-linking agent may have, for example, two or more cross-linking sites.
In addition, the resist underlayer composition may further include at least one other polymer of an acryl-based resin, an epoxy-based resin, a novolac resin, a glycoluril-based resin, and a melamine-based resin in addition to the compound including a structural unit represented by Chemical Formula 1, but is not limited thereto.
The resist underlayer composition may further include an additive of a surfactant, a thermal acid generator, a plasticizer, or a combination thereof.
The surfactant may include, for example, an alkylbenzenesulfonate salt, an alkyl pyridinium salt, a polyethylene glycol, a quaternary ammonium salt, a fluoro alkyl-based compound, and the like, but is not limited thereto.
The thermal acid generator may be, for example, an acidic compound such as p-toluene sulfonic acid, trifluoromethane sulfonic acid, pyridinium p-toluene sulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthalene carbonic acid, and the like and/or 2,4,4,6-tetrabromocyclohexadienone, benzointosylate, 2-nitrobenzyltosylate, other organosulfonic acid alkylester, and the like, but is not limited thereto.
The additive may be present in an amount of 0.001 to 40 parts by weight based on 100 parts by weight of the resist underlayer composition. Within the ranges, solubility may be improved while optical properties of the resist underlayer composition are not changed.
According to another embodiment, a resist underlayer manufactured using the resist underlayer composition is provided. The resist underlayer may be cured by heat treatment after coating the resist underlayer composition on, for example, a substrate, and may include, for example, an organic thin layer such as a planarization layer, an anti-reflection coating, a sacrificial layer, a filler, and the like that are used in an electronic device.
Hereinafter, a method of forming patterns using the resist underlayer composition is described referring to FIGs. 1 to 5.
FIGs. 1 to 5 are cross-sectional views explaining a method of forming patterns using a resist underlayer composition according to an embodiment.
Referring to FIG. 1, a subject for etching is prepared. The etching subject may be a thin layer 102 formed on a substrate 100 (for example, a semiconductor substrate). Hereinafter, the etching subject is limited to the thin layer 102. An entire surface of the thin layer 102 is washed to remove impurities and the like remaining thereon. The thin layer 102 may be, for example, a silicon nitride layer, a polysilicon layer, or a silicon oxide layer.
Subsequently, the resist underlayer composition including the polymer having the structural unit represented by Chemical Formula 1 and a solvent is spin-coated on the surface of the washed thin layer 102.
Then, the coated composition is dried and baked to form a resist underlayer 104 on the thin layer 102. The baking may be performed at 100 °C to 500 °C. For example, the baking may be performed at 100 °C to 300 °C. Specifically, the resist underlayer composition is described above in detail and thus the detailed descriptions thereof will be omitted.
Referring to FIG. 2, a photoresist layer 106 is formed by coating a photoresist on the resist underlayer 104.
Examples of the photoresist may be a positive-type photoresist containing a naphthoquinonediazide compound and a novolac resin, a chemically-amplified positive photoresist containing an acid generator capable of dissociating acid through exposure, a compound decomposed under presence of the acid and having increased dissolubility in an alkali aqueous solution, and an alkali soluble resin, a chemically-amplified positive-type photoresist containing an alkali-soluble resin capable of applying a resin increasing dissolubility in an alkali aqueous solution, and the like.
Subsequently, the substrate 100 having the photoresist layer 106 thereon is primarily baked. The primary baking may be performed at about 90 °C to about 120 °C.
Referring to FIG. 3, the photoresist layer 106 may be selectively exposed.
Exposure of the photoresist layer 106 may be, for example, performed by positioning an exposure mask having a predetermined pattern on a mask stage of an exposure apparatus and aligning the exposure mask 110 on the photoresist layer 106. Subsequently, light is radiated into the exposure mask 110 and a predetermined region of the photoresist layer 106 formed on the substrate 100 selectively reacts with light passing the exposure mask 110. Examples of the light used during the exposure may be an ArF laser (a laser of ArF) having a wavelength of 193 nm and 248 nm, EUV (extreme ultraviolet) having a wavelength of 13.5 nm, and the like.
An exposed region 106b of the photoresist layer 106 may be relatively hydrophilic compared with a non-exposed region 106a of the photoresist layer 106. Accordingly, the exposed region 106b and non-exposed region 106a of the photoresist layer 106 may have different solubility from each other.
Subsequently, the substrate 100 is secondarily baked. The secondary baking may be performed at about 90 °C to about 150 °C. The exposed region 106b of the photoresist layer 106 becomes easily dissoluble with respect to a predetermined solvent due to the secondary baking.
Referring to FIG. 4, the exposed region 106b of the photoresist layer 106 is dissolved and removed by a developing solution to form a photoresist pattern 108. Specifically, the exposed region 106b of the photoresist layer 106 is dissolved and removed by using a developing solution such as tetra-methyl ammonium hydroxide (TMAH) and the like to finish the photoresist pattern 108.
Subsequently, the photoresist pattern 108 is used as an etching mask to etch the resist underlayer 104. Through the etching, an organic layer pattern 112 is formed.
The etching may be, for example, dry etching using etching gas, and the etching gas may be, for example, CHF3, CF4, Cl2, BCl3, and a mixed gas thereof. Referring to FIG. 5, the photoresist pattern 108 is applied as an etching mask to etch the exposed thin layer 102. As a result, the thin layer is formed into a thin layer pattern 114.
Hereinafter, the present invention is described in more detail through Examples regarding synthesis of the polymer and preparation of a resist underlayer composition including the same. However, the present invention is technically not restricted by the following example embodiments.
Synthesis Examples
Synthesis Example 1
16.46 g (0.05 mol) of 2,2'-((6-(oxiran-2-ylmethoxy)-1,3,5-triazine-2,4-diyl)bis(oxy))diacetic acid, 3.1 g (0.05 mol) of ethylene glycol, 0.1.33 g (7 mmol) of p-toluene sulfonic acid, and 13 g of anisole were put in a 100 mL round flask equipped with a condenser and then, stirred with a magnetic bar while heated up to 150 °C to perform a polymerization reaction. After performing the reaction for 20 hours, the polymerization reaction solution was cooled down to room temperature (23 °C to 25 °C) and diluted by using 30 g of HBM (methyl 2-hydroxyisobutyrate) and then, added to 500 g of isopropylalcohol (IPA). After stirring the mixture and allowing it to stand, a supernatant was removed therefrom. Subsequently, a purification process of diluting the purified resin layer with HBM (methyl 2-hydroxyisobutyrate) again, adding 500 g of IPA thereto, stirring the obtained mixture, and allowing it to stand was repeated four times to remove low molecules and catalysts. Finally, a polymer including a structural unit represented by Chemical Formula 1-1 (a molecular weight (Mw) = 5,700) was obtained.
[Chemical Formula 1-1]
Figure PCTKR2017013813-appb-I000003
Synthesis Example 2
15.7 g (0.06 mol) of 2,2',2''-((1,3,5-triazine-2,4,6-triyl)tris(oxy))triethanol, 5.9 g (0.05 mol) of succinic acid, 0.1.33 g (7 mmol) of p-toluene sulfonic acid, and 15 g of anisole were put in a 100 mL round flask equipped with a condenser and stirred while heated up to perform a polymerization reaction at 150 °C. After performing the reaction for 38 hours, the polymerization reaction solution was cooled down to room temperature (23 °C to 25 °C) and diluted with 30 g of HBM (methyl 2-hydroxyisobutyrate) and then, added to 500 g of IPA. After stirring the mixture and allowing it to stand, a supernatant was removed therefrom. Subsequently, a purification process of diluting the purified resin layer with HBM (methyl 2-hydroxyisobutyrate) again, adding 500 g of IPA thereto, stirring the obtained mixture, and allowing it to stand was repeated four times to remove low molecules and catalysts. Finally, a polymer including a structural unit represented by Chemical Formula 1-2 (a molecular weight (Mw) = 8,100) was obtained.
[Chemical Formula 1-2]
Figure PCTKR2017013813-appb-I000004
Synthesis Example 3
15.7 g (0.06 mol) of 2,2',2''-((1,3,5-triazine-2,4,6-triyl)tris(oxy))triethanol, 12.96 g (0.05 mol) of 2,2'-((6-methoxy-1,3,5-triazine-2,4-diyl)bis(oxy))diacetic acid, 0.1.33 g (7 mmol) of p-toluene sulfonic acid, and 20 g of anisole were put in a 100 mL round flask equipped with a condenser and then, stirred by using a magnetic bar while heated up to 150 °C to perform a polymerization reaction. After performing the reaction for 22 hours, the polymerization reaction solution was cooled down to room temperature (23 °C to 25 °C) and diluted with 30 g of HBM (methyl 2-hydroxyisobutyrate) and then, added to 500 g of IPA. After stirring the mixture and allowing it to stand, a supernatant was removed therefrom. A purification process of diluting the purified resin layer again with HBM (methyl 2-hydroxyisobutyrate), adding 500 g of IPA thereto, stirring the obtained mixture, and allowing it to stand was repeated four times in total to remove low molecules and catalysts. Finally, a polymer including a structural unit represented by Chemical Formula 1-3 (a molecular weight (Mw) = 4,500) was obtained.
[Chemical Formula 1-3]
Figure PCTKR2017013813-appb-I000005
Synthesis Example 4
14.96 g (0.06 mol) of 2,4,6-triallyloxy-1,3,5-triazine, 3.77 g (0.04 mol) of 1,2-ethanedithiol, 7.81 g (0.1 mol) of 2-mercaptoethanol, 0.13 g (8 mmol) of AIBN, and 107 g of dimethyl formamide (DMF) were put in a 100 mL 2-necked round flask equipped with a condenser and then, mixed by using a magnetic bar at 80 °C. After performing a reaction for 6 hours, the reactant was cooled down to room temperature (23 °C to 25 °C) and added to an excessive amount of hexane. After stirring the mixture and allowing it to stand, a supernatant was removed therefrom. Subsequently, the reactant solution was added to toluene, and after stirring the obtained mixture and allowing it to stand, a supernatant was removed therefrom. In this way, the obtained reactant was purified after removing low molecules and catalysts to obtain a polymer including a structural unit represented by Chemical Formula 1-4 (a molecular weight (Mw) = 3,800).
[Chemical Formula 1-4]
Figure PCTKR2017013813-appb-I000006
Synthesis Example 5
3.6 g (20 mmol) of 2,4-dichloro-6-methoxy-1,3,5-triazine was put in a 250 mL round flask equipped with a condenser, and 20 mL of CH2Cl2 was added thereto to dissolve it. Subsequently, 2.4 g (60 mmol) of NaOH dissolved in 20 mL of water was added to the reaction vessel. 20 mg of TBAB with PTC was put in the reaction vessel, and then, a reaction was performed at room temperature (23 °C to 25 °C) for 8 hours. Only an organic layer was extracted from the reaction solution and then, dried and condensed to obtain a white solid. This solid was washed several times with hexane and was dried to finally obtain a polymer including a structural unit represented by Chemical Formula 1-5 (a molecular weight (Mw) = 3,200).
[Chemical Formula 1-5]
Figure PCTKR2017013813-appb-I000007
(Me is a methyl group)
Synthesis Example 6
4.95 g (126 mmol) of NaOH, 3.7 g (60 mmol) of ethanediol, and 80 mL of water were put in a 250 mL round flask equipped with a condenser. 0.0036 mmol of BnMe3NCl dissolved in 70 mL of water with PTC was added thereto. Subsequently, 7.38 g (40 mmol) of cyanuric chloride was dissolved in 100 mL of CH2Cl2, and the solution was added to the reaction vessel at 2 °C. A reaction was performed for 2 hours or so at the same temperature and then, for 1 hour by increasing the reaction temperature up to 15 °C and for 5 hours by increasing the temperature up to room temperature (23 °C to 25 °C). An additional amount of (3.7 g, 60 mmol) of ethanediol was added thereto. After stirring the mixture for 2 hours, an organic layer was separated from an aqueous layer and then, dried, and a solvent therein was removed. A viscous material remaining there was dried at 35 °C for 2 days and was washed with water and methanol. The obtained product was dissolved in acetone, the solution was precipitated in water and methanol, and a precipitate therein was dried to obtain a polymer including a structural unit represented by Chemical Formula 1-6 (a molecular weight (Mw) = 2,800).
[Chemical Formula 1-6]
Figure PCTKR2017013813-appb-I000008
Synthesis Example 7
4.95 g (126 mmol) of NaOH, 5.4 g (60 mmol) of butanediol, and 80 mL of water were put in a 250 mL flask equipped with a condenser. Subsequently, 0.0036 mmol of BnMe3NCl with PTC was dissolved in 70 mL of water, and the solution was added to this reaction solution. Then, 7.38 g (40 mmol) of cyanuric chloride was dissolved in 100 mL of CH2Cl2, and the obtained solution was added to the reaction vessel at 2 °C. A reaction was performed at the same temperature for about 2 hours and then, for 1 hour by increasing the reaction temperature up to 15 °C and for 5 hours by increasing the temperature up to room temperature (23 °C to 25 °C). 5.4 g (60 mmol) of butanediol was added thereto. The obtained mixture was further stirred for 2 hours and an organic layer was separated from an aqueous layer and dried, and a solvent was removed therefrom. A viscous material remaining there was washed with water and methanol at 35 °C for 2 days. The obtained material was dissolved in acetone, the solution was precipitated in water and methanol, and a precipitate therein was dried to finally obtain a polymer including a structural unit represented by Chemical Formula 1-7 (a molecular weight (Mw) = 5,600).
[Chemical Formula 1-7]
Figure PCTKR2017013813-appb-I000009
Comparative Synthesis Example 1
5.54 g of 2-thio methyl-4,6-diol-1,3,5-triazine, 10.00 g of monoallyl diglycidyl isocyanuric acid, and 0.40 g of benzyl triethyl ammonium chloride as a catalyst were added to 63.77 g of propylene glycol mono methylether, and the mixture was reacted under a reflux for 24 hours to obtain a polymer solution including a polymer including a structural unit represented by Chemical Formula 2 (a molecular weight (Mw) = 4,300).
[Chemical Formula 2]
Figure PCTKR2017013813-appb-I000010
Preparation of Resist Underlayer Composition
Example 1
The polymer prepared in Synthesis Example 1, PD1174 (TCI Inc.; hardener) (15 parts by weight based on 100 parts by weight of the polymer), and pyridinium p-toluenesulfonate (1 part by weight based on 100 parts by weight of the polymer) were dissolved in a mixed solvent of propylene glycol monomethylether and ethyllactate (a weight ratio = 1:1), and the solution was stirred for 6 hours to prepare a resist underlayer composition.
An amount of the mixed solvent was controlled, so that the polymer was included in a solid content of 2 wt% based on a total weight of the resist underlayer composition.
Examples 2 to 7
Each resist underlayer composition was prepared according to the same method as Example 1 except for using each polymer according to Synthesis Examples 2 to 7.
Comparative Example 1
A resist underlayer composition was prepared according to the same method as Example 1 except for using the polymer according to Comparative Synthesis Example 1.
Evaluation 1: Optical Properties
The compositions according to Examples 1 to 7 and Comparative Example 1 were respectively taken by 2 ㎖, applied on a 4 inch wafer, and spin-coated at 1,500 rpm for 20 seconds by using a spin coater (Mikasa Co., Ltd.). Subsequently, the coated compositions were cured at 230 °C for 90 seconds to respectively form 30 nm-thick thin layers. A refractive index (n) and an extinction coefficient (k) of each thin layer were measured under a condition of 800 A by using VASE Elliposmeters (J.A. Woollam Co.).
The results are shown in Table 1.
n k
Example 1 1.94 0.29
Example 2 1.92 0.28
Example 3 1.99 0.29
Example 4 1.95 0.31
Example 5 1.97 0.29
Example 6 1.91 0.31
Example 7 1.88 0.26
Comparative Example 1 1.96 0.39
Referring to Table 1, the refractive indices and extinction coefficients of the resist underlayer compositions according to Examples 1 to 7 were applicable as a resist underlayer at an ArF wavelength (193 nm and 248 nm), and thus a resist underlayer composition of the present invention turned out to have improved reflectance.
Evaluation 2: Coating Uniformity
Each composition according to Examples 1, 4, 6, and 7 and Comparative Example 1 was taken by 2 ㎖ and respectively applied on an 8-inch wafer and then, spin-coated at a main speed of 1,500 rpm for 20 seconds by using an auto track (ACT-8, TEL) and cured at 230 °C for 90 seconds to respectively form 300 nm-thick thin layers. Thicknesses of the thin layers horizontally at 51 points were measured to compare uniformity.
The results are shown in Table 2.
In Table 2, the smaller coating uniformity (%) is, the more improved it is.
Coating uniformity (%)
Example 1 2.1
Example 4 2.6
Example 6 1.9
Example 7 1.9
Comparative Example 1 3.3
Referring to Table 2, the resist underlayer compositions according to Examples 1, 4, and 6 showed improved coating uniformity compared with the resist underlayer composition according to Comparative Example 1.
While this invention has been described in connection with what is presently considered to be practical example embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims (9)

  1. A resist underlayer composition, comprising:
    a polymer including a moiety represented by Chemical Formula 1; and
    a solvent:
    [Chemical Formula 1]
    Figure PCTKR2017013813-appb-I000011
    wherein, in Chemical Formula 1,
    a is an integer of 0 to 3,
    when a is 0, R1 is hydrogen, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C1 to C30 heteroalkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkynyl group, or a combination thereof,
    when a is an integer of 1 to 3, R1 is a linking point (*), R0 is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
    R2 and R3 are independently a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C1 to C30 heteroalkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C1 to C30 alkenylene group, a substituted or unsubstituted C1 to C30 alkynylene group, ester (-COO-), ether (-CO-), -CS-, or a combination thereof,
    b and c are independently an integer of 0 to 3, and
    * is a linking point.
  2. The resist underlayer composition of claim 1, wherein in Chemical Formula 1, R2 and R3 independently include at least one ester (-COO-), ether (-CO-), or -CS- in the structure thereof or at least one substituted or unsubstituted C1 to C30 alkylene group, or a substituted or unsubstituted C1 to C30 heteroalkylene group in the structure thereof.
  3. The resist underlayer composition of claim 1, wherein in Chemical Formula 1, when a is 0, R1 is a C1 to C30 alkyl group, a C1 to C30 alkyl group substituted with at least one hydroxy group, a C1 to C30 heteroalkyl group, a C1 to C30 heteroalkyl group substituted with at least one hydroxy group, or a combination thereof, and
    in Chemical Formula 1, when a is 1, R0 includes at least one ester (-COO-), ether (-CO-), or -CS- in the structure thereof or
    at least one substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C1 to C30 alkylene group including a substituted or unsubstituted C1 to C30 heteroalkylene group, a C1 to C30 alkylene group substituted with at least one hydroxy group, or a C1 to C30 heteroalkylene group.
  4. The resist underlayer composition of claim 1, wherein a weight average molecular weight of the polymer is 1,000 to 100,000.
  5. The resist underlayer composition of claim 1, wherein the composition further comprises a cross-linking agent having at least two cross-linking sites.
  6. The resist underlayer composition of claim 1, wherein the composition further comprises an additive of a surfactant, a thermal acid generator, a plasticizer, or a combination thereof.
  7. A method of forming patterns, comprising:
    forming an etching subject layer on a substrate;
    coating the resist underlayer composition of claim 1 on the etching subject layer to form a resist underlayer;
    forming a photoresist pattern on the resist underlayer; and
    sequentially etching the resist underlayer and the etching subject layer using the photoresist pattern as an etching mask.
  8. The method of claim 7, wherein the step of forming the photoresist pattern comprises:
    forming a photoresist layer on the resist underlayer;
    exposing the photoresist layer; and
    developing the photoresist layer.
  9. The method of claim 7, wherein the step of forming the resist underlayer further comprises heat-treating the coated resist underlayer composition at a temperature of 100 °C to 500 °C.
PCT/KR2017/013813 2017-04-28 2017-11-29 Resist underlayer composition and method of forming patterns using the resist underlayer composition WO2018199419A1 (en)

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KR102400603B1 (en) 2019-03-29 2022-05-19 삼성에스디아이 주식회사 Resist underlayer composition, and method of forming patterns using the composition
KR102407824B1 (en) * 2019-11-18 2022-06-10 삼성에스디아이 주식회사 Resist underlayer composition, and method of forming patterns using the composition
KR102456166B1 (en) * 2020-03-17 2022-10-17 삼성에스디아이 주식회사 Resist underlayer composition, and method of forming patterns using the composition
KR102563287B1 (en) * 2020-08-12 2023-08-02 삼성에스디아이 주식회사 Resist underlayer composition, and method of forming patterns using the composition
KR102563289B1 (en) * 2020-08-12 2023-08-02 삼성에스디아이 주식회사 Resist underlayer composition, and method of forming patterns using the composition
KR102586108B1 (en) * 2020-11-09 2023-10-05 삼성에스디아이 주식회사 Resist underlayer composition, and method of forming patterns using the composition
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