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WO2018088673A1 - Polymère, composition de film organique, et procédé de formation de motif - Google Patents

Polymère, composition de film organique, et procédé de formation de motif Download PDF

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Publication number
WO2018088673A1
WO2018088673A1 PCT/KR2017/007906 KR2017007906W WO2018088673A1 WO 2018088673 A1 WO2018088673 A1 WO 2018088673A1 KR 2017007906 W KR2017007906 W KR 2017007906W WO 2018088673 A1 WO2018088673 A1 WO 2018088673A1
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Prior art keywords
substituted
unsubstituted
group
formula
polymer
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English (en)
Korean (ko)
Inventor
정현일
김성환
김성현
박유신
임재범
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Samsung SDI Co Ltd
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Samsung SDI Co Ltd
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Priority claimed from KR1020170055623A external-priority patent/KR102037818B1/ko
Application filed by Samsung SDI Co Ltd filed Critical Samsung SDI Co Ltd
Priority to CN201780069472.4A priority Critical patent/CN109983053A/zh
Priority to US16/339,451 priority patent/US11203662B2/en
Priority to JP2019524024A priority patent/JP7025422B2/ja
Priority to EP17868972.5A priority patent/EP3521332A4/fr
Publication of WO2018088673A1 publication Critical patent/WO2018088673A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • 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
    • 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
    • H10P76/00—
    • H10P76/40—

Definitions

  • a novel polymer, an organic film composition containing the polymer, and a pattern forming method using the organic film composition is provided.
  • a typical lithographic technique involves forming a material layer on a semiconductor substrate, coating a photoresist layer thereon, exposing and developing a photoresist pattern, and then etching the material layer using the photoresist pattern as a mask. do.
  • a fine pattern may be formed by forming an organic film called a hardmask layer between the material layer and the photoresist layer to be etched.
  • 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 the characteristics of heat resistance and etching resistance to withstand the multiple etching process.
  • the hard mask layer has recently been proposed to form by spin-on coating (spin-on coat ing) method instead of chemical vapor deposition method.
  • the spin-on coating method is easy to process and can improve gap-fill properties and planarization properties.
  • multiple pattern formation is essential.
  • a buried property of filling the film with a film without voids is required.
  • One embodiment provides a novel polymer that ensures solubility and yet has excellent heat and etching resistance.
  • Another embodiment provides an organic film composition comprising the polymer. Another embodiment provides a pattern forming method using the organic film composition.
  • a polymer comprising a structural unit represented by the following Chemical Formula 1, and a structural unit represented by the following Chemical Formula 2 is provided. '
  • a 1 is a moiety represented by the following formula (X),
  • a 2 is a substituted or unsubstituted C 6 to C 30 aromatic ring which is different from A 1.
  • B 1 and B 2 are each independently a substituted or unsubstituted C6 to C30 aromatic ring,
  • Ar is a substituted or unsubstituted square ring, a substituted or unsubstituted pentagonal ring, a substituted or unsubstituted hexagonal ring, or a fused ring thereof
  • R a is hydrogen, a hydroxy group, a halogen group, a substituted or Unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted C6 to C30 aryl Group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
  • Z a is each independently a hydroxy group, a halogen group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to A C30 alkynyl group substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
  • n 0 or 1
  • B 1 and B 2 may each be any one of the substituted or unsubstituted moieties listed in Group 1 below.
  • a 1 may be any one of the moieties listed in Group 2 below.
  • R 1 and R 2 are each independently hydrogen, hydroxy group, halogen group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or Unsubstituted C2 To C30 alkynyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroalkyl group, substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof:
  • hydrogen in each moiety is each independently a hydroxy group, a halogen group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 Alkenyl groups, substituted or unsubstituted C2 to C30 alkynyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C1 to C30 heteroalkyl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, or these It is substituted by a combination of or unsubstituted.
  • a 2 may be any one of the substituted or unsubstituted moieties listed in Group 1.
  • ⁇ In Formula 2 may be substituted with at least one hydroxy group.
  • B 1 and B 2 may have the same structure as the substituted or unsubstituted C6 to C30 aromatic ring.
  • the weight average molecular weight of the polymer may be 1, 000 to 200, 000.
  • an organic film composition including the polymer described above and a solvent is provided.
  • the polymer may be included in an amount of 0.01 wt% to 50 wt% with respect to the total content of the organic layer composition.
  • forming a material layer on a substrate applying an organic film composition comprising the above-described polymer and solvent on the material layer, heat treating the organic film composition to form a hard mask layer
  • Forming a photoresist layer on the hard mask layer forming a photoresist layer on the silicon-containing thin film layer; exposing and developing the photoresist layer to form a photoresist pattern;
  • Selectively removing the silicon containing thin film layer and the hardmask layer, exposing a portion of the material layer, and etching the exposed portion of the material layer It provides a formation method.
  • the applying of 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 polymer according to one embodiment is excellent in heat resistance and etching resistance.
  • the polymer is used as an organic film material, it is possible to provide an organic film that can satisfy flatness while having excellent film density and etching resistance.
  • FIG. 1 is a flowchart illustrating a pattern forming method according to an embodiment.
  • the 1-substituted ' is a hydrogen atom a halogen atom in the compound (F, Br, C1, or 1), a hydroxy group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido, amino Dino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, C1 to C30 alkyl group, C2 to C30 alkenyl group, C2 C30 to C30 alkynyl group, C6 to C30 aryl group, C7 to C30 arylalkyl group, C1 to C30 alkoxy group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, C3 to C30 cycloalkyl group, C3 to C15 cycl
  • hetero means containing 1 to 3 heteroatoms selected from N, 0, S and P.
  • hetero indicates a point of connection of a compound or compound moiety.
  • the polymer according to one embodiment includes a structural unit represented by the following Chemical Formula 1, and a structural unit represented by the following Chemical Formula 2.
  • a 1 is a moiety represented by the following formula (X),
  • a 2 is a substituted or unsubstituted C 6 to C 30 aromatic ring having a structure with A 1 ,
  • B 1 and B 2 are each independently a substituted or unsubstituted C6 to C30 aromatic ring,
  • Ar is a substituted or unsubstituted square ring, a substituted or unsubstituted pentagonal ring substituted or unsubstituted hexagonal ring, or a fused ring thereof
  • R a is hydrogen, a hydroxy group, a halogen group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 An alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
  • Z a is each independently a hydroxy group, a halogen group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to A C30 alkynyl group substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
  • n 0 or 1
  • the polymer includes both the structural units represented by Chemical Formula 1 and the structural units represented by Chemical Formula 2, wherein the number and arrangement of these structural units are not limited.
  • the structural units represented by Formulas 1 and 2 consist of one part represented by A 1 and A 2 , and a second part represented by hydrogen atom (H), carbon, B 1 and B 2 .
  • a 1 and A 2 have different structures.
  • a 1 is represented by Formula X as an indol compound, or a derivative thereof.
  • Ar represents a substituted or unsubstituted square ring, a substituted or unsubstituted pentagonal ring, a substituted or unsubstituted hexagonal ring, or a fused ring thereof, wherein the fused ring is, for example, benzene
  • the ring may be in two, three or four fused form, but is not limited thereto.
  • a 1 may be, for example, any one of the moieties listed in Group 2, but is not limited thereto.
  • R 1 and R 2 are each independently hydrogen, hydroxy group, halogen group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or Unsubstituted C2 To C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof:
  • hydrogen in each moiety is each independently a hydroxy group, a halogen group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 Alkenyl groups, substituted or unsubstituted C2 to C30 alkynyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C1 to C30 heteroalkyl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, or these It is substituted by a combination of or unsubstituted.
  • the position at which each moiety is linked to Formula 1 in Group 2 is not particularly limited.
  • the polymer can be easily controlled by selecting the type and number of Z 1 to Z 7 representing a functional group substituted with a cyclic group.
  • a 2 has a structure different from A 1 representing indole, or a derivative thereof, as a substituted or unsubstituted aromatic ring of C6 to C30.
  • a 2 may be any one of the substituted or unsubstituted moieties listed in Group 1 below, but is not limited thereto.
  • the position at which each moiety is linked to Formula 2 in Group 1 is not particularly limited.
  • at least one hydrogen in the moiety is a hydroxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alke. It may be a form substituted by a silyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a combination thereof.
  • the A 2 May be substituted by at least one hydroxy group.
  • the polymers can be secured etch-resistant, having a cyclic group portion is represented by A 1, and A 2 in the general formula (2) in formula (I).
  • the polymer includes an indole moiety (A 1 ) in the structural unit represented by Chemical Formula 1, whereby one side of the pentagonal ring moiety containing a nitrogen atom (N) has a structure (fused) blocked by a ring. The branches but the other side By having an open structure without fusion (ie, one side of the pentagonal ring in Formula X is fused with Ar, the other side is not), the pentagonal ring portion containing the nitrogen atom is baked compared to the blocked carbazole series.
  • the inside of the polymer or the bond between the polymers may be promoted to have an effect of increasing the carbon content, and thus the etching resistance may be further improved.
  • the structural units represented by Chemical Formulas 1 and 2 include a hydrogen atom (H), carbon, a second portion represented by B 1 and B 2 .
  • B 1 and B 2 may be any one of the substituted or unsubstituted moieties listed in the following Group 1, but is not limited thereto.
  • B 1 and B 2 may have the same structure. Since the polymer basically includes a carbon ring group represented by A 1 , A 2 , B 1, and B 2 , etching resistance can be ensured.
  • the carbon contained in the crab 2 corresponds to 'tertiary carbon'.
  • the tertiary carbon refers to carbon in a form in which three sites of four hydrogens bonded to carbon are substituted with a group other than hydrogen.
  • the ring parameter of the polymer may be maximized to further enhance the etching resistance.
  • the solubility of the hard mask layer may be improved, which is advantageous to apply to the spin-on coating method.
  • the polymer can be polymerized, for example, by terpolymerization.
  • the tertiary carbon structure in the polymer can be formed, for example, by introducing an aldehyde compound, or derivative thereof, as an electrophile in the synthesis of the polymer.
  • the polymer has a structure that reduces the number of hydrogen present in the bonding position while increasing the carbon content of the polymer by using the aldehyde compound or a derivative thereof, and a monomer having a high carbon content in the ternary copolymerization. This can be enhanced.
  • the polymer may have a weight average molecular weight of about 500 to 200,000. More specifically, the polymer may have a weight average molecular weight of about 1, 000 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 is used as an organic film material, it is possible to form a uniform thin film without formation of pin-holes and voids or deterioration of thickness distribution during the baking process, as well as when a step is present in the lower substrate (or film) or pattern It can provide excellent gap-fill and planarization properties when forming a.
  • an organic film composition including the polymer described above and a solvent is provided.
  • the solvent is not particularly limited as long as it has sufficient solubility or dispersibility in the polymer, for example, propylene glycol, Propylene glycol diacetate, methoxy propanediol, diethylene glycol, diethylene glycol butyl ether, tri (ethylene glycol) monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclonucleanone, ethyl lactate At least one selected from gamma-butyrolactone, ⁇ , ⁇ -dimethylformamide, ⁇ , ⁇ -dimethylacetamide, methylpyridone, methylpyridinone, acetylacetone and ethyl 3-ethoxypropionate It may include.
  • the polymer is about 0.1% to 50% by weight, based on the total content of the organic film composition, about 0. 1 to 30 weight percent, or about 0. It may be included in 1 to 15% by weight. By including the polymer in the above range it is 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.
  • the surfactant may be, for example, fluoroalkyl-based compounds, alkylbenzenesulfonic acid salts, alkylpyridinium salts, polyethylene glycol, quaternary ammonium salts and the like, but is not limited thereto.
  • the crosslinking agent may be, for example, melamine type, substituted element type, or these polymer type.
  • a crosslinking agent having at least two crosslinking substituents for example, methoxymethylated glycoryl, subspecific methylated glycoryl, methoxymethylated melamine, appendoxymethylated melamine, methoxymethylated benzoguanamine, butoxy Compounds such as methylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, or subspecific methylated 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, an acidic compound such as ⁇ -luluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium ⁇ —lurusulsulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthalenecarboxylic acid, and / or 2 , 4,4,6- Tetrabromocyclohexadienone, benzointosylate, 2-nitrobenzyltosylate, and other alkyl sulfonic acid alkyl esters may be used, but is not limited thereto.
  • an acidic compound such as ⁇ -luluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium ⁇ —lurusulsulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzo
  • 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.
  • an organic film prepared using the organic film composition described above is provided.
  • the organic layer may be in the form of the organic layer composition, for example, coated on a substrate and then cured through a heat treatment process, and may include, for example, an organic thin film used in an electronic device such as a hard mask layer, a planarization layer, a regenerative layer, a layer release agent, and the like. can do.
  • a pattern forming method includes forming a material layer on a substrate (S1), applying an organic film composition including the polymer and a solvent on the material layer (S2), and heat treating the organic film composition. Forming a hard mask layer (S3), forming a silicon-containing thin film layer on the hard mask layer (S4), forming a photoresist layer on the silicon-containing thin film layer (S5), and exposing the photoresist 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 ⁇ , ⁇ .
  • the heat treatment of the organic film composition is, for example, about 100 to about 100
  • 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 layer 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.
  • the heat treatment may be performed at about 100 to 700 ° C. after the exposure.
  • Etching the exposed portion of the material layer may be performed by dry etching using an etching gas, and the etching gas may use, for example, CHF 3 ) CF 4) Cl 2) BC1 3 and combinations 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 internal silver is lowered to 60-70 ° C, and then 300 g of tetrahydrofuran is added to make the compound not hardened.
  • the pH of the compound is increased to 5-6 with 7% aqueous sodium bicarbonate solution.
  • 1000 ml of ethyl acetate was poured and stirring continued, and then the organic layer was extracted using a separatory funnel.
  • 500 ml of water is added to a separatory funnel, shaken to remove the remaining acid and sodium salt three or more times, and the organic layer is finally extracted.
  • the organic solution was concentrated by an evaporator, and 1 L of tetrahydrofuran was added to the obtained compound to obtain a solution.
  • the solution was slowly added dropwise to a beaker containing 5 L of the nucleic acid being stirred to form a precipitate to obtain a polymer including the structural units represented by the formula la.
  • the weight average molecular weight (Mw) and the polydispersity (PD) of the polymer obtained by gel permeation chromatography (GPC) were measured, and the weight average molecular weight (Mw) was 1,890. (Polydispersity, PD) was 1.35.
  • the weight average molecular weight (Mw) of the obtained polymer was 3,100, and polydispersity (PD) was 1.43. 2a]
  • the weight average molecular weight (Mw) of the obtained polymer was 2,140, and polydispersity (PD) was 1.32.
  • the weight average molecular weight (Mw) of the obtained polymer was 2,470, and polydispersity (PD) was 1.29.
  • a polymer comprising the structural units shown in Chemical Formula 5a was obtained using the same method as in Synthesis Example 1, except that 1-nap was used instead of phenanthren-9-ol (Phenanthren® 9-ol).
  • the weight average molecular weight (Mw) of the obtained polymer was 1,760, and polydispersity (Polydi spersi ty, PD) was 1.43.
  • the weight average molecular weight (Mw) of the obtained polymer was 2,410, and polydispersity (Polydi spersi ty, PD) was 1.55.
  • the weight average molecular weight (Mw) of the obtained polymer was 1,570, and polydispersity (Polydi spersi ty, PD) was 1.26.
  • the weight average molecular weight (Mw) of the obtained polymer was 1,940, and polydispersity (Polydi spersi ty, PD) was 1.35.
  • Polydispersity (PD) was 1.31.
  • the increase average molecular weight (Mw) of the obtained polymer was 1,920, and polydispersity (Polydi spersi ty, PD) was 1.34.
  • the weight average molecular weight (Mw) of the obtained polymer was 3,200, and polydispersity (Polydi spers i ty, PD) was 1.85.
  • the weight average molecular weight (Mw) of the obtained polymer was 2,680, and polydispersity (PD) was 1.56.
  • Synthesis Example 4 was synthesized using the same method as in Synthesis Example 4, except that [2,3-b] carbazole (1,3-dihydroindolo [2,3-b] carbazole was used as 1,3-dihydroindo instead of indole. A polymer was obtained comprising the structural units indicated.
  • the weight average molecular weight (Mw) of the obtained polymer was 4,620, and polydispersity (PD) was 1.73.
  • the polymer obtained in Synthesis Example 1 was dissolved in a mixed solvent of propylene glycol monomethyl ether acetate (PGMEA) and cyclohexanone (7: 3 (v / v)), followed by 0.1 Teflon. Filtration with a filter produced a hardmask composition. According to the desired thickness, the weight of the polymer was adjusted to 5.0 to 30.0 wt% based on the total weight of the hard mask composition.
  • PGMEA propylene glycol monomethyl ether acetate
  • cyclohexanone 7: 3 (v / v)
  • a hardmask supernatant was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 2 was used instead of the polymer obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 3 was used instead of the compound obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 4 was used instead of the polymer obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 6 was used instead of the polymer obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 7 was used instead of the polymer obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 8 was used instead of the polymer obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 9 was used instead of the polymer obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Synthesis Example 10 was used instead of the polymer obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Comparative Synthesis Example 1 was used instead of the polymer obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Comparative Synthesis Example 2 was used instead of the polymer obtained in Synthesis Example 1. Comparative Example 3
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Comparative Synthesis Example 3 was used instead of the polymer obtained in Synthesis Example 1.
  • a hardmask composition was prepared in the same manner as in Example 1, except that the compound obtained in Comparative Synthesis Example 4 was used instead of the polymer obtained in Synthesis Example 1. 3 ⁇ 4>
  • the hard mask compositions according to Examples 1 to 10 and Comparative Examples 1 to 4 were spin-on coated on the silicon wafer to a thickness of 4,000 A, and then heat-treated at 240 ° C. on a hot plate for 1 minute to form a thin film.
  • the thickness of the thin film was measured. Then on the thin film
  • Example 4 24.6 24.9 Example 5 26.2 24.8 Example 6 25.4 23. 1 Example 7 22.9 22.7 Example 8 22.5 22.4 Example 9 22.3 21.9 Example 10 26.9 25.0 Comparative Example 1 29.4 28.4 Comparative Example 2 28.7 29.5 Comparative Example 3 30.2 27.7 Comparative Example 4 29.4 27.5
  • the etch rate was recalculated by changing the heat treatment temperature and time to 400 ° C. and 2 minutes, respectively. The results are shown in Table 2.
  • Example 9 23.3 21.5
  • Example 10 28. 1 23.9 Comparative Example 1 31. 1 27.0 Comparative Example 2 30.2 26.6 Comparative Example 3 31.4 26.4 Comparative Example 4 30.7 25.5
  • the hardware according to Examples 1 to 10 Compared with the thin film formed from the hard mask compositions according to Comparative Examples 1 to 4, the thin film formed from the mask composition may have sufficient etching resistance against the etching gas, thereby improving bulk etch characteristics.
  • Evaluation 2 film density
  • a hard mask composition according to Examples 1 to 10 and Comparative Examples 1 to 4 was spin-on coated on a silicon wafer and heat-treated at 240 ° C. for 1 minute on a hot plate to form a thin film having a thickness of 1,000 A.
  • FIG. 1 A hard mask composition according to Examples 1 to 10 and Comparative Examples 1 to 4 was spin-on coated on a silicon wafer and heat-treated at 240 ° C. for 1 minute on a hot plate to form a thin film having a thickness of 1,000 A.
  • the film density of the thin film was measured using an X-ray diffraction analysis (X-ray diffraction ion) equipment of PANalyt i cal.
  • Comparative Example 4 1.24 Referring to Table 3, it can be seen that the thin film formed from the hard mask composition according to Examples 1 to 10 has a high level of film density compared with the thin films according to Comparative Examples 1 to 4.

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Abstract

La présente invention concerne : un polymère comprenant un motif structural représenté par la formule chimique 1 et un motif structural représenté par la formule chimique 2 ; une composition de film organique contenant le polymère ; et un procédé de formation d'un motif à l'aide de la composition de film organique. La définition des formules chimiques 1 et 2 est la même que celle décrite dans la description.
PCT/KR2017/007906 2016-11-10 2017-07-21 Polymère, composition de film organique, et procédé de formation de motif Ceased WO2018088673A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201780069472.4A CN109983053A (zh) 2016-11-10 2017-07-21 聚合物、有机膜组成物以及形成图案的方法
US16/339,451 US11203662B2 (en) 2016-11-10 2017-07-21 Polymer, organic layer composition, and method of forming patterns
JP2019524024A JP7025422B2 (ja) 2016-11-10 2017-07-21 重合体、有機膜組成物およびパターン形成方法
EP17868972.5A EP3521332A4 (fr) 2016-11-10 2017-07-21 Polymère, composition de film organique, et procédé de formation de motif

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KR20160149859 2016-11-10
KR10-2016-0149859 2016-11-10
KR10-2017-0055623 2017-04-28
KR1020170055623A KR102037818B1 (ko) 2016-11-10 2017-04-28 중합체, 유기막 조성물 및 패턴형성방법

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KR20190142730A (ko) * 2018-06-18 2019-12-27 도오꾜오까고오교 가부시끼가이샤 레지스트 조성물 및 레지스트 패턴 형성 방법
CN110850683A (zh) * 2018-08-20 2020-02-28 东友精细化工有限公司 硬掩模用组合物
US11220570B2 (en) * 2018-12-26 2022-01-11 Samsung Sdi Co., Ltd. Polymer, hardmask composition, and method of forming patterns
KR20220090193A (ko) * 2020-12-22 2022-06-29 삼성에스디아이 주식회사 하드마스크 조성물 및 패턴 형성 방법

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KR20170045592A (ko) * 2015-10-19 2017-04-27 삼성에스디아이 주식회사 중합체, 유기막 조성물, 및 패턴형성방법

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US20150044876A1 (en) * 2012-03-27 2015-02-12 Nissan Chemical Industries, Ltd. Resist underlayer film forming composition containing phenylindole-containing novolac resin
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KR20190142730A (ko) * 2018-06-18 2019-12-27 도오꾜오까고오교 가부시끼가이샤 레지스트 조성물 및 레지스트 패턴 형성 방법
KR102744955B1 (ko) 2018-06-18 2024-12-19 도오꾜오까고오교 가부시끼가이샤 레지스트 조성물 및 레지스트 패턴 형성 방법
CN110850683A (zh) * 2018-08-20 2020-02-28 东友精细化工有限公司 硬掩模用组合物
US11220570B2 (en) * 2018-12-26 2022-01-11 Samsung Sdi Co., Ltd. Polymer, hardmask composition, and method of forming patterns
KR20220090193A (ko) * 2020-12-22 2022-06-29 삼성에스디아이 주식회사 하드마스크 조성물 및 패턴 형성 방법
KR102676706B1 (ko) 2020-12-22 2024-06-18 삼성에스디아이 주식회사 하드마스크 조성물 및 패턴 형성 방법

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