US20100055408A1 - Organic anti-reflective layer composition containing ring-opened phthalic anhydride and method for preparation thereof - Google Patents

Organic anti-reflective layer composition containing ring-opened phthalic anhydride and method for preparation thereof Download PDF

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Publication number
US20100055408A1
US20100055408A1 US12/321,091 US32109109A US2010055408A1 US 20100055408 A1 US20100055408 A1 US 20100055408A1 US 32109109 A US32109109 A US 32109109A US 2010055408 A1 US2010055408 A1 US 2010055408A1
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substituted
unsubstituted
carbon atoms
reflective layer
group
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US12/321,091
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Inventor
Jong-Don Lee
Jun-Ho Lee
Shin-Hyo Bae
Seung-Hee Hong
Seung-Duk Cho
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Kumho Petrochemical Co Ltd
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Korea Kumho Petrochemical Co Ltd
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Assigned to KOREA KUMBO PETROCHEMICAL CO., LTD. reassignment KOREA KUMBO PETROCHEMICAL CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAE, SHIN-HYO, CHO, SEUNG-DUK, HONG, SEUNG-HEE, LEE, JONG-DON, LEE, JUN-HO
Publication of US20100055408A1 publication Critical patent/US20100055408A1/en
Priority to US13/186,101 priority Critical patent/US8357482B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/04—Saturated compounds having a carboxyl group bound to a three or four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24479—Structurally defined web or sheet [e.g., overall dimension, etc.] including variation in thickness
    • Y10T428/24612—Composite web or sheet

Definitions

  • the present invention relates to a novel light absorbent for forming an organic anti-reflective layer, which is a ring-opened phthalic anhydride compound, an organic anti-reflective layer composition, a method for patterning a semiconductor device using the organic anti-reflective layer composition, and a semiconductor device produced by the method for patterning.
  • the present invention relates to a novel light absorbent capable of being used in producing an organic anti-reflective layer which is useful for the formation of ultrafine semiconductor patterns using an ArF excimer laser; an organic anti-reflective layer composition containing the light absorbent, which prevents reflection from underneath film layers in lithographic processes, prevents a stationary wave, and exhibits a high dry etching rate; a method for patterning a semiconductor device using the organic anti-reflective layer composition; and a semiconductor device produced by the method for patterning.
  • A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group having 1 to 20 carbon atoms and containing one or more heteroatoms, a substituted or unsubstituted aromatic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3 to 20 carbon atoms, a substituted or unsubstituted alicyclic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroalicyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ether having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfoxide having 3 to 20 carbon atoms,
  • A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group having 1 to 20 carbon atoms and containing one or more heteroatoms, a substituted or unsubstituted aromatic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3 to 20 carbon atoms, a substituted or unsubstituted alicyclic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroalicyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ether having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfoxide having 3 to 20 carbon atoms,
  • an organic anti-reflective composition comprising the light absorbent represented by the formula 1 or formula 2, a polymer, a thermal acid generating agent, a crosslinking agent, and a solvent.
  • a method for patterning a semiconductor device comprising:
  • the organic anti-reflective layer composition according to the present invention exhibits excellent adhesiveness and storage stability, as well as excellent resolution in both C/H patterns and L/S patterns.
  • the organic anti-reflective layer composition also has an excellent process window, so that excellent pattern profiles can be obtained irrespective of the type of the substrate.
  • etching of the anti-reflective layer can be rapidly carried out in ultrafine patterning processes making use of a 193-nm light source, and as a result, development of high integration semiconductor devices can be achieved more actively.
  • FIG. 1 is a 1 H-NMR spectrum of a copolymer produced according to an embodiment of the present invention
  • FIG. 3 is a 1 H-NMR spectrum of a copolymer produced according to another embodiment of the present invention.
  • FIG. 5 is a 1 H-NMR spectrum of a copolymer produced according to another embodiment of the present invention.
  • FIG. 6 is a 1 H-NMR spectrum of a copolymer produced according to another embodiment of the present invention.
  • FIG. 7 is a 1 H-NMR spectrum of a copolymer produced according to another embodiment of the present invention.
  • FIG. 8 is a 1 H-NMR spectrum of a copolymer produced according to another embodiment of the present invention.
  • FIG. 9 is a 1 H-NMR spectrum of a copolymer produced according to another embodiment of the present invention.
  • a ring-opened phthalic anhydride represented by the following formula 1, which serves as a light absorbent for forming an organic anti-reflective layer, is provided.
  • the compound of formula 2 has a weight average molecular weight of 350 to 100,000, and more preferably 400 to 50,000.
  • the light absorbent of the present invention includes a benzene chromophore, and contains functional groups for thermal curing.
  • a carboxylic acid functional group is generated by ring-opening of the light absorbent by means of an alcohol compound, and this carboxylic acid functional group reacts with a functional group of the thermally curable compound, such as acetal, epoxy or hemiacetal, to form a crosslinked structure.
  • substituted means that one or more hydrogen atoms in a group may be respectively substituted with a halogen atom, a hydroxyl group, a nitro group, a cyano group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkenyl group, a C 1 -C 10 alkynyl group, a C 6 -C 20 aryl group, a C 7 -C 20 arylalkyl group, a C 4 -C 20 heteroaryl group or a C 5 -C 20 heteroarylalkyl group.
  • the compounds represented by formula 1 of the present invention are produced by reacting a substituted or unsubstituted benzyl alcohol compound represented by the following formula 61 with various dianhydride compounds in the presence of a base, and then neutralizing the base used with an acid.
  • R 4 represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group.
  • R 5 represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group.
  • the light absorbent of the present invention can be synthesized by conventional methods, but preferably, synthesis of the light absorbent of the present invention is achieved by a reaction in a basic environment.
  • the aforementioned various dianhydrides are advantageous in that the compounds are highly reactive with alcohols, and have four reactive groups so that two chromophores can be introduced first and then two more crosslinking sites can be provided in the subsequent processes.
  • Examples of the base that can be used to provide a basic environment include dimethylaminopyridine, pyridine, 1,4-diazabicyclo[2,2,2]octane. 1,5-diazabicyclo[4,3,0]nonane, triethylamine, 2,6-di-tert-butylpyridine, diisopropylethylamine, diazabicycloundecene, tetramethylethylenediamine, tetrabutylammonium bromide and the like, and no particular limitation is posed.
  • the temperature for synthesis of the compound can be selected and used in accordance with the solvent, and is usually 5° C. to 200° C., and preferably 20° C. to 100° C.
  • an organic anti-reflective layer composition containing the light absorbent of the present invention is also provided.
  • the anti-reflective layer should be able to be etched more rapidly than the photoresist layer on the upper side, so that the loss of photoresist resulting from etching of underneath film layers can be reduced.
  • organic anti-reflective layer composition according to the present invention will be described in detail.
  • An organic anti-reflective layer employing such polymer acquires resistance to dissolution by solvents, as the composition applied on a substrate is cured while going through a baking process.
  • the crosslinking agent is preferably a compound having at least two or more crosslinkable functional groups, and examples thereof include aminoplastic compounds, polyfunctional epoxy resins, mixtures of dianhydrides, and the like.
  • the aminoplastic compounds may be exemplified by dimethoxymethylglycoluril, diethoxymethylglycoluril and mixtures thereof, diethyldimethylmethylglycoluril, tetramethoxymethylglycoluril, hexamethoxymethylmelamine resin, and the like.
  • thermal acid generating agent As a catalyst for accelerating the curing reaction, it is preferable to use a thermal acid generating agent as a catalyst for accelerating the curing reaction.
  • a thermal acid generating agent to be contained in the present invention, toluenesulfonic acid, amine salts or pyridine salts of toluenesulfonic acid, alkylsulfonic acid, amine salts or pyridine salts of alkylsulfonic acid, and the like can also be used.
  • organic solvent that can be used in the organic anti-reflective layer composition of the present invention
  • one or more solvents selected from the group consisting of propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, ethyl lactate, propylene glycol n-propyl ether, dimethylformamide (DMF), ⁇ -butyrolactone, ethoxyethanol, methoxyethanol, methyl 3-methoxypropionate (MMP) and ethyl 3-ethoxypropionate (EEP).
  • PGME propylene glycol monomethyl ether
  • PMEA propylene glycol monomethyl ether acetate
  • DMF dimethylformamide
  • MMP methyl 3-methoxypropionate
  • EEP ethyl 3-ethoxypropionate
  • the organic anti-reflective layer composition contains the light absorbent represented by formula 1 or formula 2 in an amount of preferably 0.1 to 40% by weight, more preferably 0.1 to 15% by weight, and even more preferably 0.1 to 10% by weight, based on the whole composition.
  • the polymer is contained in an amount of preferably 0.1 to 20% by weight based on the whole composition.
  • the crosslinking agent is contained in an amount of preferably 0.01 to 15% by weight, and more preferably 0.05 to 7% by weight, based on the whole composition.
  • the thermal acid generating agent is contained in an amount of 0.01 to 20% by weight, more preferably 0.01 to 10% by weight, and even more preferably 0.02 to 5% by weight, based on the whole composition.
  • the balance of the contents in the composition can be constituted of the solvent and other additional additives which are well known and widely used.
  • the method for forming a pattern of a semiconductor device using the organic anti-reflective layer composition as described above comprises applying the organic anti-reflective layer composition on top of a layer to be etched; curing the applied composition through a baking process, and forming crosslinking bonds to form an organic anti-reflective layer; applying a photoresist on top of the organic anti-reflective layer, and exposing and developing the photoresist to form a photoresist pattern; and etching the organic anti-reflective layer using the photoresist pattern as an etching mask, and then etching the layer to be etched so as to pattern the layer to be etched.
  • the baking process can be carried out preferably at a temperature of 150° C. to 250° C. for 0.5 to 5 minutes, and more preferably for 1 minute to 5 minutes.
  • an additional baking process can be carried out again before or after laminating an organic or inorganic composition of anti-reflective layer or silicone anti-reflective layer on top of a spin-on carbon hard mask, and such baking process is preferably carried out at a temperature of 70° C. to 200° C.
  • a semiconductor device produced by the patterning method of the present invention is provided.
  • the separated organic layer was subjected to solvent removal, and then was dissolved in propylene glycol monomethyl ether acetate, to obtain a compound.
  • the 1 H-NMR spectrum of the solid light absorbent produced according to Synthesis Example 8 is presented in FIG. 8 .
  • Each of the organic anti-reflective layer compositions A to J prepared in Example 1 to 10 was applied on a silicon wafer by spin coating, and then the coated wafer was baked on a hot plate at 230° C. for 1 minute to form an organic anti-reflective layer. The thickness of the layer was measured, and the wafer coated with the organic anti-reflective layer was immersed for 1 minute in ethyl lactate and propylene glycol monomethyl ether, which are solvents used for the photoresist. Subsequently, the coated wafer was baked on a hot plate at 100° C. for 1 minute to completely remove the solvents, and then the thickness of the organic anti-reflective layer was measured again. It was confirmed that the anti-reflective layer was insoluble in the solvents.
  • Each of the organic anti-reflective layer compositions A to J prepared in Example 1 to 10 was applied on a silicon wafer by spin coating, and then the coated wafer was baked on a hot plate at 230° C. for 1 minute to form an organic anti-reflective layer.
  • the refractive index (n) at 193 nm and the extinction coefficient (k) of the anti-reflective layer were measured using a spectroscopic ellipsometer (J.A. Woollam Co., Inc.). The measurement results are presented in Table 1.
  • An organic anti-reflective layer was formed using each of the organic anti-reflective layer compositions A to J prepared in Example 1 to 10, and then the refractive index (n) at 193 nm and the extinction coefficient (k) of the anti-reflective layer were measured using a spectroscopic ellipsometer. Subsequently, the thickness of the first microthin film, and the reflectance in the case of using the thickness of the first microthin film were calculated by performing a simulation using the values of the refractive index (n) and extinction coefficient (k) obtained from the measurement. The simulation was related to the reflectance obtainable in the case where 40 nm of silicon oxynitride was deposited on the silicon wafer. The software used in the simulation was KLA Tencor FINDLE Division PROLITH, and the results are presented in Table 1.
  • Each of the organic anti-reflective layer compositions A to J prepared in Example 1 to 10 was applied by spin coating on a silicon wafer deposited with silicon oxynitride, and then the coated wafer was baked on a hot plate at 230° C. for 1 minute, to form an organic anti-reflective layer. Subsequently, an ArF photoresist was applied on top of the organic anti-reflective layer, and then the coated wafer was baked at 100° C. for 60 seconds. Then, the photoresist was exposed using a scanner equipment, and then the wafer was baked again at 115° C. for 60 seconds. The exposed wafer was developed using a developer solution containing 2.38% by weight of TMAH, to obtain a final photoresist pattern. The pattern was of L/S type with a size of 80 nm, and the results are presented in Table 2.

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JP2010055049A (ja) 2010-03-11
CN101659615A (zh) 2010-03-03
TWI443123B (zh) 2014-07-01
KR100997502B1 (ko) 2010-11-30
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US20110272643A1 (en) 2011-11-10
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