USRE38282E1 - Process for using bilayer photoresist - Google Patents
Process for using bilayer photoresist Download PDFInfo
- Publication number
- USRE38282E1 USRE38282E1 US09/895,624 US89562401A USRE38282E US RE38282 E1 USRE38282 E1 US RE38282E1 US 89562401 A US89562401 A US 89562401A US RE38282 E USRE38282 E US RE38282E
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- polymer
- alkyl
- silylethoxy
- acid
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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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
- G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
Definitions
- the present invention relates to an improved bilayer photoresist and process for its use in lithography for manufacturing semiconductor devices.
- Bilayer resists generally comprise a top thin film imaging layer coated on a thick organic underlayer.
- the resist is patterned by: (i) imagewise exposure and development of the top layer, and then (ii) anisotropically transferring the developed pattern in the top layer through the thick underlayer to the substrate.
- the top layer contains precursors to refractory oxides such as silicon, boron, or germanium which enable the use of oxygen-reactive ion etching (RIE) in the image transfer step.
- RIE oxygen-reactive ion etching
- Bilayer resists are known in the art. However, these resists were generally developed before the advent of deep U.V. lithography (e.g., 248 nm and 193 nm) and are of little utility for high-resolution imaging. For example, in the review article “Polymeric Silicon-containing Resist Materials”, Advanced Material for Optics and Electronics, Vol. 4, pp. 95-127 (1994), there is disclosed on page 112 a positive bilayer resist having a top layer comprising the copolymer poly(co-trimethylsilylmethyl methacrylate and monooximido ⁇ diketone). The top layer is imaged by radiation chain scission and the image is transferred with oxygen R.I.E. However, the resist is not commercially viable due to slow photospeed and other resist performance problems. Therefore, there still is a need in the art for a bilayer photoresist suitable for commercial use.
- the present invention relates to a process for forming bilayer resist images on a substrate with a chemically-amplified, radiation-sensitive bilayer resist.
- the bilayer resist is disposed on a substrate and comprises (i) a top imaging layer comprising a radiation-sensitive acid generator and a vinyl polymer or copolymer formed by the polymerization of monomers, including one or more monomers selected from acrylate, methacrylate, hydroxystyrene (optionally substituted with C 1-6 alkyl), and C 5-20 cyclic olefin monomers, where preferably the polymer has an acid-cleavable silylethoxy group; and (ii) an organic underlayer.
- the present invention relates to the process for using the bilayer resist to make resist images in a film in the manufacture of integrated circuits.
- the present invention relates to a positive tone, chemically-amplified, radiation-sensitive bilayer resist.
- the bilayer resist comprises (a) a top imaging layer comprising (i) a radiation-sensitive acid generator; (ii) a vinyl polymer or copolymer formed by the polymerization of one or more monomers, including a monomer selected from acrylate, methacrylate, hydroxystyrene (optionally substituted with C 1-6 alkyl), and C 5-20 cyclic olefin monomers (preferably C 7-15 , e.g., norbornene and tetracyclododecane); and (iii) a compound having a silylethoxy acid-cleavable group; and (b) a polymeric organic underlayer.
- the ethoxy portion of the silylethoxy group is optionally substituted with C 1-6 alkyl, phenyl, or benzyl.
- the vinyl polymer may optionally comprises other types of monomers known to those skilled in the art.
- the silicon-containing, acid-cleavable group is bonded to the vinyl polymer.
- the resist is chemically amplified in that the proton produced in the photoreaction of the radiation-sensitive acid generator initiates catalytic cleavage reactions of the acid-cleavable group independent of the radiation, thereby increasing the effective quantum yield to values above 1.
- the silicon-containing, acid-cleavable group consists of silicon atoms, carbon atoms, hydrogen atoms, and one oxygen atom.
- Suitable acid-cleavable silylethoxy groups have the formula R 1 R 2 R 3 Si (CR′ 2 ) 2 O, where each R′ is independently hydrido, C 1-6 alkyl (e.g., methyl), phenyl, or benzyl optionally substituted with C 1-6 alkyl and R 1 , R 2 , and R 3 are each independently hydrido, alkyl preferably lower (C 1-6 ) alkyl or (R 4 ) 3 Si, where each R 4 is independently hydrido or lower alkyl.
- Preferred silicon-containing, acid-cleavable groups are C 1-6 alkyl silylethoxy; mono, bis, tris (C 1-6 alkyl silyl) silylethoxy.
- the bridging alkylene (CR 2 ′) 2 group is important in that it enables nonhydrolytic, solid state, acid-catalyzed cleavable of the acid-cleavable group which is believed to occur through the formation of a beta silyl carbocation as a cleaving group.
- the top imaging layer of the present invention is not crosslinked (uncrosslinked) and has a high silicon content to give enhanced stability against reactive ion etching.
- the top imaging layer is also hydrolytically stable and the top layer composition has enhanced shelf stability.
- the top imaging layer comprises a radiation-sensitive acid generator and an acrylate or methacrylate polymer having an acid-cleavable, silicon-containing group (e.g., silylethoxy) attached to the carbonyl of the acrylate or methacrylate.
- an acid-cleavable, silicon-containing group e.g., silylethoxy
- the silicon-containing acrylate or methacrylate can be used as a homopolymer or can be a copolymer.
- Suitable comonomers include (i) acrylate or methacrylate monomers with lower alkyl ester groups, (ii) acrylic acid or methacrylic acid monomers, (iii) methacrylate or acrylate monomers with other types of acid labile ester groups such as tertiary alkyl esters (t-butyl esters), or (iv) hydroxystyrene.
- the polymer in the top imaging layer can be an alicyclic polymer having an alicyclic backbone (e.g., formed from cyclic olefin monomer) where the silicon-containing, acid-cleavable group (e.g., silylethoxy) is preferably bonded to a carbonyl group attached to the cycloalkyl ring.
- Suitable monomers include functionalized norbornene and tetracyclododecane.
- the top imaging layer comprises a vinyl polymer, an acid generator, and a compound having a silicon-containing, acid-cleavable group.
- Suitable compounds are bisphenol A and steroids (e.g., substituted androstane as disclosed in Allen et al., U.S. Pat. No. 5,580,694, issued Dec. 3, 1996, the disclosure of which is incorporated herein by reference for all purposes).
- Other suitable compounds will be known to those skilled in the art.
- the polymer in the top imaging layer is polyhydroxystyrene where the silicon-containing, acid-cleavable group (e.g., silylethoxy) is bonded directly to the aromatic ring (e.g., as a protected hydroxy substituent).
- the silicon-containing, acid-cleavable group e.g., silylethoxy
- the second component of the top imaging layer is the radiation-sensitive acid generator.
- the radiation-sensitive acid generator Upon exposure to radiation, the radiation-sensitive acid generator generates an acid.
- Suitable acid generators include triflates (e.g., triphenylsulfonium triflate or bis-(t-butyl phenyl) iodonium triflate), pyrogallol (e.g., trimesylate of pyrogallol), onium salts such a triarylsulfonium and diaryl iodonium hexafluoroantimonates, hexafluoroarsenates, trifluoromethane sulfonates and others; iodonium sulfonates and trifluoromethanesulfonate esters of hydroxyimides, alpha-alpha′-bis-sulfonyl diazomethanes, sulfonate esters of nitro-substituted benzyl alcohol
- the two-component top imaging layer generally comprises about 1 to 10 weight % of the acid generator and about 90 to 99 weight % of the polymer.
- the top imaging layer may optionally comprise other minor components such as dissolution inhibitors, coating enhancers, surfactants, bases, and other compounds known to those skilled in the art.
- Suitable organic, polymeric, planarizing underlayers for the resist of the present invention include hard-baked diazonaphthoquinone (DNQ) novolac, polyimides, polyesters, polyacrylates and the like.
- DNQ novolac is the preferred polymer for the underlayer.
- Other crosslinkable polymers known to those skilled in the art can also be used as the underlayer.
- the present invention relates to a process for generating a positive bilayer resist image on a substrate comprising the steps of: (a) coating a substrate with an organic underlayer; (b) coating the organic underlayer with a top layer comprising a radiation-sensitive acid generator and a vinyl polymer having a silicon-containing, acid-cleavable group; (c) imagewise exposing the top layer to radiation; (d) developing the image in the top layer; and (e) transferring the image through the organic underlayer to the substrate.
- the first step of the process of the present invention involves coating the substrate with a layer comprising an organic polymer dissolved in a suitable solvent.
- Suitable substrates are comprised of silicon.
- the surface of the substrate is cleaned by standard procedures before the layer is disposed thereon.
- Suitable solvents for the organic polymer underlayer include propylene glycol methyl ether acetate.
- the layer can be coated on the substrate using art-known techniques such as spin or spray coating, or doctor blading.
- the layer is then heated to an elevated temperature of about 100-250° C. for a short period of time of about 1-30 minutes to drive off solvent and optionally thermally induce crosslinking.
- the dried underlayer layer has a thickness of about 0.5-20 microns, preferably about 1 micron.
- the components of the top imaging layer are dissolved in a suitable solvent such as propylene glycol methyl ether acetate (AMGA) and coated onto the underlayer of organic polymer. It is desired that the imaging layer not admix with the underlayer layer during the coating process.
- the top layer has a thickness of about 0.1 to 0.3 microns.
- the film stack (the top layer and underlayer) is imagewise exposed to radiation, suitably electromagnetic radiation or electron beam radiation, preferably ultraviolet radiation suitably at a wavelength of about 190-365 nm (193/248/254/365/x-ray—hard and soft, e.g., euv 13 nm), preferably 193 or 248 nm.
- radiation sources include mercury, mercury/xenon, and xenon lamps.
- the preferred radiation source is ArF excimer or KrF excimer.
- a sensitizer may be added to the top imaging layer to enhance absorption of the radiation.
- the top layer of the film has a fast photospeed and is fully exposed with less than about 100 mJ/cm 2 of radiation, more preferably less than about 50 mJ/cm 2 .
- the radiation is absorbed by the radiation-sensitive acid generator or sensitizing agent to generate free acid which causes cleavable of the silicon-containing, acid-cleavable group and formation of the corresponding carboxylic acid or phenol.
- the film is again heated to an elevated temperature of about 90-120° C. for a short period of time of about 1 minute.
- the next step involves development of an image in the top layer with a suitable solvent.
- suitable solvents for development of a high contrast, positive image include an aqueous base, preferably an aqueous base without metal ions such as tetramethyl ammonium hydroxide or choline.
- the development results in removal of the exposed areas of the top layer of the film.
- the last step of the process involves transferring of the developed image in the top layer through the underlayer to the substrate by known techniques.
- the image is transferred by etching with reactive ions such as plasma etching and reactive ion etching.
- Suitable plasma tools include electron cyclotron resonance (ECR), helicon, inductively coupled plasma (ICP), and transmission-coupled plasma (TCP) systems.
- ECR electron cyclotron resonance
- ICP inductively coupled plasma
- TCP transmission-coupled plasma
- oxygen-reactive ion etching is utilized to transfer the image through the underlayer.
- Etching techniques are well known in the art and equipment is commercially available to etch films.
- the developed film has high aspect ratio, high etch resistance, enhanced resolution, and straight wall profiles.
- the bilayer resist of the present invention may be used to make an integrated circuit assembly, such as an integrated circuit chip, multichip module, circuit board, or thin film magnetic heads.
- the integrated circuit assembly comprises a circuit formed on a substrate by using the process of the present invention, and then additionally forming a circuit in the developed film on the substrate by art-known techniques.
- circuit patterns can be formed in the exposed areas by coating the substrate with a conductive material such as conductive metals by art-known dry-etching techniques such as evaporation, sputtering, plating, chemical vapor deposition, or laser-induced deposition.
- the surface of the film can be milled to remove any excess conductive material.
- Dielectric materials may also be deposited by similar means during the process of making circuits.
- Inorganic ions such as boron, phosphorous, or arsenic can be implanted in the substrate in the process for making p or n doped circuit transistors. Other means for forming circuits are well known to those skilled in the art.
- Tris(trimethylsilyl)silane (Aldrich), (16.20 grams, 0.065 mole), vinyl acetate (4.50 grams, 0.052 mole), azoisobutyronitrile (2.13 grams, 0.013 mole) and 150 ml toluene were placed in a round bottom flask equipped with a water-cooled condenser and a nitrogen inlet. The contents were evaluated and purged with nitrogen four times with the aid of a Firestone valve. The solution was heated at 90° C. for 4.5 hours. The reaction mixture was concentrated in vacuo. Vacuum distillation gave 17 grams of the product at 100-110° C. at 0.5 mm.
- Lithium aluminum hydride (1.30 grams, 0.033 mole) in 150 ml anhydrous ether was refluxed for 1 hour under nitrogen. The suspension was cooled to room temperature and 2-tris(trimethyl-silyl)ethylacetate (8.76 grams, 0.026 mole) in 50 ml ether was added dropwise. The contents were heated under reflux for 4 hours. Cooled to room temperature and 100 ml ice water was added cautiously. Ether layer was washed with 5% sulfuric acid, followed by deionized water, and finally with brine. The solution was dried over anhydrous magnesium sulfate and the solvent was removed in a rotary evaporator. The white solid obtained was dried under vacuum. Yield: 6.5 grams.
- Methacryloyl chloride (2.50 grams, 0.024 mole) in 25 ml tetrahydro-furan was added dropwise into a solution of 2-tris(trimethylsilyl) silyl ethanol (6.5 grams, 0.022 mole), pyridine (2.0 grams, 0.025 mole) and 25 mg of phenothiazine in 50 ml tetrahydrofuran at room temperature. Stirred at room temperature for two more hours. The solids were filtered off and the solution was washed with 100 ml brine. The solution was then diluted with 100 ml ether and washed with 5% hydrochloric acid, followed by deionized water, and then with brine. It was dried over anhydrous magnesium sulfate and was concentrated in vacuo. Fractional distillation under reduced pressed gave 5 grams of the product at 105-115° C. at 0.5 mm.
- a silicon substrate was coated with 1.1 microns of novolac resist (Shipley 510L) and then soft baked at 95° C. for 60 seconds, followed by 225° C. for 5 min.
- the underlayer was overcoated with 2500 ⁇ of a top imaging layer composition comprising about 95 weight % of copolymer-poly (4-hydroxystyrene-co-2-methacyloxyethyltris (trimethyl) silane and about 5 weight % of a photoacid generator di (tert-butyl) iodonium triflate.
- the films were imagewise exposed at 248 (dose 5-15 mJ/cm 2 ). The film was then baked at 120° C.
- the top layer developed with 0.263 N tetramethyl ammonium hydroxide.
- the images were then transferred through the underlayer by reactive ion etching using a LAM etcher.
- the images formed in the patterned top film showed a vertical wall profile with good process latitude.
- the image transfer through the underlayer maintains the vertical wall profile. There was minimal erosion of the top resist film during the etch step.
Abstract
Description
Claims (81)
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US09/895,624 USRE38282E1 (en) | 1997-03-28 | 2001-06-28 | Process for using bilayer photoresist |
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US08/828,921 US5985524A (en) | 1997-03-28 | 1997-03-28 | Process for using bilayer photoresist |
US09/895,624 USRE38282E1 (en) | 1997-03-28 | 2001-06-28 | Process for using bilayer photoresist |
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US20040086800A1 (en) * | 2002-11-04 | 2004-05-06 | Meagley Robert P. | Photoactive adhesion promoter |
US7501230B2 (en) * | 2002-11-04 | 2009-03-10 | Meagley Robert P | Photoactive adhesion promoter |
US20090076291A1 (en) * | 2002-11-04 | 2009-03-19 | Meagley Robert P | Photoactive adhesion promoter |
US7611828B2 (en) | 2002-11-04 | 2009-11-03 | Meagley Robert P | Photoactive adhesion promoter |
US20060134546A1 (en) * | 2004-12-16 | 2006-06-22 | International Business Machines Corporation | Low refractive index polymers as underlayers for silicon-containing photoresists |
US7326523B2 (en) | 2004-12-16 | 2008-02-05 | International Business Machines Corporation | Low refractive index polymers as underlayers for silicon-containing photoresists |
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