Source: https://patents.google.com/patent/US8715902B2/en
Timestamp: 2019-05-19 15:09:26
Document Index: 390271576

Matched Legal Cases: ['Application No. 60', 'Application No. 2006100798125', 'Application No. 2006', 'Application No. 10', 'Application No. 095115195', 'Application No. 06', 'Application No. 2011', 'Application No. 100116799']

US8715902B2 - Compositions and processes for immersion lithography - Google Patents
US8715902B2
US8715902B2 US12/319,737 US31973709A US8715902B2 US 8715902 B2 US8715902 B2 US 8715902B2 US 31973709 A US31973709 A US 31973709A US 8715902 B2 US8715902 B2 US 8715902B2
US12/319,737
US20090130592A1 (en
2005-05-01 Priority to US67676205P priority Critical
2006-05-01 Priority to US11/414,872 priority patent/US7968268B2/en
2009-01-12 Application filed by Rohm and Haas Electronic Materials LLC filed Critical Rohm and Haas Electronic Materials LLC
2009-01-12 Priority to US12/319,737 priority patent/US8715902B2/en
2009-05-21 Publication of US20090130592A1 publication Critical patent/US20090130592A1/en
2014-05-06 Publication of US8715902B2 publication Critical patent/US8715902B2/en
The present application is a Continuation of U.S. application Ser. No. 11/414,872, filed May 1, 2006, which application claims the benefit of U.S. Provisional Application No. 60/676,762, filed May 1, 2005.
Preferred substantially non-mixable materials for use in photoresists of the invention may be in the form of particles. Such particles may include polymers that are polymerized in the form discrete particles, i.e. as separate and distinct polymer particles. Such polymer particles typically have one or more different characteristics from linear or ladder polymers such as linear or ladder silicon polymers. For example, such polymer particles may have a defined size and a low molecular weight distribution More particularly, in a preferred aspect, a plurality of the polymer particles may be employed in a photoresist of the invention with a mean particle size (dimension) of from about 5 to 3000 angstroms, more preferably from about 5 to 2000 angstroms, still more preferably from about 5 to about 1000 angstroms, yet more preferably from about 10 to about 500 angstroms, even more preferably from 10 to 50 or 200 angstroms. For many applications, particularly preferred particles have a mean particle size of less than about 200 or 100 angstroms.
Preferred non-mixable materials include polymeric materials including hyperbranched polymers. As referred to herein, “hyperbranched polymers” include those materials known as “hyperbranched polymers under the IUPAC nomenclature. See IUPAC. Compendium of Macromolecular Nomenclature (The Purple Book); Metanomski, W. V., Ed.; Blackwell Scientific Publications, Oxford, UK, 1991. Thus, by this nomenclature, a hyperbranched polymer has structural repeating units (or constitutional repeating unit as referred to by (IUPAC) where such structural repeating units each has a covalent connectivity of more than two. Particularly preferred hyperbranched polymers may have minimal (e.g. less than 5, 4, 3, 2 or 1 weight percent) aromatic content, or be completely free of any aromatic content.
1) a phenolic resin that contains acid-labile groups that can provide a is chemically amplified positive resist particularly suitable for imaging at 248 nm. Particularly preferred resins of this class include: i) polymers that contain polymerized units of a vinyl phenol and an alkyl acrylate, where the polymerized alkyl acrylate units can undergo a deblocking reaction in the presence of photoacid. Exemplary all acrylates that can undergo a photoacid-induced deblocking reaction include e.g. t-butyl acrylate, t-butyl methacrylate, methyladamantyl acrylate, methyl adamantyl meacrylate, and other non-cyclic alkyl and alicyclic acrylates that can undergo a photoacid-induced reaction, such as polymers in U.S. Pat. Nos. 6,042,997 and 5,492,793, incorporated herein by reference; ii) polymers that contain polymerized units of a vinyl phenol, an optionally substituted vinyl phenyl (e.g. styrene) that does not contain a hydroxy or carboxy ring substituent, and an alkyl acrylate such as those deblocking groups described with polymers i) above, such as polymers described in U.S. Pat. No. 6,042,997, incorporated herein by reference; and iii) polymers that contain repeat units that comprise an acetal or ketal moiety that will react with photoacid, and optionally aromatic repeat units such as phenyl or phenolic groups; such polymers have been described in U.S. Pat. Nos. 5,929,176 and 6,090,526, as well as blends of i) and/or ii) and/or iii);
3) a resin that is substantially or completely free of phenyl or other aromatic groups that can provide a chemically amplified positive resist particularly suitable for imaging at sub-200 nm wavelengths such as 193 nm. Particularly preferred resins of this class include: i) polymers that contain polymerized units of a non-aromatic cyclic olefin (endocyclic double bond) such as an optionally substituted norbornene, such as polymers described in U.S. Pat. Nos. 5,843,624, and 6,048,664; ii) polymers that contain alkyl acrylate units such as e.g. t-butyl acrylate, t-butyl methacrylate, methyladamantyl acrylate, methyl admantyl methacrylate, and other non-cyclic alkyl and alicyclic acrylates; such polymers have been described in U.S. Pat. No. 6,057,083; European Published Applications EP01008913A1 and EP00930542A1; and U.S. Pat. No. 6,136,501, and iii) polymers that contain polymerized anhydride units, particularly polymerized maleic anhydride and/or itaconic anhydride units, such as disclosed in European Published Application EP01008913A1 and U.S. Pat. No. 6,048,662, as well as blends of i) and/or ii) and/or iii);
For imaging at wavelengths greater than 200 nm, such as 248 nm, phenolic resins are typically preferred. Preferred phenolic resins are poly (vinylphenols) which may be formed by block polymerization, emulsion polymerization or solution polymerization of the corresponding monomers in the presence of a catalyst Vinylphenols useful for the production of polyvinyl phenol resins may be prepared, for example, by hydrolysis of commercially available coumarin or substituted coumarin, followed by decarboxylation of the resulting hydroxy cinnamic acids. Useful vinylphenols may also be prepared by dehydration of the corresponding hydroxy alkyl phenols or by decarboxylation of hydroxy cinnamic acids resulting from the reaction of substituted or nonsubstituted hydroxybenzaldehydes with malonic acid. Preferred polyvinylphenol resins prepared from such vinylphenols have a molecular weight range of from about 2,000 to about 60,000 daltons.
wherein the hydroxyl group be present at either the ortho, meta or para positions throughout the copolymer, and R′ is substituted or unsubstituted alkyl having 1 to about 18 carbon atoms, more typically 1 to about 6 to 8 carbon atoms. Tert-butyl is a generally preferred R′ group. An R′ group may be optionally substituted by e.g. one or more halogen (particularly F, Cl or Br), C1-8alkoxy, C2-8 alkenyl, etc. The units x and y may be regularly alternating in the copolymer, or may be randomly interspersed through the polymer. Such copolymers can be readily formed. For example, for resins of the above formula, vinyl phenols and a substituted or unsubstituted alkyl acrylate such as t-butylacrylate and the like may be condensed under free radical conditions as known in the art. The substituted ester moiety, i.e. R′—O—C(═O)—, moiety of the acrylate units serves as the acid labile groups of the resin and will undergo photoacid induced cleavage upon exposure of a coating layer of a photoresist containing the resin. Preferably the copolymer will have a Mw of from about 8,000 to about 50,000, more preferably about 15,000 to about 30,000 with a molecular weight distribution of about 3 or less, more preferably a molecular weight distribution of about 2 or less. Non-phenolic resins, e.g. a copolymer of an alkyl acrylate such as t-butylacrylate or t-butylmethacrylate and a vinyl alicyclic such as a vinyl norbornanyl or vinyl cyclohexanol compound, also may be used as a resin binder in compositions of the invention. Such copolymers also may be prepared by such free radical polymerization or other known procedures and suitably will have a Mw of from about 8,000 to about 50,000, and a molecular weight distribution of about 3 or less.
Suitable polymers that are substantially or completely free of aromatic groups suitably contain acrylate units such as photoacid-labile acrylate units as may be provided by polymerization of methyladamanatylacrylate, methyladamantylmethacrylate, ethylfenchylacrylate, ethylfenchylmethalate, and the like; fused non-aromatic alicyclic groups such as may be provided by polymerization of a norbornene compound or other alicyclic compound having an endocyclic carbon-carbon double bond; an anhydride such as may be provided by polymerization of maleic anhydride and/or itaconic anhydride; and the like.
A preferred optional additive of resists of the invention is an added base, e.g. a caprolactam, which can enhance resolution of a developed resist relief image. The added base is suitably used in relatively small amounts, e.g. about 1 to 10 percent by weight relative to the PAG, more typically 1 to about 5 weight percent. Other suitable basic additives include ammonium sulfonate salts such as piperidinium p-toluenesulfonate and dicyclohexylammonium p-toluenesulfonate; alkyl amines such as tripropylamine and dodecylamine; aryl amines such as diphenylamine, triphenylamine, aminophenol, 2-(4-aminophenyl)-2-4-hydroxyphenyl)propane, etc.
The photoresists used in accordance with the invention are generally prepared following known procedures. For example, a resist of the invention can be prepared as a coating composition by dissolving the components of the photoresist in a suitable solvent such as, e.g., a glycol ether such as 2-methoxyethyl ether (diglyme), ethylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate; lactates such as ethyl lactate or methyl lactate, with ethyl lactate being preferred; propionates, particularly methyl propionate, ethyl propionate and ethyl ethoxy propionate; a Cellosolve ester such as methyl Cellosolve acetate; an aromatic hydrocarbon such toluene or xylene; or a ketone such as methylethyl ketone, cyclohexanone and 2-heptanone. Typically the solids content of the photoresist varies between 5 and 35 percent by weight of the total weight of the photoresist composition. Blends of such solvents also are suitable.
Following coating of the photoresist onto a surface, it may be dried by heating to remove the solvent until preferably the photoresist coating is tack fee.
As discussed above, photoresist compositions are preferably photoactivated by a short exposure wavelength, particularly a sub-400 nm, sub-300 and sub-200 nm exposure wavelength, with I-line (365 mm), 248 nm and 193 nm being particularly preferred exposure wavelengths as well as EUV and 157 nm.
Following exposure, the film layer of the composition is preferably baked at temperatures ranging from about 70° C. to about 160° C. Thereafter, the film is developed, preferably by treatment with an aqueous based developer such as quaternary ammonium hydroxide solutions such as a tetra-alkyl ammonium hydroxide solution; various anine solutions preferably a 0.26 N tetramethylammonium hydroxide, such as ethyl amine, n-propyl amine, diethyl amine, di-n-propyl amine, triethyl amine, or methyldiethyl amine; alcohol amines such as diethanol amine or triethanol amine; cyclic amines such as pyrrole, pyridine, etc. In general, development is in accordance with procedures recognized in the art.
A reactor vessel is charged with a desired amount of propylene glycol monomethyl ether acetate (PGMEA) and heated to 80° C. with N2 purge. The following monomers (FPA, ECPMA, TMPTA), cross-linker and initiator (t-amyl peroxypivalate) are mixed in PGMEA at 80 to 90 weight % fluid composition in an ice bath. The initiator content is 4% relative to the total amount of monomers and cross-linker. The monomers were used in the following weight amounts: 70 weight % pentafluoracrylate (PFPA), 20 weight % ethyl cyclopentyl methacrylate (ECPMA), and 10 weight % (trimethypropane triacrylate (TMPTA):
EXAMPLES 4-6 Additional Photoresist Leaching Testing
IPSS in Amount of photoacid Contact Angle
photoresists to generator leached of deionized
Example No. total solids into immersion fluid water
EXAMPLES 7-19 Additional Polymer Additives for Photoresists in Accordance with the Invention
A hyperbranched terpolymer was prepared having the following repeat units in the respective molar amounts: x/y/TMPA=70/20/10, wherein repeat units x and y are shown in the immediately below structure.
A linear copolymer was prepared having the following repeat units in the respective molar amounts: y/z=50150, wherein repeat units y and z are shown in the immediately below structure. As can be seen from that structure, the monomer polymerized to provide z-units is 1-cyclohexyl-3-hydroxy-4,4,4-trifluoro-3-(trifluoromethyl)butyl 2-methacrylate.
A linear copolymer was prepared having the following repeat units in the respective molar amounts: y/z=50150, wherein repeat units y and z are shown in the immediately below structure. As can be seen from that structure, the monomers polymerized to provide z-units are 5 and 6-[3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]bicycle[2,2,1]hept-2-yl acrylate.
A linear terpolymer was prepared having the following repeat units in the respective molar amounts: with y/z=50/50, wherein repeat units y, z1 and z2 are shown in the immediately below structure.
EXAMPLES 20-33 Immersion Leaching Analysis
Polymer Leaching,
of mole/cm2,
Example Example Polymer admixed in amount and 60 seconds
No. No. used in specified photoresist Leaching
(compar- addi- without additional polymer added
ative) tional
EXAMPLES 34-45 Water Contact Angle Analysis
The results of these Examples 3445 also show that photoresist compositions of the invention can be prepared to achieve desired water angles, as may be desired by device manufacturers, such as a receding water contact angle of in excess of 70 and/or a sliding water contact angle of less than 20.
of DI water contact angles devel-
Example Example θ θ θ θ oper θ
(a) applying on a substrate a photoresist composition layer comprising:
(i) one or more resins which comprise one or more photoacid-labile groups,
(iii) one or more resins that (a) comprise one or more photoacid-labile groups and (b) are substantially non-mixable with the (i) one or more resins, whereby the (iii) one or more resins migrate toward upper portions of the photoresist composition layer during the step of applying, and the (iii) one or more resins are distinct from the (i) one or more resins; and
(b) immersion exposing the applied photoresist layer to radiation activating for the photoresist composition.
2. The method of claim 1 wherein the (iii) one or more resins are particles.
3. The method of claim 1 wherein the (iii) one or more resins comprise aqueous base-solubilizing groups.
4. The method of claim 1 wherein the (iii) one or more resins comprise Si substitution.
5. The method of claim 1 wherein the (iii) one or more resins comprise photoacid-labile acetal groups.
6. The method of claim 1 wherein the (iii) one or more resins comprise photoacid-labile ester groups.
7. The method of claim 1 wherein the photoresist layer is exposed to radiation having a wavelength of 193 nm activating for the photoresist composition.
8. The method of claim 1 wherein the (iii) one or more resins have a lower surface energy and/or small hydrodynamic volume than the (i) one or more resins.
9. The method of claim 1 wherein the photoresist composition as applied as a spin-coated layer provides a receding water contact angle of in excess of 70 degrees.
10. The method of claim 1 wherein the (iii) one or more resins have a smaller hydrodynamic volume than the (i) one or more resins.
11. The method of claim 1 wherein the (iii) one or more resins are present in the photoresist composition in an amount of 0.1 to 20 weight percent based on total weight of the fluid photoresist composition.
12. The method of claim 1 wherein the (iii) one or more resins are present in the photoresist composition in an amount of up to 1 weight percent based on total solids of the photoresist composition.
13. The method of claim 1 wherein the (iii) one or more resins are present in the photoresist composition in an amount of up to 2 weight percent based on total solids of the photoresist composition.
14. The method of claim 1 wherein the (iii) one or more resins are present in the photoresist composition in an amount of up to 3 weight percent based on total solids of the photoresist composition.
15. The method of claim 1 wherein the photoresist composition provides a decreased amount of acid or organic material detected in immersion fluid associated with the immersion exposure relative to the same photoresist composition that does not comprise the (iii) one or more resins.
16. A method for processing a photoresist composition, comprising:
(iii) one or more resins that (a) are substantially non-mixable with the (i) one or more resins, whereby the (iii) one or more resins migrate toward upper portions of the photoresist composition layer during the step of applying, and the (iii) one or more resins are distinct from the (i) one or more resins; and
17. The method of claim 16 wherein the (iii) one or more resins are particles.
18. The method of claim 16 wherein the (iii) one or more resins are fluorinated.
19. The method of claim 16 wherein the (iii) one or more resins comprise Si substitution.
20. The method of claim 16 wherein the photoresist composition provides a decreased amount of acid or organic material detected in immersion fluid associated with the immersion exposure relative to the same photoresist composition that does not comprise the (iii) one or more resins.
21. The method of claim 16 wherein the photoresist composition as applied as a spin-coated layer provides a receding water contact angle of in excess of 70 degrees.
US12/319,737 2005-05-01 2009-01-12 Compositions and processes for immersion lithography Active US8715902B2 (en)
US67676205P true 2005-05-01 2005-05-01
US11/414,872 US7968268B2 (en) 2005-05-01 2006-05-01 Compositions and processes for immersion lithography
US12/319,737 US8715902B2 (en) 2005-05-01 2009-01-12 Compositions and processes for immersion lithography
US14/270,271 US9563128B2 (en) 2005-05-01 2014-05-05 Compositions and processes for immersion lithography
US11/414,872 Continuation US7968268B2 (en) 2005-05-01 2006-05-01 Compositions and processes for immersion lithography
US14/270,271 Continuation US9563128B2 (en) 2005-05-01 2014-05-05 Compositions and processes for immersion lithography
US20090130592A1 US20090130592A1 (en) 2009-05-21
US8715902B2 true US8715902B2 (en) 2014-05-06
ID=36778362
US11/414,872 Active 2027-02-17 US7968268B2 (en) 2005-05-01 2006-05-01 Compositions and processes for immersion lithography
US12/319,737 Active US8715902B2 (en) 2005-05-01 2009-01-12 Compositions and processes for immersion lithography
US12/319,752 Abandoned US20090123869A1 (en) 2005-05-01 2009-01-12 Compositions and processes for immersion lithography
US13/170,007 Active US9696622B2 (en) 2005-05-01 2011-06-27 Compositions and processes for immersion lithography
US14/270,271 Active US9563128B2 (en) 2005-05-01 2014-05-05 Compositions and processes for immersion lithography
US (5) US7968268B2 (en)
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