Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
The response of the applicant has been read and given careful consideration. Rejections of the previous action not repeated below are withdrawn. Response to the arguments of the applicant are presented after the first rejection they are directed to.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1 and 3-13 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20200272049.
Hatakeyama et al. 20200272049 teaches quencher 12 and 25, which have the structures
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These are combined with polymer 1, PAG 1, solvents and a water repellent polymer to form resists 12 and 25 in table 1 (page 122)
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Each of the resist compositions in Tables 1 and 2 was spin coated on a silicon wafer having an antireflective coating of 78 nm thick (ARC-29A by Nissan Chemical Industries, Ltd.), and baked on a hotplate at 100° C. for 60 seconds to form a resist film of 300 nm thick. Using an ArF excimer laser immersion lithography scanner NSR—S610C (Nikon Corp., NA 1.00, σ 0.98/0.78, annular illumination), the resist film was exposed to ArF radiation through a 6% halftone phase shift mask bearing a pattern with a hole size of 100 nm and a pitch of 300 nm (on-wafer size). Water was used as the immersion liquid. The resist film was baked (PEB) at the temperature shown in Tables 1 and 2 for 60 seconds and developed in a 2.38 wt % tetramethylammonium hydroxide aqueous solution, yielding a hole pattern with a size of 100 nm and a pitch of 300 nm [0158-0160]. Other quenchers exemplified include
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which are bounded by
formulae A-1 and A-2
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R.sup.1 is a single bond or a C.sub.1-C.sub.30 m-valent hydrocarbon group which may contain at least one moiety selected from among hydroxyl, thiol, ester bond, thioester bond, thionoester bond, ether bond, sulfide bond, halogen, nitro, amino, amide bond, sulfonyl, sulfonate bond, sultone ring, lactam ring, and carbonate, the hydrocarbon group being exclusive of an aromatic group having iodine bonded to the aromatic ring. The m-valent hydrocarbon group may be straight, branched or cyclic and may also be saturated or unsaturated while m is an integer of 1 to 6. Examples thereof include C.sub.1-C.sub.30 alkanes, C.sub.2-C.sub.30 alkenes, C.sub.2-C.sub.30 alkynes, C.sub.3-C.sub.30 cyclic saturated hydrocarbons, C.sub.3-C.sub.30 cyclic unsaturated hydrocarbons, and C.sub.6-C.sub.30 aromatic hydrocarbons, from which the number (m) of hydrogen atoms are eliminated. In formulae (A-1) and (A-2), R.sup.2 and R.sup.3 are each independently a C.sub.1-C.sub.6 alkyl group. R.sup.2 and R.sup.3 may bond together to form a ring with the carbon atom to which they are attached. R.sup.4 and R.sup.6 are each independently hydrogen, a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group. R.sup.5 is a C.sub.1-C.sub.6 alkyl group, C.sub.2-C.sub.6 alkenyl group, C.sub.2-C.sub.6 alkynyl group or C.sub.6-C.sub.12 aryl group. The C.sub.1-C.sub.6 alkyl group may be straight, branched or cyclic, and examples thereof include methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, cyclopentyl, n-hexyl, and cyclohexyl. Examples of the C.sub.1-C.sub.4 straight or branched alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl. Examples of the C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyloxycarbonyl, sec-butyloxycarbonyl, tert-butyloxycarbonyl, n-pentyloxycarbonyl, sec-pentyloxycarbonyl, tert-pentyloxycarbonyl, neopentyloxycarbonyl, n-hexyloxycarbonyl, n-heptyloxycarbonyl, n-octyloxycarbonyl, 2-ethylhexyloxycarbonyl, n-nonyloxycarbonyl, n-decyloxycarbonyl, n-undecyloxycarbonyl, n-dodecyloxycarbonyl, n-tridecyloxycarbonyl, n-pentadecyloxycarbonyl, vinyloxycarbonyl, 1-propenyloxycarbonyl, and 2-propenyloxycarbonyl. The C.sub.2-C.sub.6 alkenyl group may be straight, branched or cyclic and examples thereof include vinyl, 1-propenyl, 2-propenyl, butenyl, hexenyl, and cyclohexenyl. The C.sub.2-C.sub.6 alkynyl group may be straight, branched or cyclic and examples thereof include ethynyl, propynyl, and butynyl. Examples of the C.sub.6-C.sub.12 aryl group include phenyl, tolyl, xylyl, 1-naphthyl and 2-naphthyl. Inter alia, R.sup.2 and R.sup.3 are preferably selected from C.sub.1-C.sub.3 alkyl groups; R.sup.5 is preferably selected from C.sub.1-C.sub.6 alkyl groups, C.sub.2-C.sub.4 alkenyl groups, and C.sub.2-C.sub.4 alkynyl groups; R.sup.4 and R.sup.6 are preferably selected from hydrogen, C.sub.1-C.sub.4 straight or branched alkyl groups, and C.sub.2-C.sub.6 straight or branched alkoxycarbonyl groups. In formulae (A-1) and (A-2), R is a C.sub.2-C.sub.10 alicyclic group to form a ring with the nitrogen atom in the formula. Examples of the ring R include cyclic hydrocarbons such as cyclopropane, cyclopentane, cyclohexane, norbornane and adamantane, in which one carbon atom is replaced by nitrogen atom [0044 -0052]. For example, the resist composition is first applied onto a substrate on which an integrated circuit is to be formed (e.g., Si, SiO.sub.2, SiN, SiON, TiN, WSi, BPSG, SOG, or organic antireflective coating) or a substrate on which a mask circuit is to be formed (e.g., Cr, CrO, CrON, MoSi.sub.2, or SiO.sub.2) by a suitable coating technique such as spin coating, roll coating, flow coating, dipping, spraying or doctor coating. The coating is prebaked on a hot plate at a temperature of 60 to 150° C. for 10 seconds to 30 minutes, preferably at 80 to 120° C. for 30 seconds to 20 minutes. The resulting resist film is generally 0.01 to 2 μm thick. The resist film is then exposed to a desired pattern of high-energy radiation such as UV, deep-UV, EB, EUV, x-ray, soft x-ray, excimer laser light, γ-ray or synchrotron radiation. When UV, deep-UV, EUV, x-ray, soft x-ray, excimer laser light, γ-ray or synchrotron radiation is used as the high-energy radiation, the resist film is exposed thereto through a mask having a desired pattern in a dose of preferably about 1 to 200 mJ/cm.sup.2, more preferably about 10 to 100 mJ/cm.sup.2. When EB is used as the high-energy radiation, the resist film is exposed thereto through a mask having a desired pattern or directly in a dose of preferably about 0.1 to 100 μC/cm.sup.2, more preferably about 0.5 to 50 μC/cm.sup.2. It is appreciated that the inventive resist composition is suited in micropatterning using KrF excimer laser, ArF excimer laser, EB, EUV, x-ray, soft x-ray, γ-ray or synchrotron radiation, especially in micropatterning using EB or EUV. After the exposure, the resist film may be baked (PEB) on a hot plate or in an oven at 30 to 150° C. for 10 seconds to 30 minutes, preferably at 50 to 120° C. for 30 seconds to 20 minutes. After the exposure or PEB, in the case of positive resist, the resist film is developed in a developer in the form of an aqueous base solution for 3 seconds to 3 minutes, preferably 5 seconds to 2 minutes by conventional techniques such as dip, puddle and spray techniques. A typical developer is a 0.1 to 10 wt %, preferably 2 to 5 wt % aqueous solution of tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide (TEAH), tetrapropylammonium hydroxide (TPAH), or tetrabutylammonium hydroxide (TBAH). The resist film in the exposed area is dissolved in the developer whereas the resist film in the unexposed area is not dissolved. In this way, the desired positive pattern is formed on the substrate. Inversely in the case of negative resist, the exposed area of resist film is insolubilized and the unexposed area is dissolved in the developer [0140-0143]. The basis polymer can include
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R.sup.A is each independently hydrogen or methyl. R.sup.11 and R.sup.12 each are an acid labile group. Y.sup.1 is a single bond, phenylene or naphthylene group, or C.sub.1-C.sub.12 linking group containing at least one moiety selected from ester bond and lactone ring. Y.sup.2 is a single bond or ester bond. When the base polymer contains both recurring units (a1) and (a2), R.sup.11 and R.sup.12 may be the same or different [0060-0068].
The photoacid generator can be
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Herein R.sup.A is each independently hydrogen or methyl. Z.sup.1 is a single bond, phenylene group, —O—Z.sup.11—, —C(═O)—O—Z.sup.11— or —C(═O)—NH—Z.sup.11—, wherein Z.sup.11 is a C.sub.1-C.sub.6 alkanediyl group, C.sub.2-C.sub.6 alkenediyl group, or phenylene group, which may contain a carbonyl, ester bond, ether bond or hydroxyl moiety. Z.sup.2 is a single bond, —Z.sup.21—C(═O)—O—, —Z.sup.21—O— or —Z.sup.21—O—C(═O)—, wherein Z.sup.21 is a C.sub.1-C.sub.12 alkanediyl group which may contain a carbonyl moiety, ester bond or ether bond. Z.sup.3 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, —C(═O)—O—Z.sup.31—, or —C(═O)—NH—Z.sup.31—, wherein Z.sup.31 is a C.sub.1-C.sub.6 alkanediyl group, C.sub.2-C.sub.6 alkenediyl group, phenylene group, fluorinated phenylene group, or trifluoromethyl-substituted phenylene group, which may contain a carbonyl moiety, ester bond, ether bond or hydroxyl moiety. R.sup.21 to R.sup.28 are each independently a C.sub.1-C.sub.20 monovalent hydrocarbon group which may contain a heteroatom, any two of R.sup.23, R.sup.24 and R.sup.25 or any two of R.sup.26, R.sup.27 and R.sup.28 may bond together to form a ring with the sulfur atom to which they are attached. “A” is hydrogen or trifluoromethyl. M.sup.− is a non-nucleophilic counter ion [0073-0084]. The resist composition may further comprise an acid generator capable of generating a sulfonic acid, imide acid or methide acid, and/or an organic solvent [0022,0076,0094]. In the resist composition of the invention, a quencher other than the inventive heterocyclic amine compound may be blended. The other quencher is typically selected from conventional basic compounds. Conventional basic compounds include primary, secondary, and tertiary aliphatic amines, mixed amines, aromatic amines, heterocyclic amines, nitrogen-containing compounds with carboxyl group, nitrogen-containing compounds with sulfonyl group, nitrogen-containing compounds with hydroxyl group, nitrogen-containing compounds with hydroxyphenyl group, alcoholic nitrogen-containing compounds, amide derivatives, imide derivatives, and carbamate derivatives. Also included are primary, secondary, and tertiary amine compounds, specifically amine compounds having a hydroxyl group, ether bond, ester bond, lactone ring, cyano group, or sulfonic acid ester bond as described in JP-A 2008-111103, paragraphs [0146]-[0164], and compounds having a carbamate group as described in JP 3790649. Addition of a basic compound may be effective for further suppressing the diffusion rate of acid in the resist film or correcting the pattern profile [0133]. In another preferred embodiment, the base polymer is free of an acid labile group. The resist composition is a chemically amplified negative resist composition [0024]. In the negative resist composition, the crosslinker is preferably added in an amount of 0.1 to 50 parts, more preferably 1 to 40 parts by weight per 100 parts by weight of the base polymer [0132]
Hatakeyama et al. 20200272049 does not exemplify resist compositions which include quenchers bounded by formula 1 and 2 of claim 1
With respect to claims 1,3-6 and 10-11, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with
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based upon the equivalence of the quenchers on pages 4-68 with a reasonable expectation of forming a useful resist composition. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-6 and 10-13, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with quencherssimilar to
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where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68 and the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094] and to use the composition as in the processes of the examples with a reasonable expectation of forming a useful resist pattern. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-6 and 10-13, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with quencher similar to
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where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68 and the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094] and to use the composition as in the processes similar to the examples, but where the ArF exposure is replaced by exposure with i-line, KrF , EUV, or electron beam based upon the equivalence taught at [0140-0143] with a reasonable expectation of forming a useful resist pattern. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-6 and 10-11, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with quencher similar to
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where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68 and the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094] and the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094] with a reasonable expectation of forming a useful resist composition. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-6 and 10-11, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with quenchers similar to
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where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68 and the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094] and to use the composition as in the processes using ArF exposure, i-line, KrF , EUV, or electron beam based upon the equivalence taught at [0140-0143] with a reasonable expectation of forming a useful resist pattern. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-6 and 10-13, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with one similar to
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, where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68,the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094] and to use the composition as in the processes using ArF exposure, i-line, KrF , EUV, or electron beam based upon the equivalence taught at [0140-0143] with a reasonable expectation of forming a useful resist pattern. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-6 and 9-13, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with one similar to
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, but replacing the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group and/or to change the position of attachment of the nitrogen ring in the formula based upon the based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68,the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094], PAG containing repeating units bounded by f1 to f3 are added to the based polymer as disclosure at [0073-0084]
and to use the composition as in the processes using ArF exposure, i-line, KrF , EUV, or electron beam based upon the equivalence taught at [0140-0143] with a reasonable expectation of forming a useful resist pattern. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-6 and 9-11, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with one similar to
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where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68 and the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094] and at least a portion of the PAG used is replaced with a PAG containing repeating unit having the structure f1 to f3 based upon the disclosure at [0022,0076,0094] with a reasonable expectation of forming a useful resist composition. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-6 and 9-13, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with one similar to
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where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68 and the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094] and at least a portion of the PAG used is replaced with a PAG containing repeating unit having the structure f1 to f3 based upon the disclosure at [0022,0076,0094] and to use the composition as in the processes using ArF exposure, i-line, KrF , EUV, or electron beam based upon the equivalence taught at [0140-0143] with a reasonable expectation of forming a useful resist pattern. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-4,7,8 and 10-11, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with one similar to
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where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68 and the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094] and to replace the polymer with a base polymer not having an acid labile group and adding a crosslinker as taught at [0024,0132] with a reasonable expectation of forming a useful resist composition. The water repellent polymer is considered a surfactant.
With respect to claims 1,3-4,7,8 and 10-13, it would have been obvious to one skilled in the art to form the composition of examples 12 or 25 where quencher used is replaced with one similar to
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where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052] and the equivalence of the quenchers on pages 4-68 and the PAG used is replaced with a PAG which generates an imide acid or a methide acid based upon the equivalence at [0022,0076,0094], to replace the polymer with a base polymer not having an acid labile group and adding a crosslinker as taught at [0024,0132] and to use the composition as in the processes using ArF exposure, i-line, KrF , EUV, or electron beam based upon the equivalence taught at [0140-0143] with a reasonable expectation of forming a useful resist pattern. The water repellent polymer is considered a surfactant. The water repellent polymer is considered a surfactant.
The newly applied reference teaches quenchers bounded by the claims where the hydrogen on the nitrogen with a C.sub.1-C.sub.4 straight or branched alkyl group, or C.sub.2-C.sub.12 straight or branched alkoxycarbonyl group based upon the disclosure at [0044-0052]
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 March 2, 2026