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 .
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 1,3-5,7-11 and 13-14 are rejected under 35 U.S.C. 102(a)(2) as being fully anticipated by Yoshioka et al. WO 2023032797.
Yoshioka et al. WO 2023032797 (machine translation attached) teaches quenchers Q-2, Q-3, Q-6, Q-9 and Q-10
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Polymers P-4 to P-10 includes a photoacid repeating unit and an acid sensitive group. . (table 1 [0444-0446]. Resist R-3 combines polymer P-2, quencher Q-2, photoacid generator P-1 and solvents. Resists R-4, R-5, R-15, R-16,R-19, R-20,R26,R-28 and R-38 are similar and use one of the chromone compounds identified above. The composition of resists R-15, R-16, R-19, R-20 R-26, R-28 and R-38 use polymers having a repeating unit including a photoacid generators MA-1 to MA-3. (reproduced above, see table 2, page 146), the resist solutions are filtered and then coated upon a silicon wafer, dried, exposed using an electron beam, post baked and developed to yield a photoresist pattern and the results are in table 3 (see table 3, page 147 and [0468-0453]). Examples 2-5 and 2-8 coat the resist on a silicon wafer, dry it, expose it using EUV, post baking and then developing the resist to yield a pattern [0465-0467], table 4). These are bounded by formula Q-2,
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X .sup.1 and X .sup.2 each independently represent an oxygen atom or a sulfur atom. R .sup.a1 represents a substituent. n represents an integer of 0 to 3; When n is 2 or more, multiple R .sup.a1 may be the same or different. When n is 2 or more, a plurality of R .sup.a1 may be linked together to form a ring. M .sub.1 .sup.+ is a sulfonium cation or an iodonium cation [0019-0020]. Actinic rays or radiation include infrared light, visible light, ultraviolet light, far ultraviolet light, extreme ultraviolet light, X-rays, and electron beams, preferably 250 nm or less, more preferably 220 nm or less, 1 to 200 nm Particularly preferred are wavelengths of deep UV light, specifically KrF excimer lasers (248 nm), ArF excimer lasers (193 nm), .sub.F2 excimer lasers (157 nm), EUV (13.5 nm), X-rays, and electron beams [0422]. The addition of surfactants is disclosed as improving adhesion and fewer development defects [0396-0398]. Useful photoacid generators can include imide linkages such as BX-10 [0348] and BX-4 [0335] and can be those bounded by formulae 4 or 5 Where .R41 represents a hydrogen atom or a methyl group. .sup.L41 represents a single bond or a divalent linking group. .sup.L42 represents a divalent linking group. .sup.R40 represents a structural site that is decomposed by exposure to actinic rays or radiation to generate an acid in the side chain. In general formula (S-1), R .sup.21 represents a hydrogen atom, an alkyl group, an aryl group, or a halogen atom. X .sup.1 represents a single bond or a divalent linking group. R .sup.c1 to R .sup.c3 each independently represent an alkyl group, an aryl group, or a heteroaryl group. Two of R .sup.c1 to R .sup.c3 may combine to form a ring structure [0207-0232].
With respect to claim 5 and 7, the compositions of the examples inherently can yield either positive tone or negative tone images depending upon the developer (aqueous alkaline or organic solvents) used.
The sulfonium salts used in the examples (P-1) or those attached to the polymer are all strong sulfonic acids (claims 9-10).
The PCT filing date is 8/24/2022 and the priority date is 08/31/2021. These are considered the effective filing dates.
Claims 1,3-5,7 and 9-14 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Hatakeyama et al. JP 2011150103.
Hatakeyama et al. JP 2011150103 (machine translation attached) exemplifies polymers 11 and 12 where the rightmost repeating unit is a chromone and the leftmost repeating unit is acid labile and cleaves to leave a carboxylic acid group bound to the polymer.
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A resist combining polymer 11 with PAG2, amine 1 and PGMEA (solvent) and surfactant FC-4430 is disclosed in table 1 (page 73). A resist combining polymer 12 with PAG2, amine 1 and PGMEA (solvent) and surfactant FC-4430is disclosed in table 1 (page 73). The resist compositions were coated upon a silicon wafer, dried, exposed using an electron beams, post baked and developed in TMAH [0187]. a target pattern is passed through a predetermined mask with a light source selected from high energy rays such as ultraviolet rays, far ultraviolet rays, electron beams, X-rays, excimer lasers, γ rays, synchrotron radiation, and vacuum ultraviolet rays (soft X-rays). Direct exposure is performed. It is preferable to expose so that the exposure amount is about 1 to 200 mJ / cm .sup.2 , preferably 10 to 100 mJ / cm .sup.2 , or 0.1 to 100 μC, and preferably about 0.5 to 50 μC [0099]. The use of repeating unit in the polymer bounded by formulae 5 is disclosed
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Wherein R .sup.20 , R .sup.24 and R .sup.28 are a hydrogen atom or a methyl group, R .sup.21 is a single bond, a phenylene group, —O—R .sup.33 —, or —C (═O) —Y—R .sup.33 —. Y is an oxygen atom or NH, R .sup.33 is a linear, branched or cyclic alkylene group having 1 to 6 carbon atoms, a phenylene group or an alkenylene group, a carbonyl group (—CO—), an ester group (—COO) -), An ether group (-O-) or a hydroxy group, R .sup.22 , R .sup.23 , R .sup.25 , R .sup.26 , R .sup.27 , R .sup.29 , R .sup.30 , R .sup.31 may be the same or different. 1 to 12 linear, branched or cyclic alkyl group, which may contain a carbonyl group, an ester group or an ether group, or an aryl group having 6 to 12 carbon atoms or an aralkyl having 7 to 20 carbon atoms Z .sub.0 represents a single bond, a methylene group, an ethylene group, a phenyl group, or a thiophenyl group. Rene group, fluorinated phenylene group, —O—R .sup.32 —, or —C (═O) —Z .sub.1 —R .sup.32 —, wherein Z .sub.1 is an oxygen atom or NH, and R .sup.32 has 1 to 6 carbon atoms. A linear, branched or cyclic alkylene group, a phenylene group or an alkenylene group, which may contain a carbonyl group, an ester group, an ether group or a hydroxy group, and M .sup.− represents a non-nucleophilic counter ion. 0 ≦ d1 ≦ 0.3, 0 ≦ d2 ≦ 0.3, 0 ≦ d3 ≦ 0.3, 0 ≦ d1 + d2 + d3 ≦ 0.3. Non-nucleophilic counter ions of M .sup.− include halide ions such as chloride ions and bromide ions, triflate, fluoroalkyl sulfonates such as 1,1,1-trifluoroethanesulfonate, nonafluorobutanesulfonate, tosylate, and benzene. Sulfonate, 4-fluorobenzene sulfonate, aryl sulfonate such as 1,2,3,4,5-pentafluorobenzene sulfonate, alkyl sulfonate such as mesylate and butane sulfonate, bis (trifluoromethylsulfonyl) imide, bis (perfluoroethyl) Mention acid such as imide) such as sulfonyl) imide, bis (perfluorobutylsulfonyl) imide, tris (trifluoromethylsulfonyl) methide, tris (perfluoroethylsulfonyl) methide. By binding an acid generator to the polymer main chain, acid diffusion can be reduced, and degradation of resolution due to blurring of acid diffusion can be prevented. Further, the edge roughness (LER, LWR) is improved by uniformly dispersing the acid generator. [0051-0053].
Upon exposure, the acid labile groups is removed, leaving the polymer with both a carboxylic acid moiety and a chromone group and the carboxylic acid anion will associate with the sulfonium salts in the composition, thereby meeting the claims.
With respect to claim 5 and 7, the compositions of the examples inherently can yield either positive tone or negative tone images depending upon the developer (aqueous alkaline or organic solvents) used.
The sulfonium salts used in the examples (P-1) or those attached to the polymer are all strong sulfonic acids (claims 9-10).
Claims 1,3-5 and 7-14 are rejected under 35 U.S.C. 103 as being unpatentable over Yoshioka et al. WO 2023032797.
Yoshioka et al. WO 2023032797 does not exemplify a composition including a surfactant, the use ArF or KrF excimer laser exposures or the full range of photoacid generators disclosed.
With respect to claims 1,3-5 and 7-14, It would have been obvious to modify the cited examples of Yoshioka et al. WO 2023032797 by adding a surfactant to improve the adhesion and reduce development defects as discussed at [0396-00398] with a reasonable expectation of forming a useful resist.
With respect to claims 1,3-5,7-11 and 13-14, it would have been obvious to use other exposure sources disclosed such as excimer lasers disclosed at [0422] in the processes of the examples with a reasonable expectation of forming a useful resist image/pattern.
With respect to claims 1,3-5,7-11 and 13-14, it would have been obvious to modify the composition by using other photoacid generators (separate or polymer bound) embraced by the disclosed cited above with a reasonable expectation of forming a useful resist.
Claims 1,3-5 and 7-14 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. JP 2011150103
Hatakeyama et al. JP 2011150103 does not exemplify the use ArF or KrF excimer laser exposures or the full range of photoacid generators (including pendent photoacid generators) disclosed.
With respect to claims 1,3-5,6,7,9-14, It would have been obvious to one skilled in the art to modify the composition of the examples by replacing the sulfonic acid photoacid generators with other photoacid generators, such as bis (trifluoromethylsulfonyl) imide, bis (perfluorobutylsulfonyl) imide, tris (trifluoromethylsulfonyl) methide or tris (perfluoroethylsulfonyl) methide disclosed at [0051-0053] with a reasonable expectation of forming a useful resist.
With respect to claims 1,3-5,7 and 9-14, it would have been obvious to use other exposure sources disclosed such as the KrF or ArF excimer lasers or soft x rays disclosed at [0099] in the processes of the examples with a reasonable expectation of forming a useful resist image/pattern.
With respect to claims 1,3-5,6,7,9-14, It would have been obvious to one skilled in the art to modify the composition of the examples by replacing the sulfonic acid photoacid generators with polymer bound photoacid generators such as those disclosed with respect to formula 5 with a reasonable expectation of forming a useful resist with reduced acid diffusion and degradation of resolution due to blurring of acid diffusion can be prevented. Further, the edge roughness (LER, LWR) is improved by uniformly dispersing the acid generator. [0051-0053].
Claims 1-5 and 7-14 are rejected under 35 U.S.C. 103 as being unpatentable over Yoshioka et al. WO 2023032797, in view of Hatakeyama et al. 20170184964
Hatakeyama et al. 20170184964 exemplifies resist composition including phenazene salts, useful anions for these salts include carboxylic acids
Resist 1-2 uses quencher 2,
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, polymer 1,
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PAG 1
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water repellant polymers 1
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and an organic solvent. (tables 1, [0158]). Other examiner are similar. The resist are coated on a wafer, dried, exposed using EB, post baked and developed in TMAH [0159]. Useful carboxylic acids are bounded by M-1,
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, where wherein R.sup.18 is hydrogen, or a C.sub.1-C.sub.30 straight, branched or cyclic alkyl group, C.sub.2-C.sub.30 straight, branched or cyclic alkenyl group, C.sub.2-C.sub.30 straight, branched or cyclic alkynyl group, C.sub.6-C.sub.20 aryl group, C.sub.7-C.sub.20 aralkyl group, or C.sub.3-C.sub.20 aromatic or aliphatic heterocycle-containing group, which may contain an ester, ether, sulfide, sulfoxide, carbonate, carbamate, sulfone, halogen, amino, amide, hydroxy, thiol or nitro moiety, with the proviso that R.sup.18 does not contain a group of the formula (A)-3:
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wherein Ar is a C.sub.6-C.sub.16 aromatic group, R.sup.21 and R.sup.22 are each independently hydrogen, hydroxy, alkoxy, C.sub.1-C.sub.6 straight, branched or cyclic alkyl group, or C.sub.6-C.sub.10 aryl group, R.sup.19 is fluorine, or a C.sub.1-C.sub.10 straight, branched or cyclic fluoroalkyl group or fluorophenyl group, which may contain a hydroxy, ether, ester or alkoxy moiety, R.sup.20 is hydrogen, or a C.sub.1-C.sub.10 straight, branched or cyclic alkyl group, C.sub.2-C.sub.10 straight, branched or cyclic alkenyl group, C.sub.2-C.sub.10 straight or branched alkynyl group, or C.sub.6-C.sub.10 aryl group, which may contain a hydroxy, ether, ester or alkoxy moiety. Exemplified carboxylic acids on page 8 include
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(page 11)
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(page 12)
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(page 11) [0053-0057]. In another preferred embodiment, the base polymer is free of an acid labile group and may include a crosslinker. [0032]. In a preferred embodiment, the high-energy radiation is ArF excimer laser radiation of wavelength 193 nm, KrF excimer laser radiation of wavelength 248 nm, EB, or EUV of wavelength 3 to 15 nm [0036]. Repeating units which includes PAGs disclosed include those of formulae d1-d3
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Herein R.sup.20, R.sup.24, and R.sup.28 each are hydrogen or methyl. R.sup.21 is a single bond, phenylene, --O--R.sup.33--, or --C(.dbd.O)--Y--R.sup.33-- wherein Y is oxygen or NH, and R.sup.33 is a straight, branched or cyclic C.sub.1-C.sub.6 alkylene group, alkenylene or phenylene group, which may contain a carbonyl (--CO--), ester (--COO--), ether (--O--) or hydroxyl radical. R.sup.22, R.sup.23, R.sup.25, R.sup.26, R.sup.27, R.sup.29, R.sup.30, and R.sup.31 are each independently a straight, branched or cyclic C.sub.1-C.sub.12 alkyl group which may contain a carbonyl, ester or ether radical, or a C.sub.6-C.sub.12 aryl, C.sub.7-C.sub.20 aralkyl, or thiophenyl group. Z.sup.0 is a single bond, methylene, ethylene, phenylene, fluorophenylene, --O--R.sup.32--, or --C(.dbd.O)--Z.sup.1--R.sup.32-- wherein Z.sup.1 is oxygen or NH, and R.sup.32 is a straight, branched or cyclic C.sub.1-C.sub.6 alkylene group, alkenylene or phenylene group, which may contain a carbonyl, ester, ether or hydroxyl radical. M.sup.- is a non-nucleophilic counter ion. The subscripts d1, d2 and d3 are in the range of 0.ltoreq.d1.ltoreq.0.3, 0.ltoreq.d2.ltoreq.0.3, 0.ltoreq.d3.ltoreq.0.3, and 0.ltoreq.d1+d2+d3.ltoreq.0.3 [0033].
Yoshioka et al. WO 2023032797 does not exemplify sulfonium salts bounded by formula (1) in claim 2.
With respect to claims 1-5 and 7-14, it would have been obvious to one skilled in the art to modify the compositions exemplified or rendered obvious by Yoshioka et al. WO 2023032797 by modifying the quenchers of Yoshioka et al. WO 2023032797 by adding a C2 alkyl linkage between the chromone moiety and the carboxylic acid group in a manner similar to the carboxylic anions
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taught on page 11 of Hatakeyama et al. 20170184964 with a reasonable expectation of forming a useful resist and developed resist pattern based upon the exemplified linkages, the carboxylic anions
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on page 8 which are embraced by the language of formula M-1 of Hatakeyama et al. 20170184964 at [0053-0057].
This meets the embodiment where X2 is a single bond, X1 is a C2 alkyl and R1- to R13 are hydrogen, methyl/alkyl, halogen or a substituent.
With respect to claims 1-5 and 7-14, it would have been obvious to one skilled in the art to modify the compositions exemplified or rendered obvious by Yoshioka et al. WO 2023032797 by modifying the quenchers of Yoshioka et al. WO 2023032797 by adding a ester or ether in combination with a C2 alkyl linkage between the chromone moiety and the carboxylic acid group in a manner similar to the carboxylic anions
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and
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of Hatakeyama et al. 20170184964 with a reasonable expectation of forming a useful resist and developed resist pattern based upon the exemplified linkages, the carboxylic anions
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on page 8 which are embraced by the language of formula M-1 of Hatakeyama et al. 20170184964 at [0053-0057].
This meets the embodiment where X2 is an ether or ester linkage, X1 is a C2 alkyl and R1- to R13 are hydrogen, methyl/alkyl, halogen or a substituent.
Claims 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Yoshioka et al. WO 2023032797 and Katayama et al. 20120288796.
Katayama et al. 20120288796 teaches resist 2-5, which includes polymer 1, photoacid generator PAG-8, salts 2 and solvents. Resists 2-25-2028 are similar, but use polymer 4, PAG 2 salt 1, water repellant polymer (considered a surfactant) and solvents.
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The salts are bounded by formula 5
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Herein R.sup.300 is a C.sub.1-C.sub.25 straight, branched or cyclic alkyl group, C.sub.2-C.sub.25 alkenyl group, C.sub.6-C.sub.25 aryl group or C.sub.7-C.sub.25 aralkyl group, in which a methylene moiety may be substituted by an ether, ester or carbonyl radical, and in which some or all hydrogen atoms may be substituted by at least one radical selected from the group consisting of halogen, hydroxyl, carboxyl, amino, cyano, nitro, and sulfonic acid ester. Exemplified carboxylic acids include
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[0151-0154]. The resist composition of the invention also comprises (B) at least one photoacid generator selected from among an onium salt type photoacid generator capable of generating a sulfonic acid of the general formula (2), an onium salt type photoacid generator capable of generating an imide acid of the general formula (3), and an onium salt type photoacid generator capable of generating a methide acid of the general formula (4), in response to high-energy radiation such as UV, DUV, EUV, EB, x-ray, excimer laser, gamma-ray or synchrotron radiation [0114]. It is acceptable to use a blend of two or more polymers which differ in compositional ratio, molecular weight or dispersity as well as a blend of an inventive polymer and another polymer free of an acid labile group-substituted hydroxyl group [0112]. A surfactant can be added [0162,0166]. The inventors have found that when a resist film of a resist composition comprising a polymer comprising recurring units having a hydroxyl group substituted with an acid labile group, a compound capable of generating a sulfonic acid, imide acid or methide acid upon exposure to high-energy radiation, and a compound capable of generating a carboxylic acid upon exposure to high-energy radiation is exposed and developed in organic solvent, the dissolution contrast during organic solvent development is improved, and a hole pattern having minimized nano edge roughness can be formed via positive/negative reversal [0038]. Repeating units which includes PAGs disclosed include those of formulae d1-d3
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Herein R.sup.20, R.sup.24, and R.sup.28 each are hydrogen or methyl. R.sup.21 is a single bond, phenylene, --O--R.sup.33--, or --C(.dbd.O)--Y--R.sup.33-- wherein Y is oxygen or NH, and R.sup.33 is a straight, branched or cyclic C.sub.1-C.sub.6 alkylene group, alkenylene or phenylene group, which may contain a carbonyl (--CO--), ester (--COO--), ether (--O--) or hydroxyl radical. R.sup.22, R.sup.23, R.sup.25, R.sup.26, R.sup.27, R.sup.29, R.sup.30, and R.sup.31 are each independently a straight, branched or cyclic C.sub.1-C.sub.12 alkyl group which may contain a carbonyl, ester or ether radical, or a C.sub.6-C.sub.12 aryl, C.sub.7-C.sub.20 aralkyl, or thiophenyl group. Z.sup.0 is a single bond, methylene, ethylene, phenylene, fluorophenylene, --O--R.sup.32--, or --C(.dbd.O)--Z.sup.1--R.sup.32-- wherein Z.sup.1 is oxygen or NH, and R.sup.32 is a straight, branched or cyclic C.sub.1-C.sub.6 alkylene group, alkenylene or phenylene group, which may contain a carbonyl, ester, ether or hydroxyl radical. M.sup.- is a non-nucleophilic counter ion. The subscripts d1, d2 and d3 are in the range of 0.ltoreq.d1.ltoreq.0.3, 0.ltoreq.d2.ltoreq.0.3, 0.ltoreq.d3.ltoreq.0.3, and 0.ltoreq.d1+d2+d3.ltoreq.0.3 [0107-0108].
Yoshioka et al. WO 2023032797 does not exemplify sulfonium salts bounded by formula (1) in claim 2.
With respect to claims 1-5 and 7-14, it would have been obvious to one skilled in the art to modify the compositions exemplified or rendered obvious by Yoshioka et al. WO 2023032797 by modifying the quenchers of Yoshioka et al. WO 2023032797 by adding an C1 to C4 alkyl linkage between the chromone moiety and the carboxylic acid group in a manner similar to the pairs
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and
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which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796.
This meets the embodiment where X2 is a single bond, X1 is a C2 alkyl and R1- to R13 are hydrogen, methyl/alkyl, halogen or a substituent.
With respect to claims 1-5 and 7-14, it would have been obvious to one skilled in the art to modify the compositions exemplified or rendered obvious by Yoshioka et al. WO 2023032797 by modifying the quenchers of Yoshioka et al. WO 2023032797 by adding the combination of a ether or ester linkages together with a C1 to C4 alkyl linkage between the chromone moiety and the carboxylic acid group in a manner similar to the pairs
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and
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which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796 which specifically described the replacement of methylene with ether, carbonyl or ester groups.
This meets the embodiment where X2 is a ether or ester linkage, X1 is a C2 alkyl and R1- to R13 are hydrogen, methyl/alkyl, halogen or a substituent.
Katayama et al. 20120288796 does not exemplify the use of a resist including a sulfonium salt of chromone, a polymer binder free of acid labile groups, the full range of photoacids taught or the use of EUV or excimer laser exposure.
With respect to claims 1,3-5,7 and 9-14, It would have been obvious to one skilled in the art to modify the cited examples of Katayama et al. 20120288796 by replacing the carboxylic acids with the chromone carboxylates of Yoshioka et al. WO 2023032797 with a reasonable expectation of forming a useful photoresist and resist pattern.
With respect to claims 1,3-5,7 and 9-14, It would have been obvious to one skilled in the art to modify the cited examples of Katayama et al. 20120288796 by replacing the carboxylic acids with the chromone carboxylates of Yoshioka et al. WO 2023032797 and using EUV, KrF or ArF excimer laser exposure as taught at [0114] of Katayama et al. 20120288796 with a reasonable expectation of forming a useful resist pattern.
With respect to claims 1,3-5,7 and 9-14, It would have been obvious to one skilled in the art to modify the cited examples of Katayama et al. 20120288796 by replacing the carboxylic acids with the chromone carboxylates of Yoshioka et al. WO 2023032797 and replacing at least a portion of the photoacid generator with an imide or methide based upon the teachings at [0038] of Katayama et al. 20120288796 with a reasonable expectation of forming a useful photoresist and resist pattern.
With respect to claims 1,3-5 and 7-14, It would have been obvious to one skilled in the art to modify the cited examples of Katayama et al. 20120288796 by replacing the carboxylic acids with the chromone carboxylates of Yoshioka et al. WO 2023032797 and replacing at least a portion of the photoacid generator with an photoacid repeating unit bounded by formulae d1-d3 of Katayama et al. 20120288796 based upon the teachings at [0107-0108] with a reasonable expectation of forming a useful photoresist and resist pattern.
With respect to claims 1,3-7 and 9-14, It would have been obvious to one skilled in the art to modify the cited examples of Katayama et al. 20120288796 by replacing the carboxylic acids with the chromone carboxylates of Yoshioka et al. WO 2023032797 and adding a polymer which does not have acid labile groups as taught at [0112] of Katayama et al. 20120288796 with a reasonable expectation of forming a useful resist pattern.
With respect to claims 1-5,7 and 9-14, It would have been obvious to one skilled in the art to modify the cited examples of Katayama et al. 20120288796 by replacing the carboxylic acids with chromone carboxylates similar to those of Yoshioka et al. WO 2023032797 , but where an C1 to C4 alkyl linkage is provided between the chromone moiety and the carboxylic acid group in a manner similar to the pairs
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and
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which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796 with a reasonable expectation of forming a useful photoresist and resist pattern.
This meets the embodiment where X2 is a single bond, X1 is a C2 alkyl and R1- to R13 are hydrogen, methyl/alkyl, halogen or a substiuent.
With respect to claims 1-5,7 and 9-14, It would have been obvious to one skilled in the art to modify the cited examples of Katayama et al. 20120288796 by replacing the carboxylic acids with chromone carboxylates similar to those of Yoshioka et al. WO 2023032797 by adding the combination of a ether or ester linkages together with a C1 to C4 alkyl linkage between the chromone moiety and the carboxylic acid group in a manner similar to the pairs
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and
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58
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which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796
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58
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which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796 with a reasonable expectation of forming a useful photoresist and resist pattern.
This meets the embodiment where X2 is a single bond, X1 is a C2 alkyl and R1- to R13 are hydrogen, methyl/alkyl , halogen or a substituent.
The examiner also holds that combination of the above are obvious for the reasons articulated above.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Hatakeyama et al. 20170371177 teaches sulfonium salts based upon carboxylic acids containing iodized benzene/phenyl bounded by formula A
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, where In formula (A), R.sup.1 is hydroxyl, or a C.sub.1-C.sub.6 straight, branched or cyclic alkyl or alkoxy group, C.sub.2-C.sub.6 straight, branched or cyclic acyloxy group, or C.sub.1-C.sub.4 straight, branched or cyclic alkylsulfonyloxy group, in which at least one hydrogen (one or more or even all hydrogen atoms) may be substituted by a halogen atom, or fluorine, chlorine, bromine, amino group, nitro group, cyano group, —NR.sup.5—C(═O)—R.sup.6, or —NR.sup.5—C(═O)—O—R.sup.6, wherein R.sup.5 is hydrogen or a C.sub.1-C.sub.6 straight, branched or cyclic alkyl group, R.sup.6 is a C.sub.1-C.sub.6 straight, branched or cyclic alkyl group or C.sub.2-C.sub.8 straight, branched or cyclic alkenyl group. X is a single bond or a (p+1)-valent C.sub.1-C.sub.20 linking group which may contain an ether, carbonyl, ester, amid; sultone, lactam, carbonate, halogen, hydroxy or carboxy moiety. R.sup.2, R.sup.3 and R.sup.4 are each independently fluorine, chlorine, bromine, iodine, or a C.sub.1-C.sub.12 straight, branched or cyclic alkyl group which may contain an oxo moiety, a C.sub.2-C.sub.12 straight, branched or cyclic alkenyl group which may contain an oxo moiety, C.sub.6-C.sub.20 aryl group, C.sub.7-C.sub.12 aralkyl group or C.sub.7-C.sub.12 aryloxyalkyl group, in which at least one hydrogen (one or more or even all hydrogen atoms) may be substituted by a hydroxy, carboxy, halogen, cyano, amid; nitro, sultone, sulfone or sulfonium salt-containing moiety, or in which an ether, ester, carbonyl, carbonate or sulfonic acid ester moiety may intervene between carbon atoms, or R.sup.2 and R.sup.3 may bond together to form a ring with the sulfur atom to which they are attached, rn is an integer of 1 to 5, n is an integer of 0 to 3, and p is an integer of 1 to 3. Exemplified anions include
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and
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[0053-0058]. The composition can use a base polymer which is free of acid labile groups [0026].
Hatakeyama et al. 20180101094 exemplifies anions
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(page 9)
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(page 10)
Kawabata et al. WO 2014042288 teaches various amine salts of carboxylic acids.
Shimada et al. JP 2001343742 (machine translation attached) teaches iodonium and sulfonium salts of carboxylic acids, useful carboxylic acids include
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(page 38).
Maeda et al. 6528232 teaches sulfonium salts where the sulfonium cation includes a chromone moiety. Exemplified cations include
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which is used in example 13.
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 January 7, 2026