Prosecution Insights
Last updated: August 16, 2026
Application No. 18/205,127

RESIST COMPOSITION AND PATTERN FORMING PROCESS

Final Rejection §103
Filed
Jun 02, 2023
Priority
Jun 06, 2022 — JP 2022-091489
Examiner
ANGEBRANNDT, MARTIN J
Art Unit
1737
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Shin-Etsu Chemical Co., Ltd.
OA Round
2 (Final)
55%
Grant Probability
Moderate
3-4
OA Rounds
0m
Est. Remaining
90%
With Interview

Examiner Intelligence

Grants 55% of resolved cases
55%
Career Allowance Rate
759 granted / 1370 resolved
-9.6% vs TC avg
Strong +34% interview lift
Without
With
+34.2%
Interview Lift
resolved cases with interview
Typical timeline
3y 1m
Avg Prosecution
65 currently pending
Career history
1448
Total Applications
across all art units

Statute-Specific Performance

§101
0.4%
-39.6% vs TC avg
§103
44.4%
+4.4% vs TC avg
§102
21.0%
-19.0% vs TC avg
§112
20.5%
-19.5% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1370 resolved cases

Office Action

§103
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 Rejections of the previous action not repeated below are withdrawn based upon the amendment and arguments of the applicant. Responses 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 1,4-7 and 9-14 are rejected under 35 U.S.C. 103 as being unpatentable over Yoshioka et al. WO 2023032797, in view of Hatakeyama et al. 20170184964 Yoshioka et al. WO 2023032797 (machine translation attached) teaches quenchers Q-2, Q-3, Q-6, Q-9 and Q-10 PNG media_image1.png 109 329 media_image1.png Greyscale PNG media_image2.png 126 204 media_image2.png Greyscale PNG media_image3.png 119 381 media_image3.png Greyscale PNG media_image4.png 149 238 media_image4.png Greyscale PNG media_image5.png 136 359 media_image5.png Greyscale 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, PNG media_image6.png 99 181 media_image6.png Greyscale 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]. Moreover, the form of a low-molecular-weight compound and the form incorporated into a part of a polymer (for example, the resin (A) described later) may be used in combination. When the photoacid generator (B) is in the form of being incorporated into a part of the polymer, it may be incorporated into a part of the resin (A), or may be incorporated into a resin different from the resin (A) [0269]. Hatakeyama et al. 20170184964 exemplifies resist composition including phenazene salts, useful anions for these salts include carboxylic acids Resist 1-2 uses quencher 2, PNG media_image7.png 142 317 media_image7.png Greyscale , polymer 1, PNG media_image8.png 157 316 media_image8.png Greyscale PAG 1 PNG media_image9.png 197 328 media_image9.png Greyscale water repellant polymers 1 PNG media_image10.png 202 128 media_image10.png Greyscale 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, PNG media_image11.png 82 250 media_image11.png Greyscale , 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: PNG media_image12.png 77 246 media_image12.png Greyscale 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 PNG media_image13.png 141 230 media_image13.png Greyscale PNG media_image14.png 165 205 media_image14.png Greyscale (page 11) PNG media_image15.png 157 122 media_image15.png Greyscale (page 12) PNG media_image16.png 157 75 media_image16.png Greyscale (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 PNG media_image17.png 145 185 media_image17.png Greyscale PNG media_image18.png 142 218 media_image18.png Greyscale PNG media_image19.png 113 150 media_image19.png Greyscale 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) With respect to claims 1,4,5 and 7-14, it would have been obvious to one skilled in the art to modify the compositions exemplified or rendered obvious and processes using these resists 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 PNG media_image14.png 165 205 media_image14.png Greyscale 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 PNG media_image13.png 141 230 media_image13.png Greyscale 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 1,4-5 and 7-14, it would have been obvious to one skilled in the art to modify the compositions exemplified or rendered obvious and processes using these resists 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 PNG media_image14.png 165 205 media_image14.png Greyscale PNG media_image15.png 157 122 media_image15.png Greyscale and PNG media_image20.png 196 94 media_image20.png Greyscale 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 PNG media_image13.png 141 230 media_image13.png Greyscale 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. With respect to claims 1,4,5 and 7-14, it would have been obvious to one skilled in the art to modify the compositions exemplified or rendered obvious and processes using these resists 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 PNG media_image14.png 165 205 media_image14.png Greyscale 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 PNG media_image13.png 141 230 media_image13.png Greyscale on page 8 which are embraced by the language of formula M-1 of Hatakeyama et al. 20170184964 at [0053-0057] and adding a surfactant as taught at [0396-0398] to improve adhesion and /or adding other photoacid generators based upon the disclosure at [0268] of Yoshioka et al. WO 2023032797 With respect to claims 1,5-7 and 9-14, it would have been obvious to one skilled in the art to modify the compositions exemplified or rendered obvious and processes using these resists 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 PNG media_image14.png 165 205 media_image14.png Greyscale 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 PNG media_image13.png 141 230 media_image13.png Greyscale on page 8 which are embraced by the language of formula M-1 of Hatakeyama et al. 20170184964 at [0053-0057], adding a surfactant as taught at [0396-0398] to improve adhesion and using a polymeric photoacid generator which is separate from the resist polymer based upon the disclosure at [0268] of Yoshioka et al. WO 2023032797 In addition to the basis above, it would have been obvious to one skilled in the art to modify the examples using the composition rendered obvious above by the combination of Yoshioka et al. WO 2023032797 and Hatakeyama et al. 20170184964 using KrF excimer lasers (248 nm), ArF excimer lasers (193 nm), F2 excimer lasers (157 nm) or EUV (13.5 nm) exposure rather than the electron beam exposure used in the examples with a reasonable expectation of forming a useful resist pattern based upon the equivalence at [0422] of Yoshioka et al. WO 2023032797. In the response of 5/21/2025, the applicant argues that one skilled in the art would not be motivated to modify the carboxylate anions of the sulfonium salt quenchers of Yoshioka et al. WO 2023032797 by using the teachings of other the phenazine quenchers of Hatakeyama et al. 20170184964. The examiner disagrees, noting that both are quenchers and Hatakeyama et al. 20170184964 establishes that the linkage between the chromone moiety and a carboxylic acid moiety does not have an effect on the quencher which is a weak acid. Which speaks to the functional equivalence of the quenchers. The applicant is invited to provide a showing regarding the criticality of the linkages between the chromone moiety and the carboxylic acid moiety. Claims 1,4-7 and 9-14 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. PNG media_image21.png 415 326 media_image21.png Greyscale PNG media_image22.png 422 312 media_image22.png Greyscale PNG media_image23.png 215 311 media_image23.png Greyscale PNG media_image24.png 195 312 media_image24.png Greyscale PNG media_image25.png 257 297 media_image25.png Greyscale PNG media_image26.png 185 317 media_image26.png Greyscale The salts are bounded by formula 5 PNG media_image27.png 37 142 media_image27.png Greyscale 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 PNG media_image28.png 122 157 media_image28.png Greyscale PNG media_image29.png 78 152 media_image29.png Greyscale , PNG media_image30.png 187 281 media_image30.png Greyscale PNG media_image31.png 78 140 media_image31.png Greyscale [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 PNG media_image17.png 145 185 media_image17.png Greyscale PNG media_image18.png 142 218 media_image18.png Greyscale PNG media_image19.png 113 150 media_image19.png Greyscale 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 with the recited chromone group bounded by formula (1). With respect to claims 1,4,5,7 and 9-14, 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 PNG media_image28.png 122 157 media_image28.png Greyscale and PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale 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 1,4,5,7 and 9-14,, 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 PNG media_image28.png 122 157 media_image28.png Greyscale and PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale 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. With respect to claims 1,4,5,7 and 9-14,, 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 PNG media_image28.png 122 157 media_image28.png Greyscale and PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale 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.and adding a surfactant as taught at [0396-0398] to improve adhesion and /or adding other photoacid generators based upon the disclosure at [0268] of Yoshioka et al. WO 2023032797 With respect to claims 1,5-7 and 9-14,, 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 PNG media_image28.png 122 157 media_image28.png Greyscale and PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale 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 and adding a surfactant as taught at [0396-0398] to improve adhesion and using a polymeric photoacid generator which is separate from the resist polymer based upon the disclosure at [0268] of Yoshioka et al. WO 2023032797 In addition to the basis above, it would have been obvious to one skilled in the art to modify the examples using the composition rendered obvious above by the combination of Yoshioka et al. WO 2023032797 and Katayama et al. 20120288796 using KrF excimer lasers (248 nm), ArF excimer lasers (193 nm), F2 excimer lasers (157 nm) or EUV (13.5 nm) exposure rather than the electron beam exposure used in the examples with a reasonable expectation of forming a useful resist pattern based upon the equivalence at [0422] of Yoshioka et al. WO 2023032797. 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 1,4,5,7 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 PNG media_image28.png 122 157 media_image28.png Greyscale and PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale 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. With respect to claims 1,4,5,7 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 PNG media_image28.png 122 157 media_image28.png Greyscale and PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796 PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale 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. With respect to claims 1,4,5,7 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 PNG media_image28.png 122 157 media_image28.png Greyscale and PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796 PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796 and adding a surfactant as taught at [0396-0398] to improve adhesion and /or adding other photoacid generators based upon the disclosure at [0268] of Yoshioka et al. WO 2023032797 with a reasonable expectation of forming a useful photoresist and resist pattern. With respect to claims 1,4,5,7 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 PNG media_image28.png 122 157 media_image28.png Greyscale and PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796 PNG media_image29.png 78 152 media_image29.png Greyscale PNG media_image32.png 58 226 media_image32.png Greyscale which are embraced by the language of formula 5 at [0151-0154] of Katayama et al. 20120288796 and adding a surfactant as taught at [0396-0398] to improve adhesion and using a polymeric photoacid generator which is separate from the resist polymer based upon the disclosure at [0268] of Yoshioka et al. WO 2023032797 with a reasonable expectation of forming a useful photoresist and resist pattern. In addition to the basis above, it would have been obvious to one skilled in the art to modify the examples using the composition rendered obvious above by the combination of Yoshioka et al. WO 2023032797 and Katayama et al. 20120288796 using KrF excimer lasers (248 nm), ArF excimer lasers (193 nm), F2 excimer lasers (157 nm) or EUV (13.5 nm) exposure rather than the electron beam exposure used in the examples with a reasonable expectation of forming a useful resist pattern based upon the equivalence at [0422] of Yoshioka et al. WO 2023032797. In the response of 5/21/2025, the applicant argues that one skilled in the art would not be motivated to modify the carboxylate anions of the sulfonium salt quenchers of Yoshioka et al. WO 2023032797 by using the teachings of other the phenazine quenchers of Katayama et al. 20120288796. The examiner disagrees, noting that both are quenchers and Katayama et al. 20120288796 establishes that the linkage between the chromone moiety and a carboxylic acid moiety does not have an effect on the quencher which is a weak acid. Which speaks to the functional equivalence of the quenchers. The applicant is invited to provide a showing regarding the criticality of the linkages between the chromone moiety and the carboxylic acid moiety. The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Hatakeyama et al. 20230393462 teaches similar quenchers having the structure PNG media_image33.png 93 185 media_image33.png Greyscale Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a). A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Martin J Angebranndt whose telephone number is (571)272-1378. The examiner can normally be reached 7-3:30 pm EST. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Ching-Yu (Coris) Fung can be reached at 571-270-5713. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. MARTIN J. ANGEBRANNDT Primary Examiner Art Unit 1737 /MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 June 2, 2026
Read full office action

Prosecution Timeline

Jun 02, 2023
Application Filed
Jan 21, 2026
Non-Final Rejection mailed — §103
May 21, 2026
Response Filed
Jun 05, 2026
Final Rejection mailed — §103 (current)

Precedent Cases

Applications granted by this same examiner with similar technology

Patent 12681378
MASK PROCESS CORRECTION METHODS AND METHODS OF FABRICATING LITHOGRAPHIC MASK USING THE SAME
4y 1m to grant Granted Jul 14, 2026
Patent 12681384
PHOTORESIST COMPOSITION
3y 6m to grant Granted Jul 14, 2026
Patent 12675041
Agglutinant for Pellicles, Pellicle Frame with Agglutinant Layer, Pellicle, Exposure Original Plate with Pellicle, Exposure Method, Method for Producing Semiconductor, and Method for Producing Liquid Crystal Display Board
4y 8m to grant Granted Jul 07, 2026
Patent 12675046
BOTTOM ANTIREFLECTIVE COATING MATERIALS
1y 11m to grant Granted Jul 07, 2026
Patent 12663707
PHASE SHIFT BLANKMASK AND PHOTOMASK FOR EUV LITHOGRAPHY
3y 5m to grant Granted Jun 23, 2026
Study what changed to get past this examiner. Based on 5 most recent grants.

Strategy Recommendation AI-generated — please review before filing

Get a prosecution strategy drawn from examiner precedents, rejection analysis, and claim mapping.
Typically takes 5-10 seconds — AI-generated, attorney review required before filing

Prosecution Projections

3-4
Expected OA Rounds
55%
Grant Probability
90%
With Interview (+34.2%)
3y 1m (~0m remaining)
Median Time to Grant
Moderate
PTA Risk
Based on 1370 resolved cases by this examiner. Grant probability derived from career allowance rate.

Sign in with your work email

Enter your email to receive a magic link. No password needed.

Personal email addresses (Gmail, Yahoo, etc.) are not accepted.

Free tier: 3 strategy analyses per month