DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-14 are pending.
The foreign priority application No. 2022-141871 filed on September 07, 2022 in Japan has been received and it is acknowledged.
Claim Rejections - 35 USC § 103
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 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Komuro et al. (JP 2019-099553A, with machine translation provided by the applicant on December 03, 2025).
With regard to claim 1, Komuro et al. teach a salt of formula (I):
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, wherein Z+ represents an organic cation (par.0005).
The anion portion may be represented by the formulas:
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(par.0018).
A salt comprising an anion selected from anions of formulas (Ia-13) to (Ia-20) and an organic cation Z+ is a salt of formula (I) in claim 1 wherein Q1 and Q2 are fluorine atoms, z=0, X1 is *-CO-O-, L1 is a single bond or a hydrocarbon group with 12 carbon atoms wherein -CH2- may be replaced with -O- and -CO-, Ar is a aromatic group substituted with fluorine atoms and -OH groups, R4 is a hydrocarbon group with 1 carbon atom, R3 is a hydrogen atom, and R5 is an alkyl group with 1 carbon atom.
The group Ar is not substituted with an iodine atom, as required in claim 1.
However, the anions of formulas (Ia-13) to (Ia-20) are anions of the salt in the formula (I), and Komuro et al. teach that in the anion of the salt of formula (I) Ar is an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent (par.0005). The examples of substituents for the aromatic hydrocarbon group Ar include halogen atoms, such as fluorine and iodine atoms (par.0015).
It would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to replace the fluorine atoms with iodine atoms as substituents of the phenylene group in the anions of formulas (Ia-13) to (Ia-20) of Komuro et al., because fluorine and iodine atoms are both taught as substituents for the aromatic group Ar of the anions of the salt of formula (I).
With regard to claim 2, salts comprising an anion selected from anions of formulas (Ia-13) to (Ia-18) wherein the fluorine atoms are replaced by iodine atoms as substituents of the phenylene group are salts of formula (I) wherein Ar is a phenylene group having one or more iodine atoms.
Salts comprising an anion selected from anions of formulas (Ia-19) and (Ia-20) wherein the fluorine atoms are replaced by iodine atoms as substituents of the phenylene group are salts of formula (I) wherein Ar is a phenylene group having one iodine atom and a hydroxy group.
With regard to claim 3, salts comprising an anion selected from anions of formulas (Ia-13) to (Ia-20) wherein the fluorine atoms are replaced by iodine atoms as substituents of the phenylene group are salts of formula (I) wherein X1 is *-CO-O-.
With regard to claim 4, salts comprising an anion selected from anions of formulas (Ia-13) to (Ia-20) wherein the fluorine atoms are replaced by iodine atoms as substituents of the phenylene group are salts of formula (I) wherein R4 is a hydrocarbon group with 1 carbon atom and R3 is a hydrogen atom.
With regard to claim 5, Komuro et al. teach an acid generator comprising the salt of formula (I)(par.0049). Komuro et al. also teach the resin (A1) which is a resin containing a structural unit derived from the salt of formula (I)(par.0100), and this unit functions as acid generator.
With regard to claim 6, Komuro et al. teach the resin (A1) which is a resin containing a structural unit derived from the salt of formula (I)(par.0100).
With regard to claims 7-9, Komuro et al. teach a resist composition comprising an acid generator containing a salt of formula (I) and a polymer having a structural unit having an acid-labile group (polymer (A2)) (composition (a) in par.0101).
Komuro et al. also teach a resist composition comprising the resin (A1) which is a resin containing a structural unit derived from the salt of formula (I)(composition (b) or (c) in par.0101, par.0104). The resin (A1) may further comprise a structural unit having an acid-labile group (A1) in addition to the structural unit derived from the salt of formula (I) (par.0104).
With regard to claim 10, Komuro et al. teach a resist composition comprising resin (A1) which is a resin containing a structural unit derived from the salt of formula (I) and an acid generator comprising the salt of formula (I) (composition (b) in par.0101, par.0104).
With regard to claim 11, Komuro et al. teach that the structural unit having an acid-labile group (A1) may be selected from the group consisting of structural units of formulas (a1-0), (a1-1) and (a1-2):
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, wherein
La01, La1, and La2 each independently represent -O-, or *-O-(CH2)k1-CO-O, k1 represents an integer of 1 to 7, * represents a bond to -CO-;
Ra01, Ra4, and Ra5 each independently hydrogen or methyl;
Ra02, Ra03, and Ra04 independently represent an alkyl group having 1 to 8 carbon atom, an alicyclic group of 3 to 18 carbon atoms, or a group formed by combining these groups;
Ra6 and Ra7 each independently represent an alkyl group having 1 to 8 carbon atoms, an alicyclic group of 3 to 18 carbon atoms, or a group formed by combining these groups;
m1 is an integer from 0 to 14;
n1 is an integer from 0 to 10;
n1’ is an integer from 0 to 3 (par.0112 and par.0114).
With regard to claim 12, Komuro et al. teach that the resin (A1) may also comprise a structural unit having a hydroxy group, such as phenolic hydroxy group (par.0137-0138). The structural unit having a phenolic hydroxy group may be represented by the formula (a2-A):
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, wherein
Ra50 represents hydrogen, halogen, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom;
Ra51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy, or a methacryloyloxy group;
Aa50 is a single bond or *-Xa51-(Aa52-Xa52)nb-, and * represents a bond to a carbon atom to which Ra50 is bonded;
Xa51 and Xa52 each independently represent -O-, -CO-O-, or -O-CO-;
Aa52 each independently represent an alkanediyl group having 1 to 6 carbon atoms;
nb represents 0 or 1;
mb represents an integer of 0 to 4, and when mb is an integer of 2 or more, a plurality of Ra51 may be the same or different from each other (par.0139).
With regard to claim 13, Komuro et al. teach that the resist composition further comprises a salt capable of generating an acid having an acidity lower than that of the acid generated by the acid generator (par.0240).
With regard to claim 14, Komuro et al. teach a method comprising the steps of:
-applying the resist composition onto a substrate;
-drying the applied composition to form a composition layer;
-exposing the composition layer;
-heating the exposed composition layer; and
-developing the composition layer after heating (claim 12, par.0244).
Response to Arguments
Applicant's arguments filed on July 15, 2026 have been fully considered but they are not persuasive.
The examiner would like to note that:
-the objection to the specification is withdrawn after the applicant’s amendment to the specification; and
-the rejection of claim 2 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph is withdrawn after the applicant’s amendment to the claim.
On pages 8-11 of the Remarks the applicant argues that Komuro et al. do not teach a salt of formula (I) wherein Ar is an aromatic hydrocarbon group having 6 to 36 carbon atoms which has an iodine atom and may have other substituents.
However, the examiner would like to note that Komuro et al. (JP 2019-099553A, with machine translation provided by the applicant on December 03, 2025) teach a salt of formula (I):
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, wherein Z+ represents an organic cation (par.0005).
The anion portion may be represented by the formulas:
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(par.0018), and further teaches that a fluorine atom and an iodine atoms are functional equivalents as substituents of the aromatic group Ar (par.0015).
Therefore, one of ordinary skill would have been motivates to replace the fluorine atoms with iodine atoms as substituents of the phenylene group in the anions of formulas (Ia-13) to (Ia-20) of Komuro et al. and obtain the salt of formula (I) in claim 1 of the instant application.
On pages 11 and 12 of the Remarks the applicant argues that the Examples 25-26 using Compositions 1-22 using salts which meet the limitations for Ar provide excellent CD uniformity when compared to Comparative Example 1-3 which uses a salt that does not meet the requirements for Ar. The salt IX-1 used in the comparative examples is the same as salt I-15 of Komuro et al.
The examiner agrees that the compositions in Examples 25-46 give improved CDU in comparison to Comparative Examples 1-3. However, the compositions in Examples 25-46 are not commensurate in scope with claim 1, and are no sufficient to show unexpected superior results of the claimed salt.
The Examples 25-26 use the compositions 1-22 (see Table 3 on page 261), wherein Composition 1 uses a combination of resin A1-6 and the salt I-331, the Composition 2 uses a combination of resin A2-1 and the salt I-331, and the Compositions 3-22 use the resins A1-1 to A-14.
The salt I-331 is a salt of formula (I) in claim 1, wherein R5 is a methyl group, R3 and R4 are hydrogen atoms, Ar is a phenylene group substituted with iodine atoms, L1 is a single bond, X1 is -O-CO-, z=0, Q1 and Q2 are fluorine atoms, and ZI+ is a sulfonium cation.
The resins A1-1, A1-2, A1-6, A1-9, A1-10, A1-13, and A1-14 comprise a repeating unit derived from a salt of formula (I) in claim 1, wherein R5 is a methyl group, R3 and R4 are hydrogen atoms, Ar is a phenylene group substituted with iodine atoms, L1 is a single bond, X1 is -O-CO-, z=0, Q1 and Q2 are fluorine atoms, and ZI+ are sulfonium cations.
The resins A1-3 and A1-7 comprise a repeating unit derived from a salt of formula (I) in claim 1, wherein R5 is a methyl group, R3 and R4 are hydrogen atoms, Ar is a phenylene group substituted with iodine atoms, L1 is a single bond, X1 is -CO-O-, z=1, R1 and R2 are hydrogen atoms, Q1 and Q2 are fluorine atoms, and ZI+ are sulfonium cations.
The resins A1-4, A1-5, and A1-8 comprise a repeating unit derived from a salt of formula (I) in claim 1, wherein R5 is a methyl group, R3 and R4 are hydrogen atoms, Ar is a phenylene group substituted with iodine atoms, L1 is a single bond, X1 is -CO-O-, z=1, R1 is hydrogen atom, R2 is a perfluoroalkyl with 1 carbon atom, Q1 and Q2 are fluorine atoms, and ZI+ are sulfonium cations.
The resin A1-11 comprises a repeating unit derived from a salt of formula (I) in claim 1, wherein R5 is a methyl group, R3 and R4 are hydrogen atoms, Ar is a phenylene group substituted with iodine atoms, L1 is a single bond, X1 is -O-CO-O-, z=1, R1 and R2 are hydrogen atoms, Q1 and Q2 are fluorine atoms, and ZI+ is a sulfonium cation.
The resin A1-12 comprises a repeating unit derived from a salt of formula (I) in claim 1, wherein R5 is a methyl group, R3 and R4 are hydrogen atoms, Ar is a phenylene group substituted with iodine atoms, L1 is a hydrocarbon group with 14 carbon atoms wherein -CH2- are substituted by -O- and -CO-, X1 is -O-CO-, z=0, Q1 and Q2 are fluorine atoms, and ZI+ are sulfonium cations.
However, claim 1 recites a salt of formula (I):
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Par.0009 of the specification of the instant application provides examples for the perfluoroalkyl groups and the alkyl groups as Q1, Q2, R1, and R2.
Par.0010-0011 of the specification of the instant application provide examples for the hydrocarbon group included in L1, and par.0012-0016 provide examples of groups wherein -CH2- included in the hydrocarbon group are replaced by -O-, -S-, -CO-, or -SO2-.
Par.0017 of the specification of the instant application provides examples for the aromatic hydrocarbon group Ar.
Par.0018 of the specification of the instant application provides examples for the hydrocarbon groups R3-R5.
Examples of cations are presented in par.0021-0032 of the specification.
Therefore, the salt of formula (I) in claim 1 may be encompassed by a large number of compounds, and the examples provided in the specification are not sufficient to show unexpected superior results of the claimed salt.
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980) (Claims were directed to a process for removing corrosion at "elevated temperatures" using a certain ion exchange resin (with the exception of claim 8 which recited a temperature in excess of 100°C). Appellant demonstrated unexpected results via comparative tests with the prior art ion exchange resin at 110°C and 130°C. The court affirmed the rejection of claims 1-7 and 9-10 because the term "elevated temperatures" encompassed temperatures as low as 60°C where the prior art ion exchange resin was known to perform well. The rejection of claim 8, directed to a temperature in excess of 100°C, was reversed.). See also In re Peterson, 315 F.3d 1325, 1329-31, 65 USPQ2d 1379, 1382-85 (Fed. Cir. 2003) (data showing improved alloy strength with the addition of 2% rhenium did not evidence unexpected results for the entire claimed range of about 1-3% rhenium); In re Grasselli, 713 F.2d 731, 741, 218 USPQ 769, 777 (Fed. Cir. 1983) (Claims were directed to certain catalysts containing an alkali metal. Evidence presented to rebut an obviousness rejection compared catalysts containing sodium with the prior art. The court held this evidence insufficient to rebut the prima facie case because experiments limited to sodium were not commensurate in scope with the claims.). (MPEP 716.02(d) Unexpected Results Commensurate in Scope With Claimed Invention)
Conclusion
THIS ACTION IS MADE FINAL. 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.
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/ANCA EOFF/Primary Examiner, Art Unit 1722
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