DETAILED ACTION
Claims 1-22 are pending. Claim 1 has been amended.
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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on June 2, 2026 has been entered.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-5 and 7-22 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-23 of U.S. Patent No. 12,619,145. Although the claims at issue are not identical, they are not patentably distinct from each other because both the instant claims and patented claims are directed to iodonium salts having an ethylenically unsaturated carboxylic acid anion and resist compositions thereof. Formula (I) and (IP) of ‘145 when defined as: m1 is 1 to 5, m4 is 2 to 4, at least one R4 is a hydroxy group and at least one R4 is a halogen atom, m2 is 0 to 5, m5 is 0 to 5, when m5 is 1 at least one R5 is a hydroxy group, m7 is 0 to 4, R7 is m8 is 0 or 1, a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, each of the hydrocarbon group may have a substituent, and a —CH2—included in each of the haloalkyl group and the hydrocarbon group may be replaced by —O—, —CO—, —S—or —SO2—, R8 represents a branched alkyl group having 3 or 4 carbon atoms, A1 represents ***—X01-L-01-or ***-L01-X01—, X01 represents-O—or —S—, L01 represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and —CH2—included in each of the hydrocarbon group may be replaced by —O—, —CO—, or —S—, *** represents a bonding site to a benzene ring to which I+ is bonded, A2 represents a hydrocarbon group having 1 to 20 carbon atoms, each of the hydrocarbon group may have a substituent of a halogen or a cyano group, and —CH2—included in each of the hydrocarbon group may be replaced by —O—, —CO—, or —S—, X0 represents a single bond or a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH2—included in the hydrocarbon group may be replaced by —O—, —S—, —CO—or —SO2—, Rbb1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, X10 represents a single bond, *—O—**, *—CO—O—**, *—O—CO—O—** or *-Ax-Ph-Ay-**, Ph represents a phenylene group which may have a substituent, Ax represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, Ay represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, * represents a bonding site to carbon atoms to which Rbb1 is bonded, ** represents a bonding site to L10, and L10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and a —CH2—included in each of the hydrocarbon group may be replaced by —O—, —S—, —SO2—or —CO— encompasses formula (I) of instant claims 1-5 and 7-12 when m1 is 1 or 2, m2 is 0 to 2, m4 is 2, m5 is 2, m7 is 0 to 4, m8 is 0 to 4, R1 and R2 are a hydroxy group, each R4 and R5 are a halogen atom, R7 and R8 are a hydrocarbon group having 3 or 4 carbon atoms or a halogen atom, A1 is ***-X01-L01- where X01 is -O- and L01 is a single bond, A2 is ***-X02-L02- where X02 is -O- and L02 is a single bond, X0 represents a single bond or a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH2—included in the hydrocarbon group may be replaced by —O—, —S—, —CO—or —SO2—, Rbb1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, X10 represents a single bond, *—O—**, *—CO—O—**, *—O—CO—O—** or *-Ax-Ph-Ay-**, Ph represents a phenylene group which may have a substituent, Ax represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, Ay represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, * represents a bonding site to carbon atoms to which Rbb1 is bonded, ** represents a bonding site to L10, and L10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and a —CH2—included in each of the hydrocarbon group may be replaced by —O—, —S—, —SO2—or —CO—. Claims 12-19 of ‘145 encompass instant claims 13-22.
Claims 1-5 and 7-22 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-7, 9-13, 15, and 16 of U.S. Patent No. 11,840,503 in view of claims 1-9 and 11 of U.S. Patent No. 8,614,046. Although the claims at issue are not identical, they are not patentably distinct from each other because both the instant claims and patented claims are directed to iodonium salts having a carboxylic acid anion and resist compositions thereof. Formula (I) of ‘503 when defined as: R1 and R2 each independently represent an iodine atom, R7 and R8 each independently represent a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and —CH2—included in the haloalkyl group and the alkyl group may be replaced by —O—, —CO—, —S— or —SO2—, X1 and X2 represent an oxygen atom, m1 represents an integer of 1 or 2, and when m1 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m2 represents an integer of 0 to 2, and when m2 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m4 represents an integer of 2, a plurality of R4 may be the same or different from each other, m5 represents an integer of 2, a plurality of R5 may be the same or different from each other, m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R7 may be the same or different from each other, m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R8 may be the same or different from each other, in which 1≤m1+m7≤5, 0≤m2+m8≤5, one of R4s represents an iodine atom and the other represents a hydroxy group, one of R5s represents an iodine atom and the other represents a hydroxy group, and AI− represents a carboxylic acid anion encompasses formula (I) of instant claims 1-5 when m1 is 1 or 2, m2 is 0 to 2, m4 is 2, m5 is 2, m7 is 0 to 4, m8 is 0 to 4, R1 and R2 are a hydroxy group, each R4 and R5 are a halogen atom, R7 and R8 are a hydrocarbon group having 3 or 4 carbon atoms or a halogen atom, A1 is ***-X01-L01- where X01 is -O- and L01 is a single bond, and A2 is ***-X02-L02- where X02 is -O- and L02 is a single bond. ‘503 does not teach the carboxylic acid anion of formula (I) of instant claims 1 and 7-12. However, ‘046 teaches a salt of formula (I-Pa) and a polymer comprising a structural unit derived therefrom when defined as: XPa represents a single bond or a C1-C4 alkylene group, RPa represents a single bond, a C4-C36 divalent alicyclic hydrocarbon group or a C6-C36 divalent aromatic hydrocarbon group, and one or more methylene groups in the divalent alicyclic hydrocarbon group can be replaced by --O-- or --CO--, YPa represents a polymerizable group, and ZPa+ represents an organic cation encompasses the instantly claimed anion when X0 is a single bond, an aliphatic hydrocarbon group having 1 to 4 carbon atoms, or an alicyclic hydrocarbon group, L10 is a single bond, and X10 is a single bond or formula (X10-1). It would have been obvious to one of ordinary skill in the art to combine the teachings of ‘503 and ‘046 and arrive at the instant claims through routine experimentation in the art.
Claims 1-22 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 and 10-15 of U.S. Patent No. 11,505,524 in view of claims 1-9 and 11 of U.S. Patent No. 8,614,046. Although the claims at issue are not identical, they are not patentably distinct from each other because both the instant claims and patented claims are directed to iodonium salts having a carboxylic acid anion and resist compositions thereof. Formula (I) of ‘524 when defined as: R1 and R2 each independently represent a hydroxy group, —O—R10, —O—CO—O—R10 or —O-L1-CO—O—R10, L1 represents an alkanediyl group having 1 to 6 carbon atoms, R4, R5, R7 and R8 each independently represent a halogen atom, an alkyl fluoride group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and —CH2— included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO2—, R10 represents an acid-labile group, X1 and X2 each independently represent an oxygen atom or a sulfur atom, m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m2 represents an integer of 0 to 5, and when m2 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m4 represents an integer of 0 to 4, and when m4 is 2 or more, a plurality of R4 may be the same or different from each other, m5 represents an integer of 0 to 4, and when m5 is 2 or more, a plurality of R5 may be the same or different from each other, m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R7 may be the same or different from each other, m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R8 may be the same or different from each other, in which 1≤m1+m7≤5, 0≤m2+m8≤5, and AI− represents a carboxylic acid anion encompasses formula (I) of instant claims 1-6 when R1 and R2 each independently represent a hydroxy group, —O—R10, —O—CO—O—R10 or —O-L1-CO—O—R10, L1 represents an alkanediyl group having 1 to 6 carbon atoms, R4 is a halogen atom or a haloalkyl group having 1 to 12 carbon atoms, and -CH2- included in the haloalkyl group may be replaced by -O-, -CO-, -S-, or -SO2-, R5, R7 and R8 each independently represent a halogen atom, an alkyl fluoride group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and —CH2— included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO2—, R10 represents an acid-labile group, X1 and X2 each independently represent an oxygen atom or a sulfur atom, m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m2 represents an integer of 0 to 5, and when m2 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m4 represents an integer of 1 to 4, and when m4 is 2 or more, a plurality of R4 may be the same or different from each other, m5 represents an integer of 0 to 4, and when m5 is 2 or more, a plurality of R5 may be the same or different from each other, m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R7 may be the same or different from each other, m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R8 may be the same or different from each other, in which 1≤m1+m7≤5, 0≤m2+m8≤5. ‘524 does not teach the carboxylic acid anion of formula (I) of instant claims 1 and 7-12. However, ‘046 teaches a salt of formula (I-Pa) and a polymer comprising a structural unit derived therefrom when defined as: XPa represents a single bond or a C1-C4 alkylene group, RPa represents a single bond, a C4-C36 divalent alicyclic hydrocarbon group or a C6-C36 divalent aromatic hydrocarbon group, and one or more methylene groups in the divalent alicyclic hydrocarbon group can be replaced by --O-- or --CO--, YPa represents a polymerizable group, and ZPa+ represents an organic cation encompasses the instantly claimed anion when X0 is a single bond, an aliphatic hydrocarbon group having 1 to 4 carbon atoms, or an alicyclic hydrocarbon group, L10 is a single bond, and X10 is a single bond or formula (X10-1). It would have been obvious to one of ordinary skill in the art to combine the teachings of ‘524 and ‘046 and arrive at the instant claims through routine experimentation in the art.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1-22 are rejected under 35 U.S.C. 103 as being unpatentable over Komuro et al. (U.S. 2021/0371376) in view of Ichikawa et al. (U.S. 2011/0014566).
Komuro et al. teaches a salt represented by formula (I) [0012] for use as an acid generator in a resist composition [0032] (claim 15) and a specific example include the following cation (I-c-41):
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[page 16] which is equivalent to the cation of formula (I) of instant claims 1-6 and 13 when m1 is 1, m2 is 0, m4 is 2, m5 is 0, m7 is 1, m8 is 01, R1 is -O-R10 where R10 is represented by formula (2a) where Raa1’ is a hydrogen atom, Raa2’ is a hydrocarbon group having 1 carbon atom, and Raa3 is an alkyl group having 2 carbon atoms, R4 is a halogen atom, R7 is a hydrocarbon group having 1 carbon atom, and A1 is ***-X01-L01- where X01 is -O- and L01 is a single bond. Komuro et al. also teaches examples of the organic anion represented by AI− include a sulfonic acid anion, a sulfonylimide anion, a sulfonylmethide anion and a carboxylic acid anion [0124] but does teach the carboxylate anion of formula (I) of claim 1.
However, Ichikawa et al. teaches a salt represented by the formula (I-Pa):
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[0013] wherein XPa represents a single bond or a C1-C4 alkylene group, RPa represents a single bond, a C4-C36 divalent alicyclic hydrocarbon group or a C6-C36 divalent aromatic hydrocarbon group, and one or more methylene groups in the divalent alicyclic hydrocarbon group can be replaced by –O– or –CO–, YPa represents a polymerizable group, and ZPa+ represents an organic cation [0013] and examples of the anion part of the salt represented by the formula (I-Pa) include the followings [0021]:
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,
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,
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,
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, and
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[0021] which are equivalent to the anion of formula (I) of instant claims 1 and 7-12 when X0 is a single bond, an adamantanediyl group, a cycloalkanediyl group having 6 carbon atoms, or chain hydrocarbon group having 1 carbon atom, L10 is a single bond or an alkanediyl group having 1 carbon atom, X10 is a single bond or represented by formula (X10-1), and Rbb1 is a hydrocarbon group having 1 carbon atom. Ichikawa et al. also teaches the polymer of the present invention comprises a structural unit derived from the salt represented by the formula (I-Pa) [0048] and examples of the polymer comprising the structural unit derived from the salt represented by the formula (I-Pa) include a polymer consisting of the structural unit derived from the salt represented by the formula (I-Pa), a polymer consisting of the structural unit derived from the salt represented by the formula (I-Pa) and a structural unit having an acid-labile group in its side chain, a polymer consisting of the structural unit derived from the salt represented by the formula (I-Pa) and a structural unit having no acid-labile group in its side chain, and a polymer consisting of the structural unit derived from the salt represented by the formula (I-Pa), a structural unit having an acid-labile group in its side chain and a structural unit having no acid-labile group in its side chain [0052]. Ichikawa et al. further teaches the photoresist composition of the present invention can contain one or more resins having no structural unit derived from the salt represented by the formula (I-Pa), which is insoluble or poorly soluble in an aqueous alkali solution but becomes soluble in an aqueous alkali solution by the action of an acid [0090] and the photoresist composition can contain two or more kinds of the salt represented by the formula (I-Pa), and can contain two or more kinds of the structural units derived from the salt represented by the formula (I-Pa). The photoresist composition can contain two or more kinds of the resins having no structural units derived from the salt represented by the formula (I-Pa) [0115], see examples 16-28 comprising either a salt of formula (I-Pa) or a resin having a structural unit derived from (I-Pa) [0202] (claims 13-18). Ichikawa et al. also teaches the salt of the present invention and the polymer of the present invention are suitable components of a photoresist composition, and the photoresist composition of the present invention provides a photoresist pattern showing good resolution and good focus margin, and therefore, the photoresist composition of the present invention is suitable for ArF excimer laser lithography, KrF excimer laser lithography, ArF immersion lithography, EUV (extreme ultraviolet) lithography, EUV immersion lithography and EB (electron beam) lithography [0143]. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the teachings of Komuro et al. to include the carboxylic acid anion taught by Ichikawa et al. and arrive at the instant claims through routine experimentation of substituting equally suitable components for the sought invention in order to obtain optimum resolution and focus margin.
With regard to claims 14, 16-20, and 22, Komuro et al. teaches the resist composition comprising of the acid generator salt further comprises of a resin having an acid-labile group [0033] (claims 14 and 16) wherein the resin having an acid-labile group includes at least one of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2):
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and
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wherein La1 and La2 each independently represent —O— or *—O—(CH2)k1—CO—O—, k1 represents an integer of 1 to 7, and * represents a bond to —CO—; Ra4 and Ra5 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom; Ra6 and Ra7 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group obtained by combining these groups; m1 represents an integer of 0 to 14; n1 represents an integer of 0 to 10; and n1′ represents an integer of 0 to 3 [0033-0039] which are equivalent to structural units having an acid-labile group of instant claim 17, specifically formulae (a1-1) and (a1-2) of instant claim 19; and further includes an acid-labile group represented by formula (a2-A):
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[0039] wherein Ra50 represents a hydrogen atom, a halogen atom, 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 alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group, Aa50 represents a single bond or *—Xa51-(Aa52-Xa52)nb— and * represents a bond to carbon atoms to which —Ra50 is bonded; Aa52 represents an alkanediyl group having 1 to 6 carbon atoms; Xa51 and Xa52 each independently represent —O—, —CO—O— or —O—CO—; nb represents 0 or 1; and 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 [0040-0046] which is equivalent to formula (a2-A) of instant claim 20. Komuro et al. also teaches the resist composition as explained above further comprises a method for producing a resist pattern, which comprises of: (1) a step of applying the resist composition according to any one of [12] to [14] on a substrate, (2) a step of drying the applied resist composition to form a composition layer, (3) a step of exposing the composition layer, (4) a step of heating the exposed composition layer, and (5) a step of developing the heated composition layer [0046-0051] (claim 22).
With regard to claim 21, Komuro et al. teaches the salt for use as an acid generator in a resist composition, but does not teach a salt represented by formula (B1).
However, Ichikawa et al. teaches he photoresist composition of the present invention comprises the polymer comprising the structural unit derived from the salt represented by the formula (I-Pa) and an acid generator [0087] Examples of the acid generator include a sulfonic acid generator, and an acid generator having one or more fluorine atoms is preferable. Preferable examples of the acid generator include a salt represented by the formula (I) [0093]:
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[0093] wherein Q1 and Q2, each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, X1 represents a single bond or a C1-C17 saturated hydrocarbon group which can have one or more substituents, and one or more methylene groups in the saturated hydrocarbon group can be replaced by --O-- or --CO--, Y1 represents a C1-C36 aliphatic hydrocarbon group, a C3-C36 alicyclic hydrocarbon group, and the aliphatic hydrocarbon group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group can have one or more substituents, and one or more methylene groups in the aliphatic hydrocarbon group and the alicyclic hydrocarbon group can be replaced by --O-- or --CO--, Z+ represents an organic cation [0093] which is equivalent to formula (B1) of instant claim 21. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the resist composition of Komuro et al. to include the acid generator of Ichikawa et al. and arrive at the instant claims through routine experimentation of combining equally suitable components for the sought invention with a reasonable expectation of success.
Claims 1-22 are rejected under 35 U.S.C. 103 as being unpatentable over Goto et al. (WO2021241086) in view of Ichikawa et al. (U.S. 2011/0014566). U.S. 2023/0148344 is being used as the English translation of ‘086.
Goto et al. teaches a resist composition including a resin (hereinafter also referred to as an “acid-decomposable resin”) having a repeating unit having a group having a polarity that increases through decomposition by the action of an acid (hereinafter also referred to as a “repeating unit having an acid-decomposable group”), in which the resist composition further includes, in addition to the acid-decomposable resin, a compound (hereinafter also referred to as a “specific compound”) having at least one cation (hereinafter also referred to as a “specific cation”) represented by General Formula (1) which will be described later, or the acid-decomposable resin further has, in addition to the repeating unit having an acid-decomposable group, a repeating unit having a cation represented by General Formula (1) which will be described later (hereinafter also referred to as a “specific repeating unit”) [0062] (claims 12-17) wherein the structure of the specific repeating unit is not particularly limited, but a repeating unit represented by General Formula (U) is preferable from the viewpoint that the effect of the present invention is more excellent [0488]:
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[0488] wherein RU1 represents a hydrogen atom or a substituent, LU1 represents a single bond or a divalent linking group. Examples of the divalent linking group include —O—, —OC—, —CO—, —COO—, —OCO—, —S—, —N—, CS—, —SO—, —SO2—, a hydrocarbon group (for example, an alkylene group, a cycloalkylene group, an alkenylene group, and an arylene group) which may have a substituent, and a linking group formed by the linking of a plurality of those groups. Y2− represents an anionic functional group. The definition of the anionic functional group is as described above. Z2+ represents a specific cation. The definition of Z2+ is the same as that of Z2+ in General Formula (3) mentioned above [0489-0492] in which examples of the anionic functional group include —SO3− and a group having —SO3− in a part thereof, —COO− and a group having —COO− in a part thereof, a group having —N−— in a part thereof, and a group having a carbanion (—C−<) in a part thereof [0288] and Z2+'s represents a cation, and at least one of Z2+'s represents the cation represented by General Formula (1) [0327]:
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[0084] wherein a specific example of General Formula (1) includes the following:
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[WO 0208] which is structurally similar to the cation of a salt represented by formula (I) of instant claims 1-4 except m4 is 0 instead of 1 to 4. However, Goto et al. teaches Xd2 is represented by formula (1-1) where Ld2 is a divalent linking group which includes the groups exemplified for Ld1 [0110] in which examples of the divalent linking group represented by Ld1 include —O—, —CO—, —COO—, —S—, —NH—, —CS—, —SO—, —SO2—, a hydrocarbon group (for example, an alkylene group, a cycloalkylene group, an alkenylene group, and an arylene group) which may have a substituent [0101] and examples of the substituent contained in the aromatic hydrocarbon group include a halogen atom [0107] which is equivalent to the cation of a salt represented by formula (I) of instant claims 1-4 and 6 when m1 is 1, R1 is -O-CO-O-R10 where R10 is an acid-labile group represented by formula (1a) where Raa1 and Raa2 are alkyl groups bonded to form an alicyclic hydrocarbon group having 6 carbon atoms, and Raa3 is an aromatic hydrocarbon group having 6 carbon atoms, m4 is 1 where R4 is a halogen atom, m2, m5, and m7 are 0, m8 is 1 where R8 is a hydrocarbon group having 4 carbon atoms, and A1 is ***-X01-L01- where X01 is -S- and L01 is a single bond. Goto et al. does not explicitly teach the carboxylate anion of formula (I) of claim 1.
However, Ichikawa et al. teaches a salt represented by the formula (I-Pa):
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[0013] wherein XPa represents a single bond or a C1-C4 alkylene group, RPa represents a single bond, a C4-C36 divalent alicyclic hydrocarbon group or a C6-C36 divalent aromatic hydrocarbon group, and one or more methylene groups in the divalent alicyclic hydrocarbon group can be replaced by –O– or –CO–, YPa represents a polymerizable group, and ZPa+ represents an organic cation [0013] and examples of the anion part of the salt represented by the formula (I-Pa) include the followings [0021]:
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,
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,
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,
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, and
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[0021]which are equivalent to the anion of formula (I) of instant claims 1 and 7-12 when X0 is a single bond, an adamantanediyl group, a cycloalkanediyl group having 6 carbon atoms, or chain hydrocarbon group having 1 carbon atom, L10 is a single bond or an alkanediyl group having 1 carbon atom, X10 is a single bond or represented by formula (X10-1), and Rbb1 is a hydrocarbon group having 1 carbon atom. Ichikawa et al. also teaches the polymer of the present invention comprises a structural unit derived from the salt represented by the formula (I-Pa) [0048] and examples of the polymer comprising the structural unit derived from the salt represented by the formula (I-Pa) include a polymer consisting of the structural unit derived from the salt represented by the formula (I-Pa), a polymer consisting of the structural unit derived from the salt represented by the formula (I-Pa) and a structural unit having an acid-labile group in its side chain, a polymer consisting of the structural unit derived from the salt represented by the formula (I-Pa) and a structural unit having no acid-labile group in its side chain, and a polymer consisting of the structural unit derived from the salt represented by the formula (I-Pa), a structural unit having an acid-labile group in its side chain and a structural unit having no acid-labile group in its side chain [0052]. Ichikawa et al. further teaches the photoresist composition of the present invention can contain one or more resins having no structural unit derived from the salt represented by the formula (I-Pa), which is insoluble or poorly soluble in an aqueous alkali solution but becomes soluble in an aqueous alkali solution by the action of an acid [0090] and the photoresist composition can contain two or more kinds of the salt represented by the formula (I-Pa), and can contain two or more kinds of the structural units derived from the salt represented by the formula (I-Pa). The photoresist composition can contain two or more kinds of the resins having no structural units derived from the salt represented by the formula (I-Pa) [0115], see examples 16-28 comprising either a salt of formula (I-Pa) or a resin having a structural unit derived from (I-Pa) [0202] (claims 13-18). Ichikawa et al. also teaches the salt of the present invention and the polymer of the present invention are suitable components of a photoresist composition, and the photoresist composition of the present invention provides a photoresist pattern showing good resolution and good focus margin, and therefore, the photoresist composition of the present invention is suitable for ArF excimer laser lithography, KrF excimer laser lithography, ArF immersion lithography, EUV (extreme ultraviolet) lithography, EUV immersion lithography and EB (electron beam) lithography [0143]. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the teachings of Goto et al. to include the specific carboxylic acid anion taught by Ichikawa et al. and arrive at the instant claims through routine experimentation of substituting equally suitable components for the sought invention in order to obtain optimum resolution and focus margin.
With regard to claim 5, Goto et al. teaches regarding General Formula (1) [0327]:
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[0084] where Xd2 represents a group represented by General Formula (1-1) or a leaving group that leaves by the action of an acid [0108]:
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[0108] wherein Ld2 represents a single bond or a divalent linking group [0109] and Rd2 represents a group having a polarity that increases through decomposition by the action of an acid (hereinafter also referred to as an “acid-decomposable group”) [0111] and as the acid-decomposable group, a group represented by each of General Formulae (a-1) to (a-5) is preferable, the group represented by General Formula (a-1) or (a-2) is more preferable [0126]:
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[0141] where * represents a bonding position. Ra2 represents a linear or branched alkyl group which may have a substituent or a cycloalkyl group which may have a substituent [0142] and Ra3 represents a hydrogen atom, a linear or branched alkyl group which may have a substituent, or a cycloalkyl group which may have a substituent [0145] which is equivalent to a salt represented by formula (I) of instant claims 1 and 5 when R1 is -O-R10 when R10 is an acid-labile group represented by formula (2a) of instant claim 6 when Raa1’ is a hydrogen atom, Raa2’ is a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, Xa is an oxygen atom, and Raa3’ is a hydrocarbon group having 1 to 20 carbon atoms.
With regard to claims 19 and 20, Goto et al. teaches the resin (A) includes a repeating unit having a group (hereinafter also referred to as an “acid-decomposable group”) having a polarity that increases through decomposition by the action of an acid. As described above, the resin (A) may further include a repeating unit (specific repeating unit) having a cation represented by General Formula (1) mentioned above (specific cation), in addition to the repeating unit having an acid-decomposable group [0485-0486] and specific examples of the repeating unit having an acid-decomposable group are shown below, but the present invention is not limited thereto. Furthermore, in the formulae, Xa1 represents any one group of H, F, CH3, CF3, or CH2OH, and Rxa and Rxb each independently represent a linear or branched alkyl group having 1 to 5 carbon atoms [0564]:
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[0564] which is equivalent to a structural unit having an acid-labile group represented by formula (a1-0) of instant claim 19 when Ra01 is a hydrogen atom, a halogen atom, or an alkyl group having 1 carbon atom which may have a halogen atom, La01 is a single bond, Ra02 and Ra03 are alkyl groups having 1 carbon atom, and Ra04 is an alicyclic hydrocarbon group having 10 carbon atoms. Goto et al. also teaches the resin (A) may have a repeating unit having an acid group [0611] and as the repeating unit having an acid group, a repeating unit represented by General Formula (I) is also preferable [0630] and he repeating unit represented by General Formula (I) is preferably a repeating unit represented by General Formula (1) [0651]:
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[0651] wherein A represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, or a cyano group. R represents a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group, an aralkyl group, an alkoxy group, an alkylcarbonyloxy group, an alkylsulfonyloxy group, an alkyloxycarbonyl group, or an aryloxycarbonyl group, and in a case where a plurality of R's are present, R's may be the same as or different from each other. In a case where there are a plurality of R's, R's may form a ring in combination with each other. As R, the hydrogen atom is preferable. a represents an integer of 1 to 3. b represents an integer of 0 to (5-a) [0653-0656] which is equivalent to a structural unit represented by formula (a2-A) of instant claim 20 when Ra50 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, or a halogen atom, Aa50 is a single bond, and mb is 0 to 4 where Ra51 is a halogen atom, 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, or an alkylcarbonyloxy group having 2 to 4 carbon atoms.
With regard to claim 21, Goto et al. teaches the resist composition may include another photoacid generator (a compound which does not correspond to the specific compound and generates an acid upon irradiation with actinic rays or radiation) which does not correspond to the specific compound [0780] and examples of such another photoacid generator include the following compound [0804]:
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[0804] which is equivalent to a salt represented by formula (B1) of instant claim 21 when Z+ is an organic cation, Qb1 and Qb2 are fluorine atoms, Lb1 is a divalent saturated hydrocarbon group having 3 carbon atoms in which one -CH2- is replaced by -O- and another -CH2- is replaced by -CO-, and Y is an alicyclic hydrocarbon group having 10 carbon atoms.
With regard to claim 22, Goto et al. teaches the procedure of the pattern forming method using the resist composition is not particularly limited, but preferably has the following steps: Step 1: A step of forming a resist film on a substrate using a resist composition; Step 2: A step of exposing the resist film; Step 3: A step of developing the exposed resist film using a developer to form a pattern [0857-0860] wherein after the application of the resist composition, the substrate may be dried to form a resist film [0868] and it is preferable to perform baking (heating) before performing development after the exposure [0879].
Response to Arguments
Applicant's arguments filed April 29, 2026 have been fully considered but they are not persuasive. Applicant argues regarding the 103 rejection over Komuro in view of Ichikawa, Komuro does not teach the anion such as those described in Ichikawa can be used as the anion of the salt in Komuro. There is no description regarding an anion having a polymerizable group like the anion described in Ichikawa. There would have been no motivation to apply the anion such as those described in Ichikawa to the salt in Komuro. Further, Komuro does not disclose specifically the cation defined in claim 1, i.e. regarding R4. There would have been no motivation to modify the structure of the cation in Komuro so as to meet the requirements of R4 along with R1.
The Examiner respectfully disagrees. Komuro et al. teaches the anion of the salt according to any one of [1] to [5] may be a carboxylic acid anion [0030] and further exemplified in [0250]. Further, Ichikawa et al. teaches photoresist compositions with the salt formula of (I-Pa) [007] gives good line edge roughness [0047] wherein the cation is an organic cation such as an iodonium [0022] and carboxylate anions exemplified in [0021]. Therefore, it would have been obvious at the time of filing to have combined the carboxylate anion of Ichikawa et al. with the iodonium cation of Komuro et al. to result in a resist pattern with satisfactory CD uniformity (CDU) (Komuro et al. [0941]) and good line edge roughness (Ichikawa et al. [0047]). Additionally, Komuro et al. teaches formula (I-c-41) [page 16] which meets the claimed cation requiring at least one R4 representing a halogen atom.
The double patenting rejection over copending application 18/051,050 (now U.S. Patent No. 12, 619,145) is maintained for reasons of record.
Upon further consideration, the double patenting rejection over copending application 18/187,103 in view of Ichikawa has been withdrawn.
Conclusion
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/Anna Malloy/Examiner, Art Unit 1737
/KEITH WALKER/Supervisory Patent Examiner, Art Unit 1735
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