Detailed Action
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 06/09/2026 has been entered.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 05/14/2026 is being considered by the examiner.
Response to Amendment
Applicant’s Amendments filed 05/14/2026 have been entered. Claims 1 and 11 have been amended. No new matter appears to have been added with these amendments.
Response to Arguments
Applicant’s Amendments and arguments stemming therefrom have rendered the prior art rejections over Komuro and Nishimura moot, as the amendments to change the scope of the group L10 as claimed renders the scope of the claims outside that of the prior art. As such, all rejections are withdrawn.
After further search and consideration, the examiner makes a new grounds of rejection over prior art under 35 USC 103, and a separate provisional rejection on the grounds of Non-statutory Double Patenting over copending US Application 17977158 as set forth in the body of the action below.
With regards to any future arguments concerning unexpected results to overcome an assertion of obviousness: the examiner respectfully submits that assertions directed to data gleaned from experiments using photoresists must be commensurate with the scope of the claims – the independent claim 1 is directed to a Salt, not a resist composition. Claim 14 is the first claimed recitation of a resist composition in the claims.
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.
Claim(s) 1-22 is/are rejected under 35 U.S.C. 103 as being unpatentable over Komuro et al (US 20210341836 A1, published 11/04/2021) and Ohashi et al (US 20100055608 A1)).
Regarding Claims 1-17, Komuro et al teaches a salt represented by a chemical formula, an acid generator, and a resist composition (Abstract).
The specific salt of Komuro conforms to the formula (1) as described from [0050]-[0267], where the salt is an acid generator, delimited more specifically at [008]-[0028].
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R1-R3 reach represent a hydroxyl group, -O-R10, -O-CO-O-R10, or -O-L1-CO-O-R10 (claim 5)
L1 represents a C1-C6 alkanediyl group
R4-R9 each independently may be a halogen, C1-C6 alkyl fluoride, or C1-C18 hydrocarbon group, where the C1-C18 hydrocarbon group may be substituted and a methylene linkage therein may be replaced with oxy, sulfo, carbonyl, or sulfonyl groups
R10 is an acid labile group
X1-X3 may each be an O or S atom
Subscript m1 is 1-5
Subscript m2 and m3 are 0-5, subscripts m4-m7 are 0-4, subscripts m8-m9 are 0-5
A1- is an organic anion
The above formula reads upon the generally claimed cation of claim 1 for where:
R1-R3 reach represent a hydroxyl group, -O-R10, -O-CO-O-R10, or -O-L1-CO-O-R10
L1 represents a C1-C6 alkanediyl group
R4-R9 each independently may be a halogen, C1-C6 alkyl fluoride, or C1-C18 hydrocarbon group, where the C1-C18 hydrocarbon group may be substituted and a methylene linkage therein may be replaced with oxy, sulfo, carbonyl, or sulfonyl groups
R10 is an acid labile group
A1-A3 may each be an O or S atom
a C1 alkanediyl group that is replaced with -O-, or -S-, meets the limitations of the claim - see reference’s X1-X3
For claims 2-4, A1-A3 may each be X01-L01 or L01-X01 (or a corresponding 02 or 03- variant) where X01-X03 are each -O- or -S- and L01-L03 are each a single bond.
Subscript m1 is 1-5
Subscript m2 and m3 are 0-5, subscripts m4-m7 are 0-4, subscripts m8-m9 are 0-5
Specific examples of the cation are depicted at [0118], some of which are replicated here:
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The above cations have acid labile groups that correspond to acid-cleavable sites at both the ester group and at the phenolic oxygen, meeting the limitations of claim 1 where R1 is -O-L1-CO-O-R10, where L1 is a methylene linkage, and where R10 meets the limitations of claim 6 for where:
Regarding formula (1a)
R10 is a t-butyl group, where Raa1-Raa1- are each C1 alkyl
R10 is a methyl adamantyl group, where Raa3 is a methyl group and Raa2 and Raa1 are an alicyclic group having 10 carbon atoms
Regarding formula (2a)
R10 is a group where Raa1’ is a hydrogen, and Raa2’ and Raa3’ are bonded together to form a heterocyclic group having 6 members where Xa is an O atom
R10 is a group where Raa1’ is a hydrogen, Raa2 is a methyl group, and Raa3’ is an ethyl group, where Xa is an O atom
The resist composition of Komuro comprises an acid generator including the salt of formula (1) and a resin having an acid-labile group, as well as other components such as quenchers and solvents ([0324]) (claim 12,14, and 15).
Two or more acid generators, including the salt of formula (1), may be used in the composition ([0269] – a second acid generator may be referred to as generator (B), and may be an acid generator as described from [0268]-[0322]
Komuro does not teach an anion that meets the claim limitations of the anion delimited by the anion in formula (I). Komuro does teach a resin having an acid monomer derived from a sulfonate anion, but such anion does not meet the claim limitations ([0652]-[0688]).
This limitation is met by Ohashi.
Ohashi discloses a polymerizable anion-containing sulfonium salt and a resist composition comprising a polymer derived from the sulfonium salt (Abstract) (claim 13).
The salt of Ohashi is disclosed from [0067]-[0073] and the polymerized form is discussed from [0074]-[0081] as bounded by Formula 1:
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where:
R1 is H, F, Me, or CF3
R2-R4 are each independently a substituted or unsubstituted straight/cyclic/branched C1-C10 alkyl, alkenyl, or oxoalkyl group or a C6-C18 aryl or alkylaryl or oxoaryl group. Two of the R groups may bond to form a ring with the sulfur atom they are attached to.
A is a divalent C1-C20 organic group
Subscript n is 0 or 1
. Examples of the anion of the salt are provided in [0071]:
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The exemplary anions meet the limitations of claim 1 for where:
Q1 and Q2 are a fluorine atom
Lb1 is a divalent C4 alkyl group where one carbon is trifluoro-substituted and two CH2 groups have been replaced with a CO-O group
Yb1 is a norbornane (C7 ring), adamantane (C10 ring), norbornanelactone (C8 ring with 2x O heteroatoms), or cyclohexane (C6 ring) group (corresponding to an alicyclic hydrocarbon having 3-24 carbon atoms which may have a substituent such as lactone, where the embodiments overlap with the claimed range of carbons)
These groups meet the limitations of claim 7 and 8 for where Yb1 is a norbornanediyl , adamantanediyl, or norbornanelactonediyl or cyclohexanediyl group
L10 is a single bond (Claim 11)
X10 is a carboxyl group *-(CO)-O-**
This group meets the limitations of claims 9 and 10 for where claimed X10 corresponds further formula (X10-1)
Rbb1 is a hydrogen or methyl group
The anion is paired with a sulfonium cation such as a substituted triphenylsulfonium.
The composition of Ohashi further includes a resin, where in [0081] the resin contained in the resist composition of the reference is a resin having a structural unit derived from the salt (I), also described as structural unit (Ib). The resin may also comprise further structural units such as units comprising an acid labile group ([0082]-[0164]) (claim 16 and 17).
The anions of Komuro and Ohashi are both directed to fluorinated sulfonic acid embodiments – a person having ordinary skill in the art would consider it obvious to substitute the cation of Komuro into the salt of Ohashi using Ohashi’s anion to arrive at a new species embodiment with the intent to use it as an acid generator in a similar fashion to the salts of Komuro and Ohashi individually (See MPEP 2144.06). Komuro further ascribes improved Critical Dimension Uniformity (CDU) to resist compositions using the salt as disclosed ([0237]).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date through the use of a mixed salt comprising the taught anion of Ohashi and the taught cation of Komuro to arrive at a salt and resist composition comprising such having improved CDU.
Regarding claims 18 and 19, Komuro and Ohashi disclose the limitations of the claims as discussed above regarding claims 1, 14, and 15.
Komuro and Ohashi however do not disclose experimental embodiments that meet the limitations of the claims 18 and 19 having structural units corresponding to acrylate/methacrylate esters and styrene derivatives.
These limitations are met by Komura’s general disclosure.
Komuro teaches the base resin composition from [0326]-[0708], where the resin comprises an acid labile group-bearing substituent such as those bounded by formulas (a1-0) to (a1-2) in [0356]-[0384]:
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Where, as is also present in the claimed invention’s claim 18 :
La01, La1, and La2 reach represent oxo a linkage defined in [0358]
Ra01, Ra4, and Ra5 represent H, halogen, or a C10C6 alkyl group that may be halogenated
Ra02, Ra03 and Ra40 each independently represent an alkyl group having 1 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
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 formed by combining these groups,
Subscript 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.
Examples of the subunit are disclosed in [0381].
The resin of Komuro also discloses a second subunit may be present, unit (a2-A), described as in [0444]-[0469] including examples:
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Ra50 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom,
Ras51 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 bonding site to carbon atoms to which - Ra50 is bonded,
Aa52 represents an alkanediyl group having 1 to 8 carbon atoms,
Xa51 and Xa52 each independently represent -0-, -CO-0- or -O-CO-,
subscript nb represents 0 or 1,
subscript mb represents an integer of 0 to 4, and when mb is an integer of 2 or more, a plurality of Ra5 may be the same or different from each other
These limitations are verbatim with claimed formula (a2-A) in claim 19.
Komuro ascribes improved resolution to resists when the structural units (a1-0)-(a1-2) are present ( [0355]) and improved resolution when using structural units (a2) such as unit (a2-A) ([0441]). A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date by incorporating the units of Komuro into a resist resin such as that of Komuro and Ohashi in order to improve the resolution of a resultant resist pattern formed from processing.
Regarding claim 20, Komuro and Ohashi teach the limitations of the claim as set forth above regarding claims 1 and 14.
Komuro and Ohashi however do not disclose experimental examples that read upon the claims 1, 14, and 20 for the salt (B1).
This limitation is met by the general disclosure of Komuro, which discloses a salt acid generator (B1) from [0268]-[0322]:
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Qbl and Qb2 each independently represent a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms,
Lb1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, -CH2- included in the divalent saturated hydrocarbon group may be replaced by -0- or -CO-, and a hydrogen atom included in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group,
Y represents a methyl group which may have a substituent, or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH2- included in the alicyclic hydrocarbon group may be replaced by -0-, - S-, -SO2- or -CO-,
Z1+ represents an organic cation
The above limitations read nearly verbatim with claim 20 except where Z+ is Z1+. Further examples of salt compounds corresponding to (B1) are depicted from [0316]-[0321].
Komuro discloses that B1 and the salt (1) (and more, additional acid generators) may be used in combination. A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date by incorporating the acid generator salt (B1) into the resist composition of Komuro and Ohashi to improve the resist composition’s sensitivity.
Regarding claim 21, Komuro and Ohashi teach the limitations of the claim as discussed above regarding claims 1 and 14.
Komuro and Ohashi however do not explicitly teach experimental embodiments meeting the limitations of the claim for a salt generating an acid having an acidity lower than that of an acid generated from the salt (1).
The composition of Komuro teaches a quencher from [0720]-[0726], where the composition’s quencher may be a salt generating an acid having acidity lower than that of an acid generated from the acid generators (B), such as a carboxylic acid such as adamantyl carboxylic acid or acetic acid (see Page 112).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date from the general disclosure of Komuro, incorporating the quencher of Komuro into the composition of Komuro and Ohashi to improve the resolution of a resultant resist pattern formed from the composition.
Regarding claim 22, Komuro and Ohashi teach the limitations of the claim as discussed above regarding claims 1 and 14.
Komuro and Ohashi however do not explicitly teach experimental embodiments meeting the limitations of the claim for a lithographic process using the compositions of claims 1 and 14.
These limitations are met by Komuro, which discloses a lithographic process involving the production of a resist pattern, where the resist composition is applied to a substrate, dried to form a film or composition layer, then exposed to radiation, then heated after exposure, and then developed to produce the pattern ([0730]-[0745]).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date from the general disclosure of Komuro, using the composition of Komuro and Ohashi to arrive at a patterned resist product having high resolution imparted by the composition used to make it.
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, 8-10, 12-15, 18, 19, and 21-22 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1, 5-7, 9-15, and 20 of copending Application No. 17977185 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because
Regarding Instant Claim 1 and Reference claim 1:
Both claims are directed to sulfonium sulfonate salts wherein:
in formula (I),
R4, R', R6, R7, R' and R9 each independently represent a halogen atom, a haloalkyl group having I 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 haloalkyl group and the hydrocarbon group may be replaced by -0-
,Al , A2 and A3 each independently represent a hydrocarbon group having 1 to 20 carbon atoms, the hydrocarbon group may have a substituent, and -CH2 - included in the hydrocarbon group may be replaced by -0-, -CO-, -S- or -SO2-,
ml represents an integer of 1 to 5, and when ml 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,
m3 represents an integer of 0 to 5, and when m3 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,
m6 represents an integer of 0 to 4, and when m6 is 2 or more, a plurality of R6 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 R' may be the same or different from each other,
m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R9 may be the same or different from each other,
the sum of m1 and m7 is at least 1 and less than 5, the sum of m2 and m8 is between 0 and 5, and the sum of m3 and m9 is between 0 and 5
QbI and Qb2 each independently represent a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms,
Lb1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, -CH2 - included in the divalent saturated hydrocarbon group may be replaced by - 0- or -CO-, and a hydrogen atom included in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group,
YbI represents a single bond or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH2 - included in the alicyclic hydrocarbon group may be replaced by -0-, -CO-, -S- or -S02 -,
RbbI 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, *-0-**, *-CO-O-**, *-O-CO-O-** or *-Ax-Ph-Ay-
Ph represents a phenylene group which may have a substituent,
Ax represents one bond species selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond and a carbonic acid ester bond,
Ay represents one bond species selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond and a carbonic acid ester bond,
* and ** represent bonding sites, and * represents a bonding site to carbon atoms to which -Rbbi is bonded, and
L10 represents a single bond
The instant claim further recites R1-R3, where when these groups may independently represent -O-R10, and R10 is an acid-labile group, the scope of the Reference’ Claimed R4-R6 overlaps with these groups when Claimed R4-R6 are each a C1-C12 haloalkyl or C1-C18 hydrocarbon group having an -O- substituent therein as the -O-Alkyl group is acid-labile.
A person having ordinary skill in the art implementing the limitations of the Reference claim 1 where at least one of Claimed R4-R6 is a C1-C12 halo-alkoxy group or a C1-C18 alkoxy group would necessarily arrive at the claimed invention of the Instant claim 1.
Instant Claim 8 and reference claim 5 are verbatim.
Instant claim 9 and reference claim 6 are verbatim.
instant claim 10 and reference claim 7 present the same formula under different labels, where claimed X10-1, X10-5, and X10-6 are represented by reference claim’s X1-1, X1-4 and X1-5.
Instant Claim 12 and reference claim 9 are verbatim.
Instant claim 13 and reference claim 10 are verbatim.
Instant claim 14 and reference claim 11 have overlapping scope where the salt of reference claim 11 is an acid generator.
Instant claim 18 and reference claim 12 are verbatim and present the same formulas
Instant claim 19 and reference claim 13 are verbatim
instant claim 21 and reference claim 14 are verbatim
Instant claim 15 and reference claim 15 are nearly verbatim, covering the same functional scope of the salt corresponding to the formulas of claim 1 and a resin having an acid-labile group.
Instant claim 22 and reference claim 20 are verbatim.
A person having ordinary skill in the art would have found it obvious to arrive at the reference application’s invention from the claimed invention of the Instant Application for the above dependent claims when the claim scope of Instant and Reference Claims 1 overlap as described above.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANDREW PRESTON TRAYWICK whose telephone number is (571)272-2982. The examiner can normally be reached Monday - Friday 8-5.
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/A.P.T./Examiner, Art Unit 1737
/SALLY A MERKLING/SPE, Art Unit 1738
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