DETAILED ACTION
Claims 1 and 4-15 are pending. Claim 1 has been amended and claims 2 and 3 have been canceled.
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 .
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 and 4-15 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (U.S. 2019/0369491).
Hatakeyama et al. teaches a resist composition in Example 29 comprising Polymer 3, PAG 6, Ammonium Salt 5, PGMEA, and DAA [p 130] (claims 6 and 12) wherein Polymer 3 is the following:
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[p 127] which is a chemically amplified positive resist comprising (claims 6 and 8) repeat units having the formula (a1) and (a2) of instant claim 7 when RA is methyl, Y1 is a single bond, and R21 is an acid labile group, and Y2 is an ester bond, and R2 is an acid labile group, and formula (f2) of instant claim 11 when RA is methyl, Z2 is -Z21-C(=O)-O- where Z21 is a C10 saturated hydrocarbylene group, RHF is trifluoromethyl, R33 is a C6 hydrocarbyl group, and R34 and R35 are C6 hydrocarbyl groups having a heteroatom bonded to form a ring; PAG 6 is the following:
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[0201] which is equivalent to an acid generator capable of generating a sulfonic acid of instant claims 1 and 5; and Ammonium Salt 5 is the following:
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[0194] in which the cation is structurally similar to a quencher comprising a salt consisting of a nitrogen-containing cation having a carboxy group whose hydrogen is substituted by a tertiary hydrocarbyl group having an androstane structure represented by formula (1) of instant claim 1 except the ester bond is backwards and the anion is equivalent to a non-nucleophilic counter anion of weak acid sulfonamide anion represented by formula (X)-2 of instant claim 4 when R12 is a C1 hydrocarbyl group and R13 is a C7 hydrocarbyl group containing heteroatoms (C=O and three iodines). However, Hatakeyama et al. also teaches Ammonium Salt 5 is a specific example of formula (A) [0064] in which M+ can be an ammonium cation having the following formula (Ac) [0072]:
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[0072] wherein Ra6 can be hydrogen, Ra7 and Ra8 can be C2 monovalent hydrocarbon groups containing an ether bond bonded together to form a ring, and Ra9 can be a C19-C24 monovalent hydrocarbon group having an ester bond and which may have carboxy which can be a combination of straight and cyclic alkyl [0076-0077] in which the ester bond can be either -COO- or -OCO- and configured as a tertiary hydrocarbyl group as seen in the following cation:
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[p 28], such that when the -OCO-C4H8- group seen in Ammonium Salt 5 is replaced by -COO-*C(CH3)- it is equivalent to formula (1) of instant claim 1 when m is 1, two R1 bond together to form a ring which are C2 aliphatic hydrocarbyl groups containing an ether bond, R2 is a single bond, X1 is a single bond, X2 is a single bond, and R is a group having a formula (2)-1 when R3 is a C1 aliphatic hydrocarbyl group, R4 and R5 are oxo groups, and R7 is methyl. Hatakeyama et al. also teaches the ammonium cation is not limited to those shown [0080] and although some preferred embodiments have been described, many modifications and variations may be made thereto in light of the above teachings. It is therefore to be understood that the invention may be practiced otherwise than as specifically described without departing from the scope of the appended claims [0208]. Hatakeyama et al. further teaches an object of the invention is to provide a resist composition which exhibits a high sensitivity and a reduced LWR or improved CDU, independent of whether it is of positive tone or negative tone [0026]. 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 specific teachings of Hatakeyama et al. to include other ammonium cations such as those described above and arrive at the instant claims through routine experimentation of substituting equally suitable variables for the sought invention in order to achieve optimum sensitivity, LWR, and CDU.
With regard to claims 9 and 10, Hatakeyama et al. teaches the above Polymer 3 which is used for a positive resist composition. Hatakeyama et al. does not teach the polymer is free of an acid labile group, i.e. used for a negative resist composition.
However, Hatakeyama et al. teaches the base polymer may be free of an acid labile group. Typically, the resist composition is a chemically amplified negative resist composition [0035-0036]. 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 specific teachings of Hatakeyama et al. to include other polymers and arrive at the instant claims through routine experimentation of substituting equally suitable components for the sought invention in order to obtain either a positive or negative resist.
With regard to claim 13, Hatakeyama et al. teaches the resist composition may further comprise a surfactant [0038].
With regard to claims 14 and 15, Hatakeyama et al. teaches a silicon substrate was coated with an antireflective coating of 60 nm thick (DUV-62, Nissan Chemical Corp.). Each of the resist compositions in Tables 1 to 3 was spin coated on the substrate and prebaked on a hotplate at 105° C. for 60 seconds to form a resist film of 50 nm thick. The resist film was exposed to electron beam using an EB lithography system ELS-F125 (Elionix Co., Ltd., accelerating voltage 125 kV), then baked (PEB) on a hotplate at the temperature shown in Tables 1 to 3 for 60 seconds, and developed with a 2.38 wt % TMAH aqueous solution for 30 seconds to form a pattern [0203].
Claims 1, 4-8, and 12-15 are rejected under 35 U.S.C. 103 as being unpatentable over Namai et al. (JP2017181697) in view of Ichikawa et al. (JP2012226313). Translations previously provided.
Namai et al. teaches a radiation-sensitive resin composition contains the polymer (A), the acid generator (B), the acid diffusion control agent (C), and the solvent (D) [0011] (claims 1, 6, and 12) wherein the polymer (A) is a polymer having the structural unit (I) [0012] which is a structural unit having an acid-dissociable group. Examples of the structural unit (I) include a structural unit represented by the following formula (2-1), a structural unit represented by the following formula (2-2), and the like [0014] (claim 8):
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[0015] wherein R20 is hydrogen, fluoro, methyl or trifluoromethyl. R21 is a monovalent hydrocarbyl group having 1 to 20 carbon atoms. R22 and R23 each independently represent a monovalent chain-hydrocarbon group having 1 to 10 carbon atoms or a monovalent alicyclic-hydrocarbon group having 3 to 20 carbon atoms, or these groups taken together represent an alicyclic structure having 3 to 20 carbon atoms together with the carbon atom to which these groups are bonded. In the above formula (2-2), R24 is hydrogen or methyl. L1 is a bond, -CCOO - or - CONH-. R25, R26, and R27 are each independently hydrogen, a monovalent hydrocarbyl group of 1 to 20 carbon atoms, or a monovalent oxyhydrocarbyl group of 1 to 20 carbon atoms [0016] which are equivalent to repeat units having formula (a1) or (a2) of instant claim 7 when RA is hydrogen or methyl, Y1 is a single bond, R21 is an acid labile group, Y2 is a single bond or ester bond, and R22 is an acid labile group. Namai et al. also teaches the acid generator (B) may be contained in the radiation-sensitive resin composition in the form of a low-molecular-weight compound as described later (hereinafter, referred to as "acid generating agent (B)" as appropriate), in the form of being incorporated as a part of a polymer, or in both of these forms [0087] and is preferably a compound represented by formula (4) [0091] such as the following formula (B-1):
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[0275] which is equivalent to an acid generator capable of generating a sulfonic acid of instant claims 1 and 5. Namai et al. further teaches the acid diffusion control agent (C) is a compound represented by formula (1-1) or formula (1-2) [0112] in which formula (1-1) is the following:
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[0113] wherein R1, R2 and R3 are each independently hydrogen or a monovalent organic group of 1 to 20 carbon atoms, or two or more of these groups taken together represent a ring structure of 3 to 20 ring atoms. L is an (n + 1) -valent organic group having 1 to 20 carbon atoms. X is -OR4 or -NR5R6. R4 is a monovalent organic group having 1 to 20 carbon atoms. R5 and R6 are each independently hydrogen or a C1-C20 monovalent organic group, or taken together represent a C3-C20 aliphatic heterocyclic structure [0114] and the monovalent anion represented by A - is not particularly limited as long as it is a monovalent anion formed by removing one proton from an acid weaker than the acid generated by the acid generator (B). Examples of the monovalent anion represented by A - include a carboxylate anion, a sulfonate anion, an amide anion, an imide anion, a carbanion, a sulfate anion, and a phosphate anion [0171], specifically formulae (d-1) to (g-1) [0172] such as the following (d-1):
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[0173] which is equivalent to a non-nucleophilic counter anion carboxylate anion of instant claim 1 having the formula (X)-1 of instant claim 4 when R11 is a C3 hydrocarbyl group containing a heteroatom (fluorine). Namai et al. also teaches examples of the monovalent hydrocarbyl group having 1 to 20 carbon atoms represented by R4 include monovalent linear hydrocarbyl groups having 1 to 20 carbon atoms, monovalent cycloaliphatic hydrocarbyl groups having 3 to 20 carbon atoms, and monovalent aromatic hydrocarbyl groups having 6 to 20 carbon atoms [0157] and examples of R4 include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl; monocyclic cycloalkenyl groups such as cyclobutenyl, cyclopentenyl, and cyclohexenyl; polycyclic cycloalkyl groups such as norbornyl, adamantyl, tricyclodecyl, and tetracyclododecyl; and polycyclic cycloalkenyl groups such as norbornenyl, tricyclodecenyl, and tetracyclododecenyl [0159]. Namai et al. does not teach an androstane structure as the polycyclic cycloalkyl group R4.
However, Ichikawa et al. teaches a resist composition comprising a salt (X) represented by formula (I) [abstract]:
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[0018] wherein L1 is an alkanediyl group having 1 to 12 carbon atoms, methylene groups constituting the alkanediyl group may be replaced by oxygen atoms or carbonyl groups, and W is formula (W-I):
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[0018] wherein n is an integer of 0 to 6. R1 represents a monovalent aliphatic hydrocarbyl group of 1 to 12 carbon atoms or a monovalent aromatic hydrocarbyl group of 6 to 12 carbon atoms, and a methylene group constituting the monovalent aliphatic hydrocarbyl group may be replaced by an oxygen or carbonyl moiety. M is an integer of 1 to 5 [0018], e.g. n can be 3 where R1 is a monovalent aliphatic hydrocarbyl group of 1 carbon atom, and m is 2. When R4 of Namai’s formula (1-1) is substituted with Ichikawa’s formula (W-I) it is equivalent to a quencher comprising a salt consisting of a nitrogen-containing cation having a carboxy group whose hydrogen is substituted by a tertiary hydrocarbyl group having an androstane structure represented by formula (1) of instant claim 1 when m is 1, two R1 bond together to form a ring which are C2 aliphatic hydrocarbyl groups containing an ether bond, R2 is a single bond, X1 is a single bond, X2 is a single bond, and R is a group having formula (2)-1 when R3 is a C1 aliphatic hydrocarbyl group, R4 and R5 are hydroxy, and R7 is methyl. Ichikawa et al. also teaches when the resist composition of the present invention is used, a resist pattern having excellent CD uniformity (CDU) can be produced [0007]. 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 Namai et al. to include other known polycyclic rings such as those taught by Ichikawa et al. and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention in order to achieve optimum CDU.
With regard to claim 13, Namai et al. teaches the radiation-sensitive resin composition may contain other optional components in addition to the components (A) to (E). Examples of the other optional components include a surfactant, an alicyclic skeleton-containing compound, and a sensitizer. These other optional components may be used alone or in combination of two or more kinds thereof [0241].
With regard to claims 14 and 15, Namai et al. teaches the method for forming a resist pattern includes a step of forming a resist film, a step of exposing the resist film, and a step of developing the exposed resist film [0248] wherein the resist film formed in the resist film forming step is irradiated with radiation through a photomask or the like (in some cases, through a liquid immersion medium such as water) to be exposed. Examples of the radiation include electromagnetic waves such as visible light, ultraviolet light, far ultraviolet light, extreme ultraviolet light (EUV), X-rays, and γ-rays; and charged particle beams such as electron beams and α-rays, depending on the line width of the intended pattern [0251].
Response to Arguments
Due to the amendment filed April 23, 2026 of instant claim 1, the 102(a)(1) rejection over Hatakeyama has been withdrawn. Applicant’s arguments with regard to this rejection have been considered but are moot due to the amendment of instant claim 1.
Applicant’s arguments regarding the 103 rejection over Hatakeyama have been fully considered but they are not persuasive. Applicant argues Hatakeyama does not teach or suggest a nitrogen-containing cation having a carboxy group whose hydrogen is substituted by a tertiary hydrocarbyl group having any one of formulae (2)-1 to (2)-8. Ammonium Salt 5 of Hatakeyama is not positioned as a tertiary hydrocarbyl group substituting the hydrogen of a carboxy group, but rather is part of a different ester architecture.
The Examiner respectfully disagrees. While the current rejection no longer explicitly relies on Ammonium Salt 5 of Hatakeyama, the general teachings of Hatakeyama still encompass the instant claims. Specifically, claim 1 defines R as “a group having any one of the formulae (2)-1 to (2)-8” which is to be interpreted as both a direct bond connecting the formulae (2)-1 to (2)-8 to the oxygen atom of formula (1) AND a linking group connecting the formulae (2)-1 to (2)-8 to the oxygen atom of formula (1). Thus, when general formula (Ac) of Hatakeyama is modified such that the ester group of Ammonium Salt 5 is reversed, the compound is equivalent to formula (1) of instant claim 1 when R is a group having the formula (2)-1. The Examiner suggests amending claim 1 to recite “R is represented by any one of formula (2)-1 to (2)-8”.
Applicant's arguments regarding the 103 rejection over Namai in view of Ichikawa have been fully considered but they are not persuasive. Applicant argues as acknowledged by the Office Action, Namai does not teach an androstane structure as the polycyclic group R4. The Office Action relies on substituting Ichikawa’s formula (W-I) into Namai’s formula (1-1). However, Ichikawa’s L1 in chemical structure I is defined as “L1 and L2 each independently represent an alkanediyl group or the like”. In contrast, Namai’s structure defines X as -OR4 or -NR5R6, where R4 is a monovalent organic group having 1 to 20 carbon atoms. These features represent fundamentally different structural positions and chemical roles. In addition, Ichikawa does not teach or suggest an androstane structure having any one of formulae (2)-1 to (2)-8 nor do Namai or Ichikawa teach or suggest a nitrogen-containing cation having a carboxy group whose hydrogen is substituted by a tertiary hydrocarbyl group having any one of formulae (2)-1 to (2)-8.
The Examiner respectfully disagrees. Ichikawa defines L1 and L2 in formula (I) as “wherein L1 and L2 are each independently represent an alkanediyl group having 1 to 12 carbon atoms, methylene groups constituting the alkanediyl groups may be replaced by oxygen atoms, -NR5- (R5 represents hydrogen atoms or alkyl groups having 1 to 6 carbon atoms), or carbonyl groups, and hydrogen atoms contained in the alkanediyl group may be substituted by fluoro atoms or hydroxy groups” [0018] such that when L1 of Ichikawa is an alkanediyl group substituted by both a carbonyl group and an oxygen atom and W is formula (W-I), it corresponds to Namai’s -L-C=O-OR4 group. Additionally, group (W-I) of Ichikawa indicates that there can be multiple R1 groups and they can be at any position on the ring and the ring itself can be connected at any position [0018]. Therefore, R1 can be attached on the same carbon atom as the attachment point to the nitrogen-containing cation demonstrating a tertiary hydrocarbyl group having formula (2)-1. Thus, the combined teachings of Namai and Ichikawa still encompass that of the instant claims.
Due to the amendment of instant claim 1 together with Applicant’s arguments, the double patenting rejections over U.S. Patent No. 11,435,665, U.S. Patent No. 11,774,853, U.S. Patent No. 11,415,887, U.S. Patent No. 11,720,018, U.S. Patent No. 11,204,553, U.S. Patent No. 11,644,753, U.S. Patent No. 11,733,608, U.S. Patent No. 11,846,884, and U.S. Patent No. 12, 411, 407, and copending application No. 17/969,059 have been withdrawn.
Due to the cancelation of claim 3, the 112(d) rejection has been withdrawn.
Conclusion
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 ANNA E MALLOY whose telephone number is (571)270-5849. The examiner can normally be reached 6:30-3:00 EST M-F.
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/Anna Malloy/Examiner, Art Unit 1737
/KEITH WALKER/Supervisory Patent Examiner, Art Unit 1735
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