DETAILED ACTION
Claims 1 and 3-14 are pending. Claims 1 and 3 have been amended and claim 2 has 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 .
Terminal Disclaimer
The terminal disclaimer filed on February 18, 2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of copending application 18/426,723 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Claim Objections
Claim 1 is objected to because of the following informalities: Claim 1 recites a quotation mark at the end of the claim
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which should be omitted. Claim 1 also recites
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in lines 36 and 40; in line 37,
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in which the right two anions are duplicates of the left anion and also recites
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in line 53; recites
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in lines 38 and 52; and recites
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in lines 39 and 53. The duplicates should be omitted. Appropriate correction is required.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 3-14 are rejected under 35 U.S.C. 103 as being unpatentable over Thackeray et al. (U.S. 2014/0186767) in view of Hirayama et al. (U.S. 2016/0363860).
Thackeray et al. teaches a photoresist compositions of the invention may comprise: (i) a polymer; (ii) an acid generator that corresponds to Formula (I) [0016-0018] and (iii) an acid generator that corresponds to Formula (II) [0020] (claim 8) where in a preferred embodiment, the acid generator of the above Formula (I) corresponds to the following Formula (III) [0022]:
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[0022] wherein R2 and R3 are the same or different non-hydrogen substituents and may be taken together to form a ring; or either R2 or R3 may form a ring with the aromatic substituent; A is a hydrogen or non-hydrogen substituent; m is an integer from 0 to 4; T is a non-hydrogen substituent that provides an acid-labile moiety; and Z is a sulfonate anion with at least one electron withdrawing substituent in the α position of the sulfonate [0023] and in a further preferred aspect, the acid generator of the above Formula (II) corresponds to the following Formula (IV) [0024]:
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[0024] wherein R4 and R5 are the same or different non-hydrogen substituents and may be taken together to form a ring; or either R4 or R5 may form a ring with the aromatic substituent; A is a hydrogen or non-hydrogen substituent; m is an integer from 0 to 4; R6 is a non-hydrogen substituent that provides an acid-labile moiety; and Q is a carboxylate, sulfonate or sulfamate anion that does not contain an electron withdrawing group in the α position to the carboxylate, sulfonate or sulfamate moiety [0025], specifically, preferred acid generator structures for the counter cation of either the strong or weak acid generator anions as discussed and identified above include the following [0049]:
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[page 6], preferred acid generator anions that can provide a stronger acid (e.g. pKa less than 1.0) include the following [0047]:
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[0047] in which the strong acid generator is equivalent to an acid generator capable of generating a strong acid which is a sulfonic acid of instant claims 5 and 6. Thackeray et al. teaches a selection of preferred weak acid anions [0049].
Thackeray et al. does not teach a carboxylate anion selected from those shown in claim 1.
However, Hirayama et al. teaches a resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, and which includes a base component (A) which exhibits changed solubility in a developing solution under action of acid and an acid diffusion control agent (D), the base component (A) including a structural unit (a0) represented by general formula (a0-1) shown below, and the acid diffusion control agent (D) containing an acid which exhibits an acid dissociation constant of 1.5 or more [0018] in which the component (D) functions as an acid diffusion control agent, i.e., a quencher which traps the acid generated from the component (B) and the like upon exposure. In the present embodiment, as the component (D), a photodegradable base (D1) (hereafter, referred to as “component (D)”) is decomposable by exposure to lose the ability of controlling of acid diffusion can be mentioned [0405-0406], specifically, as the component (D1), at least one member selected from the group consisting of a compound (d1-1) represented by general formula shown below (d1-1) (hereafter, referred to as “component (d1-1)”), a compound (d1-2) represented by general formula (d1-2) shown below (hereafter, referred to as “component (d1-2)”) and a compound (d1-3) represented by general formula (d1-3) shown below (hereafter, referred to as “component (d1-3)”) and has a pKa of 1.5 or more may be given as examples [0413] wherein specific examples of preferable anion moieties for the component (d1-1) include the following formula (d1-1-2) [0425]:
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[0425] and specific examples of preferable anion moieties for the component (d1-3) include the following formula (d1-3-1) [0455]:
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[0455] such that the weak acid generator of Thackeray et al. having the above cation modified by the anion of Hirayama et al. is equivalent to a quencher represented by formula (1) of instant claims 1 and 3 when s is 1, r is 1, m is 0, n is 0, p is 0, q is 0, R1 is an ester bond, R2 is a C1 alkanediyl group, R3 and R4 are C1 saturated hydrocarbyl groups, Ar is a C6 1-valent aromatic group, R8 is a C6 hydrocarbyl group, and X- is a carboxylate anion
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of instant claim 1 or a sulfonamide anion of instant claim 1, specifically formula (2)-2 of instant claim 3 when R12 is a C13 hydrocarbyl group having a heteroatom and R13 is a C1 hydrocarbyl group having a heteroatom. It should be noted that the selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 65 USPQ 297 (1945). See MPEP 2144.07. In the instant case, Thackeray and Hirayama are directed to resist compositions comprising a strong acid generator and a weak acid generator while Hirayama et al. discloses additional well-known weak acid anions.
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 Thackeray et al. to include other acid generators, both strong and weak, comprising the above defined cations together with known weak acid anions such as those defined by Hirayama et al. through routine experimentation of substituting equally suitable components for the sought invention and arrive at the instant claims in order to achieve optimum contrast, LWR, CDU, and CER.
With regard to claim 4, Thackeray et al. teaches the above weak acid generator when m is 0.
Thackeray et al. does not teach when m is 1 to 5.
However, Thackeray et al. teaches the above weak acid generator is a specific example of formula (IV) [0024] where the acid-labile group cleavage product comprises a relatively bulky moiety, e.g. a carboalicyclic (non-aromatic ring with all carbon ring atoms), heteroalicyclic (non-aromatic ring with one or more N, O or S ring atoms), aromatic groups such as optionally substituted phenyl, naphthyl and anthracreneyl [0029] and acid generators (including acid generators of Formulae (I), (II), (III), (IV)) may comprise electron withdrawing moieties, which suitably may be e.g. halogen such as Cl, Br or F with F being preferred [0045].
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 above cation [page 6] to include a fluorine substituent on the ester-containing acid labile phenyl and arrive at the instant claims through routine experimentation of substituting equally suitable variables for the sought invention with a reasonable expectation of success.
With regard to claim 7, Thackeray et al. teaches the photoresist further includes a solvent generally suitable for dissolving, dispensing, and coating the components used in a photoresists [0071].
With regard to claims 9 and 10, Thackeray et al. teaches acid generators as disclosed herein are useful as the radiation sensitive component in photoresist compositions, including both positive-acting and negative-acting chemically amplified resist compositions [0051] (claim 10) and are also suitably used with polymers that comprise repeat units containing aromatic groups, such as optionally substituted phenyl including phenol, optionally substituted naphthyl, and optionally substituted anthracene. Optionally substituted phenyl (including phenol) containing polymers are particularly suitable for many resist systems, including those imaged with EUV and e-beam radiation. For positive-acting resists, the polymer also preferably contains one or more repeat units that comprise acid-labile groups [0053] and exemplary acid-deprotectable monomers include the following [0055]:
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[0055] wherein Ra is independently H, F, --CN, C1-10 alkyl, or C1-10 fluoroalkyl [0054] which is equivalent to a base polymer comprising repeat units represented by formula (a1) of instant claim 9 when RA is hydrogen or methyl, X1 is a single bond, and R21 is an acid labile group.
With regard to claim 11, Thackeray et al. teaches Preferred monomers used for the formation of such polymers include: an acid-deprotectable monomer having the following formula (V), a lactone-containing monomer of the following formula (VI), a base-soluble monomer of the following formula (VII) for adjusting dissolution rate in alkaline developer, and a photoacid-generating monomer of the following formula (VIII), or a combination comprising at least one of the foregoing monomers [0054] and exemplary acid generating monomers include the following [0064]:
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[0064] which is equivalent to a repeat unit represented by formula (f2) of instant claim 11 when RA is methyl, Z2 is an ester bond, Z3 is a single bond, Z3 is methylene, R33 and R44 are C6 hydrocarbyl groups which are bonded to form a ring with the sulfur atom to which they are attached, and R35 is a C18 hydrocarbyl group containing three heteroatoms.
With regard to claim 12, Thackeray et al. teaches surfactants include fluorinated and non-fluorinated surfactants, and are preferably non-ionic [0070].
With regard to claims 13 and 14, Thackeray et al. teaches a method of forming an electronic device includes (a) applying a layer of a photoresist composition including on a surface of the substrate; (b) patternwise exposing the photoresist composition layer to activating radiation; and (c) developing the exposed photoresist composition layer to provide a resist relief image [0076] in which patternwise exposure is carried out using an exposure tool such as a stepper, in which the film is irradiated through a pattern mask and thereby is exposed pattern-wise. The method preferably uses advanced exposure tools generating activating radiation at wavelengths capable of high resolution including extreme-ultraviolet (EUV) or e-beam radiation [0078].
Response to Arguments
Due to the amendment filed February 18, 2026 of instant claim 1, the 103 rejection of instant claims 1-14 over Thackeray have been withdrawn. Applicant’s arguments with regard to this rejection have been considered but are moot due to the amendment of instant claim 1. However, Thackeray is still being used as prior art together with previously cited but not relied upon prior art Hirayama because Thackeray continues to teach the claimed cation for a weak acid generator (quencher).
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 8:00-4:30 EST M-F.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark Huff can be reached at 571-272-1385. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Anna Malloy/Examiner, Art Unit 1737
/MARK F. HUFF/Supervisory Patent Examiner, Art Unit 1737
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