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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Response to Amendment
Applicant’s Amendment filed on 03/10/2026 has been considered and is entered. Claims 12 and 25 have been amended. No new matter has been added.
Response to Arguments
Applicant’s Amendment filed 03/10/2026 has changed the scope of the claims to render the claims’ scope outside that of the prior art examples pointed to in the prior art rejections over 35 USC 103. As such, these rejections are withdrawn.
After further search and consideration, a new grounds of rejection are made over claim 12, 25, and dependents therefrom as set forth in the body of the rejection.
Regarding the arguments made:
Concerning the assertions concerning the degradation of molecular weight of disulfide-bond-containing compounds – Hiroi is not required to address a limitation that is not reflected in the claims. The claims do not mention storage stability. Further - if the degradation phenomenon described by applicant is inherent to polymers having disulfide bonds therein – which appears to be the thrust of applicants’ argument, then this phenomenon is present in the polymers of Hiroi regardless of its discussion or lack thereof as Hiroi demonstrably has a disulfide bond-containing polymer meeting the limitations of the claims as discussed below and in the prior office action.
Based on the combination of references set forth in the rejection, it appears the claimed property – the radical trapping functionality - would be met. The USPTO does not possess the laboratory facilities to test the properties of the referenced or claimed materials. As a reasonable prima facie case of obviousness has been set forth, the burden shifts to applicant to demonstrate that the properties would not be present.
The instant claims identify radical trapping agents by name. As such, the chemical compounds there named inherently function as radical trapping agents, and the context of the claim discloses only their presence and not their specific purpose: the claim language does not, for example, carve out a limitation setting forth that the radical trapping agents are present specifically to prevent molecular weight degradation. Evidence to abet a position that the suppression of molecular weight degradation as argued by applicant would be considered.
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) 12-18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hiroi et al (US 8318410 B2) and Elce et al (US 20160326292 A1)
As a matter of claim interpretation – claim 12 recites that “the claimed radical trapping agent is at least one member selected from the group consisting of:” and as such any singular instance of a thioether as further delimited by the claim, or a naphthalene derivative, or a hindered amine compound, or an ultraviolet absorber as further delimited by the claim, or thermal polymerization inhibitor as further delimited by the claim meets the limitations of the radical trapping agent.
Regarding Claims 12-16, Hiroi teaches a resist underlayer film forming composition having a polymer with a disulfide bond in the backbone, and a solvent. The polymer is described as a formed by the reaction of a diepoxy compound and a dicarboxylic acid having a disulfide bond, or combinations of one or more of each compound (Abstract).
The polymer of Hiroi is discussed from Column 2 Line 30 to Column 7 Line 50, and in the synthesis examples from Column 9 to Column 15 line 34, wherein the polymer is formed from exemplary compounds having a diepoxy compound (A)-(h) and a disulfide-bearing dicarboxylic acid compound (i)-(k), some of which are replicated below:
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The above constituent monomer units form a polymer as described in Column 2 Lines 30-64, where a catalyst may be used to activate the epoxy group such as a quaternary phosphonium or ammonium salt.
The polymer contains a disulfide bond, and as is laid out in the limitations of claim 13 and 14 is further the reaction product of a bifunctional compound comprising a disulfide bond and a different bifunctional compound having a C6 aromatic ring structure (b-d) or heterocyclic structure (a and f)
Hiroi comprises a solvent such as PGME or PGMEA, a crosslinking catalyst and a crosslinkable compound or crosslinking agent (Column 8 Lines 25 to Column 9 Line 8) (claim 15) where the crosslinking catalyst is a sulfonic acid such as camphorsulfonic acid or triflic acid and the crosslinkable compound is a compound such as but not limited to hexamethoxymethylmelamine (claim 16).
Hiroi does not explicitly disclose a radical trapping agent.
This limitation is met by Elce
Elce is concerned with a polymer composition for an imageable film, wherein exposure to actinic radiation allows for the imaging of the radiation-sensitive layer for lithographic processing (Introduction, Figs2-5).
The polymer composition of Elce is discussed from [0015]-[0164], comprising a polymer ([0042]-[0131] and further components such as quinone diazides, epoxies, as well as stabilizers such as antioxidants, coupling agents, leveling agents, and plasticizers. A specific antioxidant called out by the reference includes pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) (see claim 12, page 2, final line) the instant specification [0073]), also called by the trade name IRGANOX 1010 (also see instant specification [0073]). Elce includes this antioxidant in an amount of 0.89 parts by weight in a composition having 15.48 parts of component, or 5.7wt%.
Elce ascribes improved composition stability to the inclusion of these components. A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by including the component from Elce into the composition of Hiroi to arrive at a composition having improved stability.
Regarding Claim 17 and 18, Hiroi discloses the limitations of the claims as discussed above regarding claim 12.
Hiroi does not disclose a specific experimental embodiment that meets all claim limitations present in the instant claim.
These limitations are met by the general disclosure of Hiroi.
Hiroi discloses the composition for forming an underlayer can be used in a resist pattern formation process, described from Column 7 Line 18 to Line 52 and Column 21 Line 16 to Line 45, wherein the resist underlayer film forming composition is deposited onto a semiconductor substrate by way of a spin-coating process, then baked on a hot-plate to form a film. Afterwards, a resist composition is applied to the underlayer film and baked to form a photoresist film. The assembly is then exposed to a radiation source, then developed.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of Hiroi, which discloses a known method for treating a known composition (the composition of Hiroi and Elce discussed regarding claim 12) to arrive at a predictable result – a patterned resist and underlayer assembly.
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Hiroi et al (US 8318410 B2) and Elce et al (US 20160326292 A1) as applied to claim 12 above, and further in view of Anno et al (JP2017120359A).
Regarding Claim 19, Hiroi and Elce disclose the limitations of the claim as discussed above regarding claim 12. Additionally disclosed are methods for manufacturing a semiconductor device comprising the coating of a substrate, coating the underlayer coating with a resist, and then exposing and developing the resist.
Hiroi and Elce do not disclose a step of transferring a pattern to a substrate by way of etching an underlayer film after development of a resist, and then etching the substrate by way of the etched underlayer film.
This limitation is met by Anno.
Anno discloses a material and method for forming an underlayer film and a process of semiconductor manufacturing. The underlayer film of the reference is composed of a siloxane polymer ([0033]-[0085], a multifunctional thiol compound ([0086]-[0098]), a solvent, and a crosslinking agent ([0186]).
In the section “Pattern formation method” ([0153]-[0165]), the steps for processing a substrate is provided by way of coating an underlayer film composition atop a substrate to form a film, forming a second underlayer film (the composition described above) atop the first film, forming a resist layer atop the underlayer film stack, and then exposing and developing the resist film to form a pattern. Afterwards, the resist film pattern is used as a mask to etch the underlayer stack and transfer the pattern to the substrate.
The claim language uses “comprising” and as such additional layers and unrecited steps are not excluded. A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by way of the disclosures and teachings of Hiroi and Anno, using a known composition for photopatterning from Hiroi and Elce to be added or substituted into a known process from Anno to arrive at a patterned semiconductor substrate with high pattern transfer resolution.
Claims 20 and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Hiroi et al (US 8318410 B2) and Elce et al (US 20160326292 A1) as applied to claim 12 above, and further in view of Murakami et al (JP2015028602A).
Regarding Claim 20 and 22, Hiroi and Elce disclose the limitations of the claim as discussed above regarding claim 12 above.
Hiroi and Elce however do not teach a naphthalene derivative radical trapping agent meeting the limitations of the claim.
This limitation is met by Murakami.
Murakami discloses a colored curable composition, cured film using same, color filter, and a method of manufacturing such.
The composition of Murakami comprises a colored dye such as a phthalocyanine complex, a polymer comprising the dye complex, initiator, pigment dispersant, solvent ([0001]-[0099] and other components such as a radical trapping agent, wherein the radical trapping agent may be a naphthalene derivative such as 1,4-dihydroxynaphthalene, 6-amino-2,3-dihydro-5,8-dihydroxynaphthalene-1,4-dione, 6-methylamino-2,3-dihydro-5,8-dihydroxynaphthalene-1,4-dione, and others recited in [0101]. The radical trapping agent may also be a thioether compound such as didodecyl thiodipropionate and others of those recited in [0102], or a hindered amine compound so long as the hindered amine compound meets the partial structural limitations of Formula 51 in [103]:
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Where R1-R4 each may be H or an alkyl group, and R5 is an alkyl, alkoxy, or aryloxy group.
A person of ordinary skill in the art would have found it obvious to incorporate the radical trapping agents of Murakami into the composition of Elce and Hiroi, the use of such amounting to the use of known substances for a known purpose – to trap radicals and prevent degradation – to affect or arrive at a predictable result of a composition having improved stability.
Claim 24 is rejected under 35 U.S.C. 103 as being unpatentable over Hiroi et al (US 8318410 B2) and Elce et al (US 20160326292 A1) as applied to claim 12 above, and further in view of Shibasaki et al (US 20120111620 A1).
Regarding Claim 24, Hiroi and Elce disclose the limitations of the claims as set forth regarding claim 12 above.
However, none of the specific compounds shown in claim 24 are present in the experimental examples of the references, though Elce does make reference to antioxidant components.
This limitation is met by Shibasaki.
Shibasaki discloses a photosensitive resin composition comprising a photopolymerization initiator, a carboxylic acid-based resin, and an ethylenically unsaturated compound (Abstract).
Shibasaki details the aforementioned compositional components from [0021]-[0082].
Shibasaki also discloses additional components such as dyes/colorants. Additional components also include antioxidants – wherein one form of antioxidant ascribed to the composition includes (but are not limited to) a radical scavenger ([0141] and [0142]) such as bis(2.2.6,6-tetramethyl-4-piperidyl)-sebacate, and 4-methoxyphenol.
Further components include UV absorbers including those listed [0148]-[0154] such as phenyl salicylate, 2-(2’-hydroxy -5'-methylphenyl)benzotriazole, and 2-hydroxy-4-n-octyloxybenzophenone.
Further components include thermal polymerization inhibitors such as those listed in [0164], including but are not limited to 4-methoxyphenol which is otherwise known as p-methoxyphenol, and 2,6-di-t-butyl-4-cresol which is also be presented as 2,6-di-t-butyl-p-cresol (Formula R-1 – Claim 24). Shibasaki also acknowledges Irganox 1010 at [0143] (see discussion above regarding claim 12) in its discussion of stabilizing additive components from [0141]-[0164]. The art recognizes that both of these components may be used in the stabilization of a photosensitive composition, and presents alternative embodiments as stabilizing agents to each other.
Shibasaki ascribes improved composition stability to the inclusion of these components, which are able to prevent the production of radicals and other deteriorative effects. A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by including and/or substituting these components from Shibasaki into the composition of Hiroi and Elce to arrive at a composition having improved stability.
Claim 25 is rejected under 35 U.S.C. 103 as being unpatentable over Hiroi et al (US 8318410 B2), Elce et al (US 20160326292 A1) and Shibasaki et al (US 20120111620 A1)
Regarding Claim 25, Hiroi teaches a resist underlayer film forming composition having a polymer with a disulfide bond in the backbone, and a solvent. The polymer is described as a formed by the reaction of a diepoxy compound and a dicarboxylic acid having a disulfide bond, or combinations of one or more of each compound (Abstract).
The polymer of Hiroi is discussed from Column 2 Line 30 to Column 7 Line 50, and in the synthesis examples from Column 9 to Column 15 line 34, wherein the polymer is formed from exemplary compounds having a diepoxy compound (a)-(h) and a disulfide-bearing dicarboxylic acid compound (i)-(k), some of which are replicated below:
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The above constituent monomer units form a polymer as described in Column 2 Lines 30-64, where a catalyst may be used to activate the epoxy group such as a quaternary phosphonium or ammonium salt.
The polymer resulting from the reaction of compound (a) and compound (j) reads upon polymer P-8 of the instant claim. The polymer resulting from the reaction of compound (b) and compound (j) reads upon polymer P-6 of the instant claim. The polymer resulting from the reaction of the compound (f) and compound (j) reads upon polymer (P-7) of the instant claim.
Hiroi comprises a solvent such as PGME or PGMEA, a crosslinking catalyst and a crosslinkable compound or crosslinking agent (Column 8 Lines 25 to Column 9 Line 8).
Hiroi does not explicitly disclose pyrogallol is included in the composition
This limitation is met by Shibasaki.
Shibasaki discloses a photosensitive resin composition comprising a photopolymerization initiator, a carboxylic acid-based resin, and an ethylenically unsaturated compound (Abstract). Shibasaki details the aforementioned compositional components from [0021]-[0082].
Shibasaki also discloses additional components such as uv-absorbers and thermal polymerization inhibitors. Shibasaki recites pyrogallol as a thermal polymerization inhibitor at [0164].
Shibasaki ascribes improved composition stability to the inclusion of these components such as pyrogallol.
Shibasaki does not disclose an inclusion amount of pyrogallol in the amount required by the claims.
This limitation is met by Elce.
Elce is concerned with a polymer composition for an imageable film, wherein exposure to actinic radiation allows for the imaging of the radiation-sensitive layer for lithographic processing (Introduction, Figs2-5).
The polymer composition of Elce is discussed from [0015]-[0164], comprising a polymer ([0042]-[0131] and further components such as quinone diazides, epoxies, as well as stabilizers such as antioxidants, coupling agents, leveling agents, and plasticizers. A specific antioxidant called out by the reference includes pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate), also called by the trade name IRGANOX 1010. Elce includes this antioxidant in an amount of 0.89 parts by weight in a composition having 15.48 parts of component, or 5.7wt%. Shibasaki also acknowledges Irganox 1010 at [0143] in its discussion of stabilizing additive components from [0141]-[0164]. The art recognizes that both of these components may be used in the stabilization of a photosensitive composition, and presents alternative embodiments as stabilizing agents to each other.
Elce ascribes improved properties to the inclusion of antioxidant stabilizers in the taught compositions. Shibasaki ascribes improved composition stability to the inclusion of these components in the reference’s compositions - such as pyrogallol - which are able to prevent the production of radicals and other deteriorative effects. A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by including/substituting pyrogallol from Shibasaki, in an amount taught by Elce, into the composition of Hiroi and Elce to arrive at a composition having improved stability.
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.
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/A.P.T./Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734
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