DETAILED ACTION
Claims 16 and 19-31 are pending. Claims 16 and 21 have been amended, claims 1-15, 17, and 18 were previously canceled, and claim 31 has been added.
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 8, 2026 has been entered.
Claim Objections
Claim 16 is objected to because of the following informalities: Claim 16 recites “the Dm-anion is an anion represented by the formula (DA1) or an anion represented by the formula (DA2)”. However, formula (DA2) has been omitted. Appropriate correction is required.
Claim Interpretation
Claim 16 recites “Rd3 is hydroxy” while page 10 of the remarks recites “Rd3 is each independently hydrogen” and argues on page 11 that “the photoacid generator D1 used in Compositions 1 to 6 possesses the same anion as that recited in amended claim 16”. However, photoacid generator D1 in the instant specification is
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which corresponds with Rd3 being defined as hydrogen and not hydroxy. It is unclear if Applicant intends for Rd3 to be defined as hydroxy or hydrogen, so for examination purposes, the following rejections are based on Rd3 being defined as either hydrogen or hydroxy.
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 16 and 19-31 are rejected under 35 U.S.C. 103 as being unpatentable over Park et al. (U.S. 2021/0200084).
Park et al. teaches a polymer comprising a first repeating unit derived from a monomer comprising a hydroxy-aryl group; a second repeating unit derived from a monomer comprising a hydroxy-aryl group protected with an acetal or ketal group; a third repeating unit derived from a (meth)acrylate monomer comprising a cycloaliphatic group; and a fourth repeating unit derived from a monomer comprising an acid-sensitive group, wherein the first, the second, the third, and the fourth repeating units are different from each other. Another embodiment provides a photoresist composition comprising the polymer, a photoacid generator, and a solvent [0006-0007] wherein a specific example of the polymer includes the following tetrapolymer B-2:
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[0097] which has a cLogP of 3.06 (claim 16) wherein the leftmost repeating unit is equivalent to 55% of repeating unit (A-1) of instant claims 16 and 21 when R12-R14 are hydrogen, p11 is 0, and p15 is 1, the repeating unit second from the left is equivalent to 19% of repeating unit (A-4) of instant claims 16 and 21 when R42-R44 are hydrogen, p41 is 0, and p45 is 1 where R45 is a C5 alkyl where -CH2- is replaced with -O-, the repeating unit second from the right is equivalent to 10% of repeating unit (A-2) of instant claims 16 and 21 when R22-R24 are hydrogen and p21 is 0, and the rightmost repeating unit is equivalent to 16% of repeating unit (A-3) of instant claims 16, 21, and 31 when R32 is C1 alkyl, R33 and R34 are hydrogen, and R31 is C7 alkyl in which part of the alkyl forms a ring. Park et al. also teaches a specific example of the photoacid generator includes triphenylsulfonium trifluoromethanesulfonate [0061] which is equivalent to photoacid generator (B) represented by formula (B-1) of instant claim 16 when Bn+cation is a cation represented by formula (BC1) when nb1-nb3 are 0 and Bn-anion is an anion represented by formula (BA2) when Rb6 is a fluorine-substituted C1 alkyl in which the acid released has a known pka of -12 (claim 22). Park et al. further teaches the photoresist composition may further include one or more optional additives. For example, optional additives may include actinic and contrast dyes, anti-striation agents, plasticizers, speed enhancers, sensitizers, photo-destroyable bases, basic quenchers, surfactants, and the like, or combinations thereof [0073] (claims 19 and 20) and exemplary photo-destroyable bases include, for example, photo-decomposable cations, and preferably those also useful for preparing acid generator compounds, paired with an anion of a weak (pKa>2) acid such as, for example, a C1-20 carboxylic acid. Exemplary carboxylic acids include formic acid [0074] such that when the cation of the photo-destroyable base is triphenylsulfonium and the anion is formic acid, it is equivalent to photoacid generator (D) represented by formula (D-1) of instant claim 16 when Dm+cation is represented by formula (DC1) when nd1-nd3 are 0 and Dm-anion is represented by formula (DA1) when X is a single bond, Rd3 is hydrogen, nd3 is 1, and nd4 is 1. Park et al. also teaches the present disclosure is illustrated in more detail with reference to examples. However, these examples are exemplary, and the present disclosure is not limited thereto [0091] and while this invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims [0116]. Park et al. further teaches there is a continuing need for polymers and coating compositions that could be suitable for thick photoresist films, which have improved transmittance at exposure wavelength, excellent retention of properties after thickness trimming and etching, and increased photospeed [0005].
Park et al. does not teach a specific example comprising the above described components.
However, 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 Park et al. to include additional compositions comprising the above described components and arrive at the instant claims through routine experimentation of combining equally suitable components for the sought invention in order to achieve optimum transmittance, property retention, and photospeed.
With regard to claim 23, Park et al. teaches the polymer is typically present in the photoresist composition in an amount of from 10 to 99.9 wt %, preferably from 25 to 99 wt %, more preferably 50 to 95 wt %, based on the weight of the total solids [0054], the one or more PAGs are typically present in the photoresist compositions in an amount of from 0.1 to 10 wt % and preferably from 0.1 to 5 wt %, based on total solids [0071], and the solvent can be present in the photoresist compositions in an amount of from 40 to 99 wt %, preferably from 40 to 70 wt %, based on the total weight of the photoresist composition [0072] which overlap the instantly claimed ranges. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).
With regard to claim 24, Park et al. teaches the solvent may be an aliphatic hydrocarbon (such as hexane, heptane, and the like), an aromatic hydrocarbon (such as toluene, xylene, and the like), a halogenated hydrocarbon (such as dichloromethane, 1,2-dichloroethane, 1-chlorohexane, and the like), an alcohol (such as methanol, ethanol, 1-propanol, iso-propanol, tert-butanol, 2-methyl-2-butanol, 4-methyl-2-pentanol, and the like), water, an ether (such as diethyl ether, tetrahydrofuran, 1,4-dioxane, anisole, and the like), a ketone (such as acetone, methyl ethyl ketone, methyl iso-butyl ketone, 2-heptanone, cyclohexanone, and the like), an ester (such as ethyl acetate, n-butyl acetate, propylene glycol monomethyl ether acetate (PGMEA), ethyl lactate, hydroxyisobutyrate methyl ester (HBM), ethyl acetoacetate, and the like), a lactone (such as gamma-butyrolactone (GBL), epsilon-caprolactone, and the like), a nitrile (such as acetonitrile, propionitrile, and the like), aa polar aprotic solvent (such as dimethyl sulfoxide, dimethyl formamide, and the like), or a combination thereof [0072].
With regard to claims 25-30, Park et al. teaches also provided is a coated substrate formed from the photoresist composition. Such a coated substrate may include: (a) a substrate, and (b) a layer of the photoresist composition disposed over the substrate [0078] and further provided is a method of forming a pattern that includes applying a layer of the photoresist composition on a substrate; drying the applied photoresist composition to form a photoresist composition layer; exposing the photoresist composition layer to activating radiation; heating the exposed photoresist composition layer; and developing the exposed composition layer to form a resist pattern [0080] in which the coated wafer is spun to remove solvent, and soft-baked on a hot plate to remove residual solvent and reduce free volume to densify the film. The soft-bake temperature is typically from 90 to 170° C, for example, from 110 to 150° C [0081] and the photoresist may, when used in one or more such pattern-forming processes, be used to fabricate semiconductor devices such as memory devices, processor chips (CPUs), graphics chips, optoelectronic chips, and other such devices. The pattern forming method may further include forming a staircase pattern in the substrate using the photoresist composition layer as an etch mask, wherein the staircase patter comprises a plurality of stairs [0087-0088]. The patterned film of Park et al. is the same as instantly claimed, therefore it is expected to satisfy Tr/T = 0 to 25%, absent any evidence to the contrary (claim 28).
Claims 16, 19-28, 30, and 31 are rejected under 35 U.S.C. 103 as being unpatentable over Namai (U.S. 2016/0363859).
Namai teaches the radiation-sensitive resin composition according to an embodiment of the present invention contains the polymer (A), the acid generator (B) and the salt (C). The radiation-sensitive resin composition may contain, as a favorable component, a polymer having a greater mass percentage content of fluorine atoms than that of the polymer (A) (hereinafter, may be also referred to as “(D) polymer” or “polymer (D)”), (E) a solvent, (F) a localization accelerator and/or other acid diffusion controller than the salt (C) (hereinafter, may be also referred to as “(G) other acid diffusion controller” or “other acid diffusion controller (G)) [0013] wherein a specific example of the polymer includes Polymer 5 which comprises 35 mol% monomer M-5 and 65 mol% monomer M-4 [0335] which are the following:
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[0332] in which monomer M-1 produces a p-hydroxystyrene structural unit which is equivalent to repeating unit (A-1) of instant claim 16 when R12-R14 are hydrogen, p11 is 0, and p15 is 1, and monomer M-5 produces a structural unit equivalent to repeating unit (A-3) of instant claims 16 and 31 when R33 and R34 are hydrogen, R32 is C1 alkyl, and P31 is C12 alkyl where part of the alkyl forms a ring. Polymer A-5 has a cLogP value of 3.4785 which is outside the claimed range of 2.76 to 3.35.
However, Namai teaches the adamantyl structural unit used in Polymer A-5 is a specific example of the following structural unit [0059]:
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[0059] where R1 represents a hydrogen atom or a methyl group [0022] which is equivalent to repeating unit (A-3) of instant claims 16 and 31 when R33 and R34 are hydrogen, R32 is hydrogen or C1 alkyl, and P31 is C12 alkyl where part of the alkyl forms a ring. The cLogP value of 2-ethyladamantyl methacrylate is higher than that of 2-ethyladamantyl acrylate. Namai also teaches the lower limit of the proportion of the structural unit (I) with respect to the total structural units constituting the polymer (A) is preferably 10 mol %, more preferably 20 mol %, still more preferably 30 mol %, and particularly preferably 35 mol %. The upper limit of the aforementioned proportion is preferably 80 mol %, more preferably 75 mol %, still more preferably 70 mol %, and particularly preferably 60 mol %. When the proportion of the structural unit (I) falls within the above range, the LWR performances, etc. of the radiation-sensitive resin composition may be further improved [0062] and when the polymer (A) has the structural unit (III), the lower limit of the proportion of the structural unit (III) with respect to the total structural units constituting the polymer (A) is preferably 10 mol %, more preferably 30 mol %, and still more preferably 50 mol %. The upper limit of the aforementioned proportion is preferably 90 mol %, more preferably 80 mol %, and still more preferably 75 mol %. When the proportion of the structural unit (III) falls within the above range, the sensitivity of the radiation-sensitive resin composition may be further improved [0019] which overlaps the claimed range of 40 to 80% (claim 21). Namai further teaches Obviously, numerous modifications and variations of the present invention are possible in light of the above teachings. It is therefore to be understood that within the scope of the appended claims, the invention may be practiced otherwise than as specifically described herein [0382] such that when the structural unit M-5 in Polymer A-5 is substituted with the acrylate version or when the mol % of said structural unit is provided in a smaller amount, the polymer of Namai achieves a cLogP value within the instantly claimed range.
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 Namai and arrive at the instant claims through routine experimentation of substituting equally suitable structural units and/or optimizing its concentration in order to achieve optimum LWR and sensitivity.
Namai also teaches a specific example of the acid generating agent (B) includes the following formula (B-5):
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[0345] which is equivalent to photoacid generator (B) represented by formula (B1) of instant claim 16 when Bn+cation is a cation represented by formula (BC1) when nb1-nb3 are 0 and Bn-anion is an anion represented by formula (BA3) when two Rb7 are bonded to each other to form a fluorine-substituted heterocyclic structure in which the acid released has a known pka of -11.55 (claim 22). Namai further teaches a specific example of salt (C) includes the following formula (Z-2):
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[0354] which is equivalent to a photoacid generator (D) represented by formula (D-1) of instant claim 16 when Dm+cation is a cation represented by formula (DC1) when nd1-nd3 are 1 and each Rd1 is a C4 alkyl and Dm-anion is represented by formula (DA1) when X is a single bond, Rd3 is hydroxy, nd3 is 1, and nd4 is 1. Namai also teaches the radiation-sensitive resin composition and the resist pattern-forming method according to the embodiments of the present invention enable a resist pattern that is superior in LWR performances, CDU performances, resolution and rectangularity of cross-sectional shape to be formed while superior depth of focus and MEEF performances are exhibited. Therefore, these can be suitably used for pattern formation in production of semiconductor devices, and the like, in which further progress of miniaturization is expected [0381].
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 Namai and arrive at the instant claims through routine experimentation of substituting equally suitable components in order to achieve optimum LWR and sensitivity.
With regard to claim 19, Namai teaches a specific example of the other acid diffusion control agent (G) includes the following formula (G-3):
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[0363] which is equivalent to a basic compound (E) of instant claim 19.
With regard to claim 20, Namai teaches the radiation-sensitive resin composition may contain other optional component than the components (A) to (G). The other optional component is exemplified by a surfactant, an alicyclic skeleton-containing compound, a sensitizing agent, and the like [0309].
With regard to claim 23, Namai teaches the lower limit of the content of the acid generating agent (B) with respect to 100 parts by mass of the polymer (A) is preferably 0.1 parts by mass, more preferably 0.5 parts by mass, still more preferably 1 part by mass, particularly preferably 5 parts by mass, further particularly preferably 10 parts by mass, and most preferably 15 parts by mass. The upper limit of the aforementioned content is preferably 50 parts by mass, more preferably 40 parts by mass, still more preferably 30 parts by mass, and particularly preferably 25 parts by mass [0188], and the lower limit of the solid content concentration of the radiation-sensitive resin composition is preferably 0.1% by mass, more preferably 0.5 parts by mass, and still more preferably 1% by mass. The upper limit of the aforementioned solid content concentration is preferably 50% by mass, more preferably 30% by mass, and still more preferably 20% by mass [0314] (i.e. solvent is 50 mass% to 99.9 mass%) and in the Examples, the polymer (A) is present in about 3 mass% [0365] which overlap the instantly claimed ranges. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).
With regard to claim 24, Namai teaches the solvent (E) is exemplified by alcohol solvents, ether solvents, ketone solvents, amide solvents, ester solvents, hydrocarbon solvents, and the like [0260].
With regard to claims 25-28 and 30, Namai teaches the resist pattern-forming method according to another embodiment of the present invention includes: the step of forming a resist film (hereinafter, may be also referred to as “resist film-forming step”); the step of exposing the resist film (hereinafter, may be also referred to as “exposure step”); and the step of developing the resist film exposed (hereinafter, may be also referred to as “development step”) [0316] wherein it is to be noted that after the radiation-sensitive resin composition is applied on the substrate, soft baking (heating) (hereinafter, may be also referred to as “SB”) may be carried out to evaporate the solvent [0318] for the production of semiconductor devices [0012]. The patterned film of Namai is the same as instantly claimed, therefore it is expected to satisfy Tr/T = 0 to 25%, absent any evidence to the contrary (claim 28).
Claim 29 is rejected under 35 U.S.C. 103 as being unpatentable over Namai (U.S. 2016/0363859) as applied to claim 27 above, and further in view of Park et al. (U.S. 2021/0200084).
With regard to claim 29, Namai teaches the above pattern-forming method for semiconductors devices.
Namai does not teach additional processing steps including using the resist pattern as a mask.
However, Park et al. teaches the photoresist may, when used in one or more such pattern-forming processes, be used to fabricate semiconductor devices such as memory devices, processor chips (CPUs), graphics chips, optoelectronic chips, and other such devices. The pattern forming method may further include forming a staircase pattern in the substrate using the photoresist composition layer as an etch mask, wherein the staircase patter comprises a plurality of stairs [0087-0088]. The rationale to modify or combine the prior art does not have to be expressly stated in the prior art; the rationale may be expressly or impliedly contained in the prior art or it may be reasoned from knowledge generally available to one of ordinary skill in the art, established scientific principles, or legal precedent established by prior case law. In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988). In the instant case, both Namai and Park et al. are directed to resist compositions suitable for semiconductor devices while Park et al. also teaches additional steps well known in the resist art.
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 to include additional steps such as use of an etch mask as taught by Park et al. and arrive at the instant claims through routine experimentation of combining known steps commonly performed in the semiconductor art.
Response to Arguments
Due to the amendment filed May 8, 2026 of instant claim 16, the 103 rejection over Suzuki has been withdrawn. Applicants’ arguments with regard to this rejection have been considered but are moot due to the amendment of instant claim 16.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. U.S. 2011/0014570.
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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