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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 01/07/2026 has been entered.
Response to Amendment
Applicant’s Amendment filed 01/07/2026 has been entered and is being considered. Claim 15 has been canceled. Claim 1 has been amended.
Response to Arguments
Regarding Applicant’s Amendments and arguments based thereon - concerning the language of now-canceled claim 15 moved up into claim 1 – language requiring that the functional group R1 be a C1-C5 fluorinated alkoxy group (See Claims, 01/07/2026, Page 4): This language was already present in the original claim, along with the limitation of a C1-C5 fluorinated alkyl group (See Claims, 01/07/2025, Page 2). The amended claim 1 does not cancel the C1-C5 fluorinated alkyl group limitation as seems to be envisioned by the cancellation of claim 15 and movement of the alkoxy limitation into the claim 1, and the duplication of the subject matter of 15 without reformatting the claim results in a “broader range or limitation followed by narrow range or limitation” issue with claim interpretation.
After consideration a 35 USC 112(b) rejection is made as set forth in the body of the rejection.
The claim limitations at issue in the prior rejection are still present – the 35 USC 103 rejections as set forth in the Final rejection are maintained except over now-canceled claim 15.
However, as Applicant appears to consider the C1-C5 fluorinated alkoxy group limitation a distinguishing feature as per the arguments and amendments made, further search and consideration have been conducted with this limitation specifically in mind. So as to expedite prosecution, a new grounds of rejection over prior art are made specifically with the Applicant’s intended claim language in mind as set forth in the body of the rejection below.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-14 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 1 recites the broad recitation "R1 is each independently fluorine, a C1-C5 fluorinated alkyl group or C1-C5 fluorinated alkoxy group”, and the claim also recites "wherein R1 is a C1-C5 fluorinated alkoxy group" which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of 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) 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al (US 20130084527 A1) and Fujii et al (US 20200159118 A1).
Regarding Claim 1-4, 6-10, and 13-14, Hatakeyama discloses a positive resist composition comprising a polymer having carboxylic acid groups substituted with a phenylene-type acid labile group (abstract).
The polymer of Hatakeyama is as described from [0044]-[0092], where various subunits are described as part of the polymer.
Subunit (2) as shown below meets the limitations of claims 1-3 where:
R1/R2 are each straight/cyclic/branched C1-C8 alkyl, C6-C10 aryl, or C2-C10 alkenyl groups which may contain oxygen or sulfur (claimed RB and RC)
R3 is a fluorine or trifluoromethyl group, m is an integer of 1-5 (Claimed R1, where claimed n1 is 1-5, claimed n2 and n3 are both 0)
XA is a single bond, carboxylic ester, phenylene or naphthalene, where the carboxylic ester may bear a C1-C10 allylene group having an ester, ether, or lactone ring (Claimed ZA)
R4 is a hydrogen or methyl (Claimed RA)
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Further subunits described by the reference include phenolic subunits such as those described in [0055] to [0056], where selected units are reproduced below for clarity:
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Where the above units all meet the limitations of claim 1 by nature of bearing phenolic hydroxy groups and claim 4 for where:
(claimed) RA is a H or CH3
(claimed_ ZB is a single bond or carboxylic attachment
(claimed) subscript m2 is 0
(claimed) subscript m1 is 1-2
Further, the polymer of the reference comprises subunits d1 through
d3 as depicted below:
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Where the above units read upon claimed subunit C1 ( and as for claim 13) for where d1 has:
A carboxylic ester or amide with an attachment group, where the attached group to the carboxylic/imide group is a C1-C6 alkylene/alkenylene/phenylene group or group containing such and may have a carbonyl, ether, ester, or hydroxyl group therein (Claimed Z1+Z2, Reference R31)
Claimed R1 and R22 are each independently C1-C20 hydrocarbyl groups that may have a heteroatom and may bond together to form a ring with the sulfur atom (Reference R32 and R33)
The above reads upon claimed subunit C2(and as C2 for claim 13) for where d2 has:
A carboxylic ester or amide with an attachment group, where the attached group to the carboxylic/imide group is a C1-C6 alkylene/alkenylene/phenylene group or group containing such and may have a carbonyl, ether, ester, or hydroxyl group therein (Claimed Z3+Z4
Claimed L1 is a single bond
Claimed Rf1-Rf4 are each fluorine
Claimed A+ is a sulfonium ion where R35-R37 are each C1-C12 alkyl, C6-C12 aryl, C7-C20 aralkyl groups (claim 6 – where claimed R groups on the sulfonium cation corresponding to A+ are each C1-C20 hydrocarbyl groups)
Additional monomers recited among those that may be included include monomers having an adhesive group such as a non-phenolic hydroxyl group, lactone, ether, ester, or cyano group ([0057]):
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The above units meet the limitations of claim 7 and 13 (claimed unit (a1)) where:
Claimed ZC is a single bond
Claimed RA is a methyl group
Claimed XA is an acid-labile group free of aryl-fluorine substituents
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the above monomers, among others recited in the cited section, meet the limitations of claim 8 and 13 (claimed unit D1) for where:
claimed RA is a hydrogen or methyl
Claimed ZE is a single bond
YA is a hydrogen or a polar group containing a hydroxy group, ester group, carbonyl, and/or carboxy group
The composition taught by the reference may comprise a combination of the polymer with an organic solvent, a photoacid generator, a surfactant, and other components as described from [0097]-[0100] (claims 9 and 10).
Hatakeyama does not explicitly disclose a quencher in the form of an onium salt.
This limitation is met by Fujii.
Fujii discloses a resist composition comprising a polymer having various subunits including hydroxystyrene, acrylate esters, and other components as discussed from ([0009]-[0444].
The composition of Fujii also comprises at least one acid generator (B) component to generate acid upon exposure ([0448]-[0550].
A component (D) is also discussed, where the D component is either an organic base component or a photoacid generator that generates an acid weaker than the generator (B) to act as a quencher (See [0550]-[0616]). Fujii ascribes improved acid diffusion control and contrast between exposed and unexposed portions of the resist pattern after processing.
A person of ordinary skill in the art would have found it obvious to incorporate the quenchers of Fujii into the resist composition of Hatakeyama to arrive at a resist having improved acid diffusion control and contrast.
Regarding Claim 5, Hatakeyama describes the limitations of the claim as described above regarding claim 1.
Hatakeyama does not explicitly disclose a quencher in the form of an onium salt.
This limitation is met by Fujii.
Fujii discloses a resist composition comprising a polymer having various subunits including hydroxystyrene, acrylate esters, and other components as discussed from ([0009]-[0444].
The composition of Fujii also comprises at least one acid generator (B) component to generate acid upon exposure ([0448]-[0550].
A component (D) is also discussed, where the D component is either an organic base component or a photoacid generator that generates an acid weaker than the generator (B) to act as a quencher (See [0550]-[0616]). Fujii ascribes improved acid diffusion control and contrast between exposed and unexposed portions of the resist pattern after processing.
The quenchers of Fujii are described as d-1 through d-3 below, where D-1 and d-2 read upon claimed (1) and (2)
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These compounds are further delimited where Rd1 may be an aromatic hydrocarbon group or other group defined in [0573]-[0582] such as phenyl, ethyl, propyl, or hydroxyethyl , Rd2 may be a moeity as defined in [0587]-[0592] such as adamantyl or cyclohexyl – the carbon alpha to the sulfo group should remain non-fluorinated.
A person of ordinary skill in the art would have found it obvious to incorporate the quenchers of Fujii into the resist composition of Hatakeyama to arrive at a resist having improved acid diffusion control and contrast.
Regarding Claims 11 and 12, Hatakeyama and Fujii disclose the limitations of the claim as discussed above regarding claim 1.
Hatakeyama however fails to disclose an experimental example matching the limitations of the claims wherein a composition meeting the limitations of claim1 are used in the process delimited by these claims.
These limitations are met by the general disclosure of Hatakeyama, wherein the resist films generally disclosed by the references are applied to a substrate to form a resist film thereupon, exposed to radiation, and developed with developing solution - the radiation used in exposure may be EB, EUV, or excimer radiation. Hatakeyama asserts that the invention is best suited for patterning with such radiation.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by incorporating the resist composition of Hatakeyama and Fujii into the patterning process described by Hatakeyama – using a resist composition in a resist composition amounts to using a known composition or composition similar thereto in a known process with the expectation of predictable results – in this case a patterned resist film.
Claim(s) 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al (US 20130084527 A1), Masunaga et al (US 20180039177 A1), and Fujii et al (US 20200159118 A1).
Regarding Claim 1-4, 6-10, and 13-14, Hatakeyama discloses a positive resist composition comprising a polymer having carboxylic acid groups substituted with a phenylene-type acid labile group (abstract).
The polymer of Hatakeyama is as described from [0044]-[0092], where various subunits are described as part of the polymer.
Subunit (2) as shown below meets the limitations of claims 1-3 where:
R1/R2 are each straight/cyclic/branched C1-C8 alkyl, C6-C10 aryl, or C2-C10 alkenyl groups which may contain oxygen or sulfur (claimed RB and RC)
R3 is a fluorine or trifluoromethyl group, m is an integer of 1-5 (Claimed R1, where claimed n1 is 1-5, claimed n2 and n3 are both 0)
XA is a single bond, carboxylic ester, phenylene or naphthalene, where the carboxylic ester may bear a C1-C10 allylene group having an ester, ether, or lactone ring (Claimed ZA)
R4 is a hydrogen or methyl (Claimed RA)
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In the instance that the claimed R1 (corresponding to reference R3) is a C1-C5 fluorinated alkoxy, neither Hatakeyama nor Fujii meet this limitation.
This limitation may be met by Masunaga.
Masunaga discloses a resist composition comprising a photoacid generator and a base resin, wherein the base resin comprises structure (B2):
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Where:
RA is H/F/Me/CF3
R12 is halogen, a halogenated C2-C8 acyloxy group, a halogenated C1-C6 alkyl group, or a C1-C6 halogenated alkoxy group, or a nonhalogenated version of the aforementioned groups
The genus “halogen” has 4 members for practical purposes – F, Cl, Br, and I
A2 is a single bond or a C1-C10 straight/cyclic or branched alkyl group
Subscript s is 0 or 1, t is 0-2, c is an integer that sums with t and e to the balance of substitutable spots on the aryl ring(s), d is 0 or 1, e is 1-3
X is an acid labile group
Acid labile groups may be C4-C18 tertiary alkyl groups attached to the ring by an ether linkage (a protected phenolic group) or an ester linkage
The above subunit meets the limitations of the claim for where:
Claimed RA is H, CF3, Me, or F
Claimed ZA is a single bond (reference s is 1)
Claimed RC and RB are each independently a C1-C9 hydrocarbyl group (reference A2 for where A4 is a C3-C10 Branched hydrocarbyl group)
Claimed R1 is a Fluorine, a C1-C5 fluorinated alkyl group, or a C1-C5 fluorinated alkoxy group (Reference R12)
R2 is a C4-C10 hydrocarbyl group that contains an ether linkage (reference subscript e is 1 and subscript d is 0, X is a C4-C10 alkyl group)
Subscript n3 is 0-2 (reference subscript t is 0-2)
Masunaga ascribes improved etch resistance and resolution to the composition when a polymer comprising recurring unit (B2) among others. A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention by including the above subunit in the composition of Hatakeyama in order to improve processing parameters such as etch resistance, and/or in the alternative, including functional groups such as the fluorinated alkoxy so as to attenuate the chemical features of Hatakeyama’s subunits with the intent to modify the resultant properties towards an improved result.
Further subunits described by Hatakeyama include phenolic subunits such as those described in [0055] to [0056], where selected units are reproduced below for clarity:
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Where the above units all meet the limitations of claim 1 by nature of bearing phenolic hydroxy groups and claim 4 for where:
(claimed) RA is a H or CH3
(claimed_ ZB is a single bond or carboxylic attachment
(claimed) subscript m2 is 0
(claimed) subscript m1 is 1-2
Further, the polymer of the reference comprises subunits d1 through
d3 as depicted below:
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Where the above units read upon claimed subunit C1 ( and as for claim 13) for where d1 has:
A carboxylic ester or amide with an attachment group, where the attached group to the carboxylic/imide group is a C1-C6 alkylene/alkenylene/phenylene group or group containing such and may have a carbonyl, ether, ester, or hydroxyl group therein (Claimed Z1+Z2, Reference R31)
Claimed R1 and R22 are each independently C1-C20 hydrocarbyl groups that may have a heteroatom and may bond together to form a ring with the sulfur atom (Reference R32 and R33)
The above reads upon claimed subunit C2(and as C2 for claim 13) for where d2 has:
A carboxylic ester or amide with an attachment group, where the attached group to the carboxylic/imide group is a C1-C6 alkylene/alkenylene/phenylene group or group containing such and may have a carbonyl, ether, ester, or hydroxyl group therein (Claimed Z3+Z4
Claimed L1 is a single bond
Claimed Rf1-Rf4 are each fluorine
Claimed A+ is a sulfonium ion where R35-R37 are each C1-C12 alkyl, C6-C12 aryl, C7-C20 aralkyl groups (claim 6 – where claimed R groups on the sulfonium cation corresponding to A+ are each C1-C20 hydrocarbyl groups)
Additional monomers recited among those that may be included include monomers having an adhesive group such as a non-phenolic hydroxyl group, lactone, ether, ester, or cyano group ([0057]):
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The above units meet the limitations of claim 7 and 13 (claimed unit (a1)) where:
Claimed ZC is a single bond
Claimed RA is a methyl group
Claimed XA is an acid-labile group free of aryl-fluorine substituents
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the above monomers, among others recited in the cited section, meet the limitations of claim 8 and 13 (claimed unit D1) for where:
claimed RA is a hydrogen or methyl
Claimed ZE is a single bond
YA is a hydrogen or a polar group containing a hydroxy group, ester group, carbonyl, and/or carboxy group
The composition taught by the reference may comprise a combination of the polymer with an organic solvent, a photoacid generator, a surfactant, and other components as described from [0097]-[0100] (claims 9 and 10).
Hatakeyama does not explicitly disclose a quencher in the form of an onium salt.
This limitation is met by Fujii.
Fujii discloses a resist composition comprising a polymer having various subunits including hydroxystyrene, acrylate esters, and other components as discussed from ([0009]-[0444].
The composition of Fujii also comprises at least one acid generator (B) component to generate acid upon exposure ([0448]-[0550].
A component (D) is also discussed, where the D component is either an organic base component or a photoacid generator that generates an acid weaker than the generator (B) to act as a quencher (See [0550]-[0616]). Fujii ascribes improved acid diffusion control and contrast between exposed and unexposed portions of the resist pattern after processing.
A person of ordinary skill in the art would have found it obvious to incorporate the quenchers of Fujii into the resist composition of Hatakeyama and Masunaga to arrive at a resist having improved acid diffusion control and contrast.
Regarding Claim 5, Hatakeyama describes the limitations of the claim as described above regarding claim 1.
Hatakeyama and Masunaga do not explicitly disclose a quencher in the form of an onium salt.
This limitation is met by Fujii.
Fujii discloses a resist composition comprising a polymer having various subunits including hydroxystyrene, acrylate esters, and other components as discussed from ([0009]-[0444].
The composition of Fujii also comprises at least one acid generator (B) component to generate acid upon exposure ([0448]-[0550].
A component (D) is also discussed, where the D component is either an organic base component or a photoacid generator that generates an acid weaker than the generator (B) to act as a quencher (See [0550]-[0616]). Fujii ascribes improved acid diffusion control and contrast between exposed and unexposed portions of the resist pattern after processing.
The quenchers of Fujii are described as d-1 through d-3 below, where D-1 and d-2 read upon claimed (1) and (2)
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These compounds are further delimited where Rd1 may be an aromatic hydrocarbon group or other group defined in [0573]-[0582] such as phenyl, ethyl, propyl, or hydroxyethyl , Rd2 may be a moeity as defined in [0587]-[0592] such as adamantyl or cyclohexyl – the carbon alpha to the sulfo group should remain non-fluorinated.
A person of ordinary skill in the art would have found it obvious to incorporate the quenchers of Fujii into the resist composition of Hatakeyama and Masunaga to arrive at a resist having improved acid diffusion control and contrast.
Regarding Claims 11 and 12, Hatakeyama, Masunaga and Fujii disclose the limitations of the claim as discussed above regarding claim 1.
Hatakeyama and Masunaga however fail to disclose an experimental example matching the limitations of the claims wherein a composition meeting the limitations of claim1 are used in the process delimited by these claims.
These limitations are met by the general disclosure of Hatakeyama, wherein the resist films generally disclosed by the references are applied to a substrate to form a resist film thereupon, exposed to radiation, and developed with developing solution - the radiation used in exposure may be EB, EUV, or excimer radiation. Hatakeyama asserts that the invention is best suited for patterning with such radiation.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by incorporating the resist composition of Hatakeyama, Masunaga, and Fujii into the patterning process described by Hatakeyama – using a resist composition in a resist composition amounts to using a known composition or composition similar thereto in a known process with the expectation of predictable results – in this case a patterned resist film.
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
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734