DETAILED ACTION
Claims 1-4, 8-14, 21-24, 26, and 27 are pending. Claims 1 and 21 have been amended and claims 5-7, 15-20, 25, 28, and 29 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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 July 16, 2025 has been entered.
Claim Interpretation
Claims 1 and 21 recite “in the formula (X-3), Rc1, Rc2 and Rc3 are each independently a substituted or unsubstituted, aromatic hydrocarbon group having a carbon number of 6 to 12”. The Examiner is interpreting the defined number of carbon atoms to be for the aromatic hydrocarbon only and does not encompass the possible substituent. Claims 1 and 21 also recite “any of the sulfonium cation and the iodonium cation is represented by at least one of formula (X-2) to formula (X-5)”. The Examiner is interpreting this language to mean the radiation-sensitive acid generator may be represented by formula (X-2) to (X-5) but it is not required. If Applicant’s intent is for the radiation-sensitive acid generator to comprise only cations represented by formula (X-2) to formula (X-5), the Examiner suggests replacing “any of the sulfonium cation and the iodonium cation is” with --all of the sulfonium cations and the iodonium cations are--.
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 § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 21-24, 26, and 27 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Kojima et al. (U.S. 2020/0183275).
Kojima et al. teaches a resist composition in Example 1 comprising 100 parts by mass polymer (A1-1), 15.0 parts by mass acid generator (B1)-1, 5.0 parts by mass acid diffusion control agent (D0)-1, and 6000 parts by mass solvent S-1 were mixed and dissolved [0695] wherein (A1-1) is the following:
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[0700] which is equivalent to a resin comprising a structural unit having a phenolic hydroxyl group of instant claim 21; (B1-1) is the following:
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[0706] which is equivalent to a radiation-sensitive acid generator of instant claim 21 having a pka of -3.39 having a sulfonium cation represented by formula (X-3) when Rc1 and Rc2 are unsubstituted aromatic hydrocarbon groups having a carbon number of 6 and Rc3 is a substituted, aromatic hydrocarbon group having a carbon number of 6; and (D0-1) is the following:
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[0707] which is equivalent to a compound represented by formula (1) of instant claims 21 and 22, specifically formula (1-1) of instant claims 23 and 24 when n is 2, q is 0, m is 0, and Z+ is represented by formula (X-3) when Rc1 to Rc3 are unsubstituted aromatic hydrocarbon groups having a carbon number of 6 having a pka of 1.30. The calculated mol% for the compound (1), assuming parts by mass to be grams, is 50 mol% with respect to the acid generator (claim 21). Kojima et al. also teaches an 8-inch silicon substrate to which a hexamethyldisilazane (HMDS) had been applied was coated with the resist composition of each example using a spinner, and a prebake (PAB) treatment was performed thereon on a hot plate at a temperature of 110° C for 60 seconds so that the hot plate was dried to form a resist film having a film thickness of 50 nm. Next, drawing (exposing) was performed on the resist film at an accelerating voltage of 100 kV such that the target size was set to a line width of 50 nm to 20 nm and 1:1 line and space pattern using an electron beam lithography device JEOL-JBX-9300FS (manufactured by JEOL Ltd.). Thereafter, a post exposure bake (PEB) treatment was performed thereon at 90° C for 60 seconds. Subsequently, alkali development was performed at 23° C for 60 seconds using a 2.38% by mass tetramethylammonium hydroxide (TMAH) aqueous solution “NMD-3” (trade name, manufactured by TOKYO OHKA KOGYO CO., LTD.) [0711-0713] (claims 26 and 27).
Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216.
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 1-4 and 8-14 are rejected under 35 U.S.C. 103 as being unpatentable over Komuro et al. (U.S. 2013/0224658) in view of Namai (U.S. 2014/0186771).
Komuro et al. teaches a resist composition according to the present invention includes a base component (A) that exhibits changed solubility in a developing solution by the action of acid, a photoreactive quencher (C) and an acid generator component (B) which generates acid upon exposure [0032] in which in the case where the resist composition of the present invention is a resist composition which forms a positive pattern in an alkali developing process and a negative pattern in a solvent developing process, it is preferable to use a base component (A0) which exhibits increased polarity by the action of acid [0049] and the component (A0) may be a resin component (A1) that exhibits increased polarity under the action of acid, a low molecular weight material (A2) that exhibits increased polarity under the action of acid, or a mixture thereof [0053] wherein component (A1) preferably has a structural unit (a1) containing an acid decomposable group that exhibits increased polarity by the action of acid, a structural unit (a2) containing an --SO2-- containing cyclic group or a lactone-containing cyclic group, and a structural unit (a3) containing a polar group [0055-0057] and specific examples of the structural unit (a3) include structural units derived from (α-substituted) acrylic acid and structural units represented by general formulas (a3-11) to (a3-13) [0379] such as the following formula (a3-11-2):
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[0385] wherein R” is a hydrogen atom, a methyl group or a trifluoromethyl group [0385] which is equivalent to a resin comprising a structural unit having a phenolic hydroxyl group derived from hydroxystyrene of instant claims 1 and 11. Komuro et al. also teaches the amount of the structural unit (a3) based on the combined total of all structural units constituting the component (A1) is preferably 0 to 85 mol %, and more preferably 0 to 80 mol % [0403] (claim 12). Komuro et al. further teaches a specific example of acid generator (B) includes the following (B)-4:
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[page 81] which is equivalent to a radiation-sensitive acid generator of instant claim 1 having a pka of -3.39 having a sulfonium cation represented by formula (X-3) when Rc1 and Rc2 are unsubstituted aromatic hydrocarbon groups having a carbon number of 6 and Rc3 is a substituted aromatic hydrocarbon group having a carbon number of 6. Komuro et al. further teaches the amount of the component (B), relative to 100 parts by weight of the component (A) is preferably from 0.5 to 60 parts by weight, more preferably from 1 to 50 parts by weight, and still more preferably from 1 to 40 parts by weight [0689] (claims 8 and 9). Komuro et al. also teaches a specific example of photoreactive quencher (C) includes the following (C)-12:
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[0784] which is equivalent to a compound represented by formula (1) of instant claims 1 and 2, specifically formula (1-1) of instant claims 3 and 4 when n is 2, q is 0, m is 0, and Z+ is represented by formula (X-3) when Rc1 is a substituted, aromatic hydrocarbon having a carbon number of 6 and Rc2 and Rc3 are unsubstituted aromatic hydrocarbon groups having a carbon number of 6 having a pka of 1.30. Komuro et al. further teaches the amount of the component (C) relative to 100 parts by weight of the component (A) is preferably within a range from 0.5 to 10.0 parts by weight, more preferably from 0.5 to 8.0 parts by weight, still more preferably from 1.0 to 8.0 parts by weight, and particularly preferably from 1.5 to 5.5 parts by weight [0553], e.g. in Example 12, 8.26 parts by weight of (B)-1 and 1.34 parts by weight of (B)-2 and 3.08 parts by weight of (C)-12 were used such that the calculated mol% of compound (1), assuming parts by weight is grams, can be 30 mol% with respect to the acid generator (claim 10).
Komuro et al. does not teach a resin comprising a structural unit having an acid-dissociable group being represented by formula (5).
However, Namai teaches a radiation-sensitive resin composition includes a polymer that includes a structural unit represented by a formula (1), and an acid generator [0009] in which a specific example of formula (1) includes the following formula (M-7):
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[0241] which is the monomeric equivalent to a structural unit represented by formula (5) of instant claim 1 when R7 is a methyl group, L1 is a single bond, R8 is a hydrogen atom, and R9 and R10 taken together represent a divalent alicyclic unsaturated hydrocarbon group having 5 carbon atoms together with the carbon atom to which R9 and R10 are bonded. Namai also teaches when the polymer [A] includes the structural unit (I) that includes the above specific structure, the PEB temperature can be reduced, and a resist pattern can be formed with more excellent sensitivity, LWR performance, and resolution [0020].
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 Komuro et al. to further include a structural unit taught by Namai and arrive at the instant claims through routine experimentation in order to reduce PEB temperature and achieve excellent sensitivity, LWR, and resolution.
With regard to claims 13 and 14, Komuro et al. also the method of forming a resist pattern includes: forming a resist film on a substrate using the resist composition; conducting exposure of the resist film; and developing the resist film to form a resist pattern [0751] in which exposure is performed using an exposure apparatus such as an ArF exposure apparatus, a KrF exposure apparatus, an electron beam lithography apparatus or an EUV exposure apparatus, or by patterning via direct irradiation with an electron beam without using a mask pattern [0754].
Claims 21-24, 26, and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Komuro et al. (U.S. 2013/0224658).
Komuro et al. teaches a resist composition according to the present invention includes a base component (A) that exhibits changed solubility in a developing solution by the action of acid, a photoreactive quencher (C) and an acid generator component (B) which generates acid upon exposure [0032] in which in the case where the resist composition of the present invention is a resist composition which forms a positive pattern in an alkali developing process and a negative pattern in a solvent developing process, it is preferable to use a base component (A0) which exhibits increased polarity by the action of acid [0049] and the component (A0) may be a resin component (A1) that exhibits increased polarity under the action of acid, a low molecular weight material (A2) that exhibits increased polarity under the action of acid, or a mixture thereof [0053] wherein component (A1) preferably has a structural unit (a1) containing an acid decomposable group that exhibits increased polarity by the action of acid, a structural unit (a2) containing an --SO2-- containing cyclic group or a lactone-containing cyclic group, and a structural unit (a3) containing a polar group [0055-0057] and specific examples of the structural unit (a3) include structural units derived from (α-substituted) acrylic acid and structural units represented by general formulas (a3-11) to (a3-13) [0379] such as the following formula (a3-11-2):
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[0385] wherein R” is a hydrogen atom, a methyl group or a trifluoromethyl group [0385] which is equivalent to a resin comprising a structural unit having a phenolic hydroxyl group of instant claim 21. Komuro et al. further teaches a specific example of acid generator (B) includes the following (B)-4:
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[page 81] which is equivalent to a radiation-sensitive acid generator of instant claim 21 having a pka of -3.39 having a sulfonium cation represented by formula (X-3) when Rc1 and Rc2 are unsubstituted aromatic hydrocarbon groups having a carbon number of 6 and Rc3 is a substituted aromatic hydrocarbon group having a carbon number of 6. Komuro et al. further teaches a specific example of photoreactive quencher (C) includes the following (C)-12:
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[0784] which is equivalent to a compound represented by formula (1) of instant claims 21 and 22, specifically formula (1-1) of instant claims 23 and 24 when n is 2, q is 0, m is 0, and Z+ is represented by formula (X-3) when Rc1 is a substituted, aromatic hydrocarbon having a carbon number of 6 and Rc2 and Rc3 are unsubstituted aromatic hydrocarbon groups having a carbon number of 6 having a pka of 1.30. Komuro et al. further teaches the amount of the component (B), relative to 100 parts by weight of the component (A) is preferably from 0.5 to 60 parts by weight, more preferably from 1 to 50 parts by weight, and still more preferably from 1 to 40 parts by weight [0689] and the amount of the component (C) relative to 100 parts by weight of the component (A) is preferably within a range from 0.5 to 10.0 parts by weight, more preferably from 0.5 to 8.0 parts by weight, still more preferably from 1.0 to 8.0 parts by weight, and particularly preferably from 1.5 to 5.5 parts by weight [0553], e.g. in Example 12, 8.26 parts by weight of (B)-1 and 1.34 parts by weight of (B)-2 and 3.08 parts by weight of (C)-12 were used such that the calculated mol% of compound (1), assuming parts by weight is grams, can be 30 mol% with respect to the acid generator (claim 21). Komuro et al. also teaches while preferred embodiments of the invention have been described and illustrated, it should be understood that these are exemplary of the invention and are not to be considered as limiting. Additions, omissions, substitutions, and other modifications can be made without departing from the spirit or scope of the present invention. Accordingly, the invention is not to be considered as being limited by the foregoing description, and is only limited by the scope of the appended claims [0800] and an object of providing a resist composition which exhibits excellent lithography properties and has an excellent storage stability [0018].
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 Komuro et al. to include the above structural unit (a3-11-2) in the polymer and arrive at the instant claims through routine experimentation of combining equally suitable components for the sought invention in order to achieve excellent lithography properties and storage stability.
With regard to claims 26 and 27, Komuro et al. teaches the method of forming a resist pattern includes: forming a resist film on a substrate using the resist composition; conducting exposure of the resist film; and developing the resist film to form a resist pattern [0751] in which exposure is performed using an exposure apparatus such as an ArF exposure apparatus, a KrF exposure apparatus, an electron beam lithography apparatus or an EUV exposure apparatus, or by patterning via direct irradiation with an electron beam without using a mask pattern [0754].
Response to Arguments
Due to the amendment filed July 16, 2025 of instant claims 1 and 21, the 103 rejections over Takahashi as evidenced by Komuro in view of Namai, and Takahashi as evidenced by Komuro have been withdrawn. Applicant arguments with regard to these rejections have been considered but are moot due to the amendment of instant claims 1 and 21. However, Namai is still being used as prior art because it continues to teach claimed formula (5) and Komuro is still being used as prior art because it continues to teach the claimed composition.
Due to the amendment if instant claim 1, the objection has been withdrawn.
Due to the cancelation of instant claims 28 and 29, the 112(d) rejections have been withdrawn.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. U.S. 2020/0183273 and U.S. 2015/0309406.
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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/Anna Malloy/Examiner, Art Unit 1737 /JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734