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.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 05/25/2026, 03/03/2026, 10/24/2025, and 04/05/2024 are being considered by the examiner.
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 1-3 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.
Claim 1 recites that Rb1 is a fluorine atom or a fluorinated alkyl group and the corresponding subscript p01 is 1-5. Later in the claim, the reference states that at least one Rb1 is bonded to an ortho position or meta position of the benzene ring. Then, the reference states that the number of “all fluorine atoms contained in -F and/or CFRx1Rx2, which are bonded to an aromatic ring bonded to the sulfur atom in the formula is 3 or more, and Rx1 and Rx2 each independently represent a fluorine atom or a hydrogen atom”
The metes and bounds of this claim are difficult to determine – the recitation “all fluorine atoms contained in -F and/or CFRx1Rx2, which are bonded to an aromatic ring bonded to the sulfur atom in the formula is 3 or more” appears to be directed to Rb1, as that is the only recited group that may comprise fluorine(s). However - p01 is recited to be 1-5, and the further recitation then states “3 or more” with no definite endpoint (this endpoint is presumed to be 5, as there are no further substitutable carbons beyond 5). When Rb1 is a fluorine only (and not a fluoroalkyl group, this set of overlapping ranges renders the metes and bounds of the claims unclear.
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 "p01 is recited to be 1-5”, and the claim also recites “all fluorine atoms contained in -F and/or CFRx1Rx2, which are bonded to an aromatic ring bonded to the sulfur atom in the formula is 3 or more, and Rx1 and Rx2 each independently represent a fluorine atom or a hydrogen atom”, 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.
For the purposes of examination, the examiner will consider the broader statement to be controlling over claim scope as a matter of consideration over “Broadest Reasonable Interpretation”.
Further - the statement “all fluorine atoms contained in -F and/or CFRx1Rx2, which are bonded to an aromatic ring bonded to the sulfur atom in the formula is 3 or more, and Rx1 and Rx2 each independently represent a fluorine atom or a hydrogen atom” does not specify if the claimed “aromatic ring” is the benzene ring explicitly shown or may be an aromatic ring represented by Rb2 and/or Rb3. The wording of the claim language does not make it clear if “ all fluorine atoms… bonded to an aromatic ring… is 3 or more” refers to 1) there must be 2 or more fluorines on a single aryl group, 2) across any number of aryl rings in the sulfonium cation there must be 3 or more fluorines present, and/or 3) across any number of aryl rings in the sulfonium cation, each aryl ring must have 3 or more fluorines present.
For the purposes of examination, each and all of these interpretations are considered as the metes and bounds of this particular claim limitation are unclear.
As a matter of grammatical clarity, the examiner respectfully suggests that the claim be rewritten to further delineate portions referring to Rb2 and Rb3 more distinctly from those referring to Rb1.
Claims 2 and 3 are likewise rejected by nature of dependency because they carry the limitations of claim 1.
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)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(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.
Claim(s) 1-3 is/are rejected under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Hatakeyama et al (US 20210116808 A1, filed 10/02/2020, published 04/22/2021) as evidenced by a disclosure from EChemi.com( 2,3,5-triiodobenzoic acid Safety Data Sheet, Section 12 – Ecological Information).
Regarding Claim 1-3, Hatakeyama is directed to a composition comprising a base polymer having recurring units containing an imide group having an iodized aromatic ring bonded thereon and recurring units (b1) having an acid labile group substituted carboxyl group and/or recurring units (b) having an acid labile group-substituted phenolic hydroxyl group (Abstract).
The base resin (a) is generally disclosed from [0037] to [0099]. The composition also comprises an acid generator that is generally discussed from [0100]-[0140], where the acid generator functions to generate acid upon exposure to radiation, and this acid forces a solubility switch of the base resin by cleaving acid-labile groups thereon so as to change the solubility of the resin in a developer. Solvents used in the composition are discussed from [0141]-[0142].
A quencher - also called an acid diffusion control agent - may be included, where the reference generally discloses a quencher at [0142]-[0155], where preferably the quencher is a sulfonium salt of a nonfluorinated sulfonic acid or a carboxylic acid – these salts produce acids that are not strong enough to cleave/deprotect the acid-labile groups on the base resin.
In the experimental examples, Table 1 discloses Example 1, using base resin Polymer 1, photoacid generator PAG-1, and acid diffusion control agent Quencher Q-1:
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230
348
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376
334
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The resin of Example 1 meets the limitations of the claim for where:
The polymer (resin component A1) has a solubility in a developing solution that is changed by action of an acid (the acid labile imide and ester groups therein)
The resin composition generates acid upon exposure to light (acid generated by the photoacid generator PAG-1)
The quencher (acid diffusion control agent) meets the limitations of claimed compound (D) and (D0) where:
X0 is Iodine
Subscript nb1 is 3
Rm is H
Yd0 is a single bond
Rb1 is a fluorine
Subscript p01 is 1, and the substituent is in the meta-position on the phenyl ring
Rb2 and Rb3 are each phenyl rings (C6 hydrocarbon, specifically aryl, groups)
Hatakeyama does not explicitly disclose a pKa value for the quencher’s generated carboxylic acid . However - the disclosed compound anticipates the claimed formula and therefore should inherently possess the required pKa - if the composition is physically the same it should have the claimed property by nature of meeting the structural limitations of the claim, as properties are emergent from structure (See MPEP 2112.01.I. and .II).
However, the pKa value of the carboxylic acid generated from the quencher of Hatakeyama is approximately known - a Safety Data Sheet obtained from EChemi.com (See attached document, section 12) discloses that the pKa of 2,3,5-triiodobenzoic acid is approximately 1.5, meeting the limitations of the claim where the pKa of generated acid from the acid diffusion control agent is greater than 0.5.
Each resist composition tabulated in Table 1 was coated onto a silicon substrate having a spin-on silicon hard mask (claimed support) and then baked to form a resist film. After this, an EUV scanner was used to patternwise expose the resist to EUV radiation (extreme ultraviolet ray). After exposure, the resists were baked and then developed using TMAH developer (Claims 2 and 3) ([0206]).
Claim(s) 1-3 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Maruyama (US 20240004288 A1, filed 08/03/2021).
Regarding Claims 1-3, Maruyama discloses a radiation sensitive composition comprising one or two or more onium salts containing an organic cation moeity and an organic anion moeity, a compound having a structure in which an alkoxy-carbonyl group is bonded to a nitrogen atom, and a solvent (Abstract).
The composition of Maruyama is generally disclosed from [0036]-[0198], where the polymer resin comprising an acid labile group is generally discussed at [0070]-[0088] and acid generating agents are discussed from [0089]-[0100]. Acid diffusion controlling agents are discussed from [0101] to [0110].
Example 16 in the experimental examples comprises a polymer P-6, an acid generator PAG14, and a quencher/acid diffusion controlling agent Q-11:
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274
332
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594
366
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The resin of Example 16 meets the limitations of the claim for where:
The polymer (resin component A1) has a solubility in a developing solution that is changed by action of an acid (the acid labile ester groups therein)
The resin composition generates acid upon exposure to light (acid generated by the photoacid generator PAG14)
The quencher (acid diffusion control agent) Q-11 meets the limitations of claimed compound (D) and (D0) where:
X0 is Iodine
Subscript nb1 is 1
Rm is H
Yd0 is a divalent linking group (an oxymethylene group)
Rb1 is a fluorine
Subscript p01 is 2, and one fluorine substituent is in the meta-position on the phenyl ring
Rb2 and Rb3 are each phenyl rings (C6 hydrocarbon, specifically aryl, groups), where Rb2 is ortho substituted and meta substituted with F atoms, and Rb3 is ortho substituted
The total number of F atoms on an aromatic ring in the structure is 5.
Maruyama does not explicitly disclose a pKa value for the quencher’s generated carboxylic acid . However - the disclosed compound anticipates the claimed formula and therefore should inherently possess the required pKa - if the compound meets the limitations of the claim it should have the claimed property by nature of meeting the structural limitations of the claim, as properties are emergent from structure (See MPEP 2112.01.I. and .II).
Each resist composition tabulated in Table 1 was coated onto a silicon substrate having a spin-on silicon hard mask (claimed support) and then baked to form a resist film. After this, an EUV scanner was used to patternwise expose the resist to EUV radiation (extreme ultraviolet ray). After exposure, the resists were baked and then developed using TMAH developer ([0219]) (Claims 2 and 3).
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sally Merkling can be reached at 571-272-6297. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/A.P.T./Examiner, Art Unit 1737
/SALLY A MERKLING/SPE, Art Unit 1738
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