DETAILED ACTION
Claims 1, 3, 5, 7, 8, 10, 11, and 13-22 are pending. Claims 1, 3, and 15 have been amended and claims 2, 4, 6, 9, and 12 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 .
Priority
Acknowledgment is made of applicant's claim for foreign priority based on an application filed in Japan on February 8, 2023. It is noted, however, that applicant has not filed a certified copy of the JP2023-017434 application as required by 37 CFR 1.55.
Specification
The disclosure is objected to because of the following informalities: Regarding formula (1’), pages 6 and 13 recite ‘”m” and “n” each represent 1 or 2’ but also recites that “R1’ represents a hydrogen atom…”. It is generally understood for a compound having substituents that a hydrogen atom is being replaced by said substituent. However, this cannot be assumed for formula (1’) since -R1’ can be hydrogen and the number of substituents does not add up to the number of available carbon atoms, e.g. when R1’ is a hydrogen atom, n is 1, and m is 1, it is unclear what is present on the remaining two carbon atoms of the phenyl ring. That is, if the definition of the “substituent” includes hydrogen, the number of substituents must correspond to the number of available carbon atoms, in this case 3 or 4 since m is 1 or 2. Based on page 23 which depicts compounds having only one substituent -OCHpFq, the Examiner suggests amending n to represent 3 or 4 for formula (1’) only.
Appropriate correction is required.
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.
Claim 3 is 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 3 recites formula (1’) in which ‘ “m” and “n” each represent 1 or 2’ while “R1’ represents a hydrogen atom”. It is generally understood for a compound having substituents that a hydrogen atom is being replaced by said substituent. However, this cannot be assumed for formula (1’) since -R1’ can be hydrogen and the number of substituents does not add up to the number of available carbon atoms, e.g. when R1’ is a hydrogen atom, n is 1, and m is 1, it is unclear what is present on the remaining two carbon atoms of the phenyl ring. That is, if the definition of the “substituent” includes hydrogen, the number of substituents must correspond to the number of available carbon atoms, in this case 3 or 4 since m is 1 or 2. The Examiner suggests, based on the compounds shown on page 23, amending n to represent 3 or 4.
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, 3, 5, 7, 8, 10, 11, 13-16, and 19-22 are rejected under 35 U.S.C. 103 as being unpatentable over Hoshiko et al. (JP2016085382). Translation attached.
Hoshiko et al. teaches a chemically amplified radiation-sensitive resin composition containing a polymer having a structural unit containing an acid-dissociable group ((A) polymer), a radiation-sensitive acid generator (B), an acid diffusion control agent (C), and solvent (D) [0024] (claims 1, 5, 8, 10, 11, 13, 14, and 16) wherein the acid diffusion control agent (C) can be an onium salt compound and examples include a sulfonium salt compound represented by the following formula (4) [0092]:
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[0093] wherein R22 to R24 can be hydrogen and Z- can be an anion represented by the following formula (6) [0094]:
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[0095] wherein u can be 1 and R28 can be a linear alkoxy group having 1 carbon atom in which all of the hydrogen atoms are substituted with a halogen atom [0096] which is equivalent to a sulfonium salt of an unsubstituted hydroxy(trifluoromethoxy)benzoic acid represented by formula (1) of instant claim 1 when m is 1, X is an oxygen atom, n is 1, R1 is a hydrogen atom, and R2-R4 are hydrocarbyl groups having 6 carbon atoms and equivalent to an unsubstituted hydroxy(trifluoromethoxy)benzoic acid represented by formula (1) of instant claim 3 when m is 1, X is an oxygen atom, p is 0, q is 3, n is 1, R1’ is a hydroxy group, and R2-R4 are hydrocarbyl groups having 6 carbon atoms. Hoshiko et al. also teaches the present invention will be specifically described based on Examples, but the present invention is not limited to these Examples [0113] and it is possible to provide a novel resist pattern-forming method capable of forming a pattern in which NOK and LWR are suppressed, and having sufficiently satisfactory sensitivity, and a radiation-sensitive resin composition used in the resist pattern-forming method [0144].
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 Hoshiko et al. to include additional compositions comprising the above defined acid diffusion control agent (C) and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention in order to achieve optimum suppression of NOK and LWR as well as optimum sensitivity.
With regard to claim 7, Hoshiko et al. teaches the radiation-sensitive acid generator (B) include onium salts, N-sulfonyloxy imido compounds, halogen-containing compounds, and diazoketone compounds [0078] and examples of the onium salt compound includes a sulfonium salt [0079] and examples of the sulfonium salt includes triphenylsulfonium trifluoromethanesulfonate [0080] which is equivalent to an acid generator which generates a sulfonic acid of instant claim 7.
With regard to claim 15, Hoshiko et al. teaches examples of the structural unit contained in polymer (A) include at least one structural unit (X) selected from a structural unit (I) having a group that is dissociated by the action of an acid, a structural unit (II) having a group in which at least one of hydrogen atoms on an aromatic ring is substituted with a hydroxyl group, a structural unit (XI) having a hydrocarbyl group substituted with at least one selected from an alcoholic hydroxyl group, a carboxyl group, a cyano, and a sulfo (including a group that generates a sulfo by the action of an acid), and a structural unit (X2) having at least one structural unit selected from a lactone structure, a cyclic carbonate structure, and a sultone structure [0030] and structural unit (I) is preferably at least one selected from a structural unit (P-1) represented by formula (p-1), a structural unit (P-II) represented by formula (p-2), and a structural unit (P-III) derived from an acetalized hydroxystyrene [0031] in which examples of formula (p-1) include the following formula (p-1-1) [0039]:
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[0040] wherein R14 is hydrogen, fluoro, methyl, trifluoromethyl or hydroxy methyl [0034] and R15 is a linear or branched alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 22 carbon atoms [0041] which is equivalent to a base polymer comprising a repeating unit represented by general formula (a1) of instant claim 15 when RA is a hydrogen atom or a methyl group, Y1 is a single bond, and R11 is an acid-labile group.
With regard to claim 19, Hoshiko et al. teaches structural unit (XI) having a hydrocarbyl group substituted with at least one selected from an alcoholic hydroxyl group, a carboxyl group, a cyano, and a sulfo includes a group that generates a sulfo by the action of an acid [0054] such as the following formula (C-7-23) [0060]:
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[0060] which is equivalent to formula (f3) of instant claim 19 when RA is a hydrogen atom, Z5 is a phenylene group, and R26-R28 are hydrocarbyl groups having 6 carbon atoms.
With regard to claim 20, Hoshiko et al teaches the radiation-sensitive resin composition may contain, as other components, a surfactant [0108].
With regard to claims 21 and 22, Hoshiko et al. teaches on a 12-inch silicon wafer having an underlayer film formed thereon, a resist film having a thickness of 50nm was formed using the photoresist composition, and PB was performed at a temperature shown in Table 3 for 60 seconds. Next, using an EUV exposure device, exposure was performed through a mask. After the exposure, each photoresist composition was subjected to PEB at a temperatures shown in Table 3 for 60 seconds. Thereafter, the resist film was developed with a 2.38% by mass aqueous tetramethylammonium hydroxide solution, washed with water, washed with an aqueous washing solution, and dried to form a positive resist pattern [0135].
Claims 1, 3, 5, 7, 8, 10, 11, 13-18, and 20-22 are rejected under 35 U.S.C. 103 as being unpatentable over Oono et al. (U.S. 6,723,483).
Oono et al. teaches a compound which is shown by following general formula [3]:
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[col 2 line 50] wherein X is a phenyl group which has a substituent at an ortho- and/or a meta-position, m is an integer of 1 to 3, q is an integer of 0 to 2, provided that m+q=3, p is an integer of 1 or 2 and Zp- is an anion derived from a carboxylic acid [col 2 lines 57-60] and an anion originated from a carboxylic acid, shown by Zp-, includes one derived by a carboxylic acid shown by the general formula [4] [col 5 lines 48-50]:
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[col 5 line 51] wherein R5 is a hydrogen atom or a monovalent hydrocarbon residue which may have a substituent [col 5 line 54-55]. Oono et al. also teaches in the general formula [4], a hydrocarbon residue in a monovalent hydrocarbon residue which may have a substituent, shown by R5 includes an aliphatic hydrocarbon group, an aromatic hydrocarbon group and an aromatic aliphatic hydrocarbon group and the residue may have a sulfur atom in its chain [col 5 lines 62-67], the aromatic hydrocarbon group includes an aryl group, etc. The aryl group includes one having generally 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms, which is specifically exemplified by a phenyl group [col 6 lines 49-52] and the substituent in the monovalent hydrocarbon residue which may have a substituent, shown by R5 includes a hydroxy group and a lower alkoxy group such as a methoxy group and particularly a group having an electron-accepting such as a halogen atom is preferable (i.e. a trifluoromethoxy group) [col 5 line 64-col 7 line 65] and examples include halogenated alkoxy aromatic monocarboxylic acids such as trifluoromethoxybenzoic acid [col 7 lines 64-65] and hydroxy aromatic monocarboxylic acids such as salicylic acid [col 8 lines 6-7] such that when R5 is a phenyl group substituted by both a hydroxy group and a halogenated alkoxy group (i.e. trifluoromethoxy) it is equivalent to a sulfonium salt of an unsubstituted hydroxy(trifluoromethoxy)benzoic acid represented by formula (1) of instant claim 1 when m is 1, X is an oxygen atom, n is 1, R1 is a hydrogen atom, and R2-R4 are hydrocarbyl groups having 6 carbon atoms and equivalent to an unsubstituted hydroxy(trifluoromethoxy)benzoic acid represented by formula (1) of instant claim 3 when m is 1, X is an oxygen atom, p is 0, q is 3, n is 1, R1’ is a hydroxy group, R2 is a hydrocarbyl group having at least 6 carbon atoms and having a heteroatom, and R3 and R4 are hydrocarbyl groups having 6 carbon atoms. Oono et al. also teaches the present invention is explained in detail referring to examples, but the present invention is not limited thereto by any means [col 25 lines 40-42] and the sulfonium salt compound of the present invention can generate an acid by irradiation with UV, deep UV, KrF excimer laser, ArF excimer laser, F2 excimer laser, electron beams, X-ray or actinic rays, and therefore the sulfonium salt can be used as an acid generator, which can form a good pattern without being accompanied with drawback such as formation of fine particles during storage, which is observed in case of use of known acid generator, Further, the sulfonium salt compound is useful as an acid generator for resists and also useful as a cationic photo polymerization initiator [col 44 lines 38-47].
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 Oono et al. to include additional compounds comprising the above defined salt and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention in order to achieve a good pattern without being accompanied with drawback such as formation of fine particles during storage.
With regard to claims 5, 8, 10, 11, 13-18, and 20, Oono et al. teaches the chemically amplified positive tone resists to which the sulfonium salt of the present invention is applied are roughly classified into two component type resists and three component type resists [col 13 lines 52-55] and the three component type resists comprise one or more kinds of polymers (or resins) soluble in an alkaline developing solution, one or more kinds of dissolving-inhibiting agents containing as pending groups protecting groups which become soluble in an alkaline developing solution by an act of an acid, one or more kinds of the sulfonium salts of the present invention, if necessary, one or more kinds of acid generators except the above sulfonium salts, such as ones shown by general formula [8], and, upon necessity, basic compounds, acidic compounds, UV-absorbers, surfactants, and solvents dissolving those components. On the other hand, the chemically amplified negative tone resists of the present invention in which the sulfonium salts of the present invention are used comprise one or more kinds of polymers (or resins) soluble in an alkaline developing solution, cross-linking agents which cross-link polymers by heating in the presence of an acid so as to make the polymers insoluble in an alkaline developing solution, one or more kinds of the sulfonium salts of the present invention, if necessary, one or more kinds of acid generators except the above sulfonium salts, such as ones shown by general formula [8], and, upon necessity, basic compounds, acidic compounds, UV-absorbers, surfactants and solvents dissolving those components [col 13 line 66-col 14 line 21]. Oono et al. also teaches The polymers (or resins) containing as pending group protecting groups which become soluble in an alkaline developing solution by an act of an acid include those shown by the following general formula [9] [col 14 lines 2-25]:
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[col 14 line 30] wherein R11, R12, R13 and R14 are each independently a hydrogen atom or a methyl group, R15 is a hydrogen atom or a lower alkyl group, R16 is a lower alkyl group, and R15 and R16 may form an alicyclic ring together with a carbon atom to which they are bound, R17 is an alkyl group or an aralkyl group, R18 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a tetrahydropyranyloxy group, a tetrahydrofuranyloxy group, a tert-butoxycarbonyloxy group, a tert-amyloxycarbonyloxy group, a benzoyloxy group, an acetyloxy group, a pivaloyloxy group or a tert-butoxycarbonylmethyloxy group, R19 is a hydrogen atom or a cyano group, R20 is a cyano group or a carboxyl group which may be esterified, r, e and g are 0 or a natural number and t is a natural number, providing that 0≤r/r+t+e+g≤0.5, 0≤e/r+t+e+g≤0.3, 0≤g/r+t+e+g≤0.3 and 0.2<r+e+g/r+t+e+g≤0.8 [col 14 lines 40-55] in which t is equivalent to a repeating unit represented by general formula (a2) of instant claim 15 when RA is a hydrogen atom or a methyl group, Y2 is a single bond, R14 is a single bond, Y3 is a single bond, b is 0, and a is 1 where R12 is an acid-labile group.
With regard to claim 7, Oono et al. teaches sulfonium salt compounds which can be used more practically as an acid generator for a resist and as a cationic type photo polymerization initiator [col 2 lines 16-18] specifically, a compound of general formula [1] [col 2 line 21] in which the preferable specific examples of the compound shown by the general formula [1] are diphenyl-o-methylphenylsulfonium p-toluenesulfonate [col 4 lines 28-30] which is equivalent to an acid generator generating a sulfonic acid of instant claim 7.
With regard to claims 21 and 22, Oono et al. teaches a method for formation of a pattern comprising (i) a process of coating the above resist composition on a substrate, (ii) a process of irradiating, after heating, a light having a wavelength of 220 nm or less on the substrate through a mask, and (iii) a process of developing using a developing solution, after heat treatment, if necessary [col 3 lines 1-8].
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Oono et al. (U.S. 6,723,483) as applied to claim 11 above, and further in view of Matsumaru et al. (U.S. 2007/0231708).
With regard to claim 19, Oono et al. teaches the above polymer of general formula [9].
Oono et al. does not teach a repeating unit represented by general formulae (f1) to (f3).
However, Matsumaru et al. teaches a polymer compound capable of forming a positive resist composition that can form a high-resolution pattern with a reduced level of LER, an acid generator formed from such a polymer compound, a positive resist composition that includes such a polymer compound, and a method for forming a resist pattern that uses such a positive resist composition. The polymer compound includes a structural unit (a1) derived from an (α-lower alkyl) acrylate ester having an acid-dissociable, dissolution-inhibiting group, a structural unit (a2) represented by a general formula (a2-1) shown below [wherein, R represents a hydrogen atom or a lower alkyl group; A represents a divalent organic group; B represents a monovalent organic group; X represents a sulfur atom or iodine atom; n represents either 1 or 2; and Y represents a straight-chain, branched or cyclic alkyl group in which at least one hydrogen atom may be substituted with a fluorine atom], and a structural unit (a3) derived from an (α-lower alkyl) acrylate ester that contains a polar group-containing aliphatic polycyclic group [abstract]:
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[abstract] and a specific example includes the following monomer (1):
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[0149] which, when polymerized, is equivalent to general formula (f1) of instant claim 19 when Z2 is -C(=O)-O-Z11- where Z11 is a phenylene group, R21 and R22 are hydrocarbyl groups having 6 carbon atoms, and M- is a non-nucleophilic counterion.
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 Oono et al. to include additional repeating units such as those taught by Matsumaru et al. and arrive at the instant claims through routine experimentation of combining equally suitable components for the sought invention in order to achieve a high-resolution pattern with a reduced level of LER.
Response to Arguments
Due to the amendment filed June 16, 2026 of instant claims 1 and 3, the 102(a)(1) rejection over Tsuchimura and the 103 rejection over Hatakeyama. Applicant’s arguments with regard to these rejections have been considered but are moot due to the amendment of instant claims 1 and 3.
Applicant’s arguments with respect to the objection to the specification and 112(d) rejection of instants 2 and 4 regarding the naming of the inventive compounds have been fully considered and are persuasive. Some of the objections of the specification have been withdrawn. Due to the cancelation of claims 2 and 4, the 112(d) rejections have been withdrawn.
However, the objection to the specification regarding the definition of n for formula (1’) is maintained, see objection above.
Due to the cancelation of instant claim 4, the 112(b) rejection has been withdrawn. However, the issue is now present in instant claim 3. Specifically, the definition of “n” together with the definition of R1’ is unclear, see rejection above.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. U.S. 2022/0283498.
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.
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Keith Walker can be reached at 571-272-3458. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Anna Malloy/ Examiner, Art Unit 1737
/KEITH WALKER/ Supervisory Patent Examiner, Art Unit 1735
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