DETAILED ACTION
Claims 1-15 are pending. Claim 15 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 .
Response to Arguments
Applicant’s arguments filed February 27, 2026, with respect to the rejection(s) of claim(s) 1-14 under 103 over Thackeray in view of Hatakeyama and Nakamura have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of newly found prior art Kim et al. (U.S. 2023/0131429), Oka et al. (WO2021199789), and/or Okuaki et al. (U.S. 2023/0259029).
Therefore, this action is Non-Final.
Terminal Disclaimer
The terminal disclaimer filed on February 19, 2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of copending application 18/095,221 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Claim Objections
Claims 1 and 15 are objected to because of the following informalities: Claim 1 recites “is case of s=1, two groups R8 may be…” but should instead recite --R4--. Claim 15 recites
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in lines 11 and 15; in line 12,
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in which the right two anions are duplicates of the left anion and also recites
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in line 28; recites
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in lines 13 and 27; recites
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in lines 14 and 28; recites
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in line 24 in which the leftmost and rightmost are the same; and recites
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in lines 59 and 71. The duplicates should be omitted. Claim 15 also has two blank pages, pages 21 and 23. Claim 15 is also missing a period. Appropriate correction is required.
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 § 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, 5-10, and 12-15 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (U.S. 2023/0131429).
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.
Kim et al. teaches a photo-decomposable compound according to embodiments may include, e.g., a phenyl sulfonium cation component (which may be used interchangeably with the term ‘cation component’ herein) and an anion component. The phenyl sulfonium cation component may have a protecting group, which may decompose by an action of acid during or in response to exposure and may generate an alkali-soluble group, and the anion component may generate acid due or in response to exposure [0013] e.g. represented by Formula 1 [0018]:
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[0018] m1 and m2 may be 0 [0021], Ya may be an unsubstituted C1 to C30 divalent linear group [0022], X- may be a monovalent anion [0023], and R1 may be the following structure:
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[0026] and in an implementation, the photo-decomposable compound may act as a photo-decomposable quencher (PDQ), which generates a relatively weak acid in the photoresist composition due to exposure and neutralizes acid before exposure. In an implementation, in Formulae 1, 1-1, 1-2, and 1-3, X− may have, e.g., one of the following structures [0056]:
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[0056] which is equivalent to a sulfonium salt having the formula (1) of instant claims 1-3 and 15 when s is 1, r is 1, R1 is an ether bond, R2 is a C1-C20 alkanediyl group, RAL is represented by formula (AL-1) when R5 is hydrogen, Ra1 is a C2 tetravalent saturated hydrocarbon group, m1 is 0, n1 is 0, p is 0, q is 0, R4 is a C6 hydrocarbyl group, and X- is a carboxylate anion of instant claim 2, specifically of formula (2)-1 of instant claim 3, more specifically the appropriate anions shown in claim 15. Kim et al. also teaches the photoresist composition according to the embodiments may include a chemically amplified polymer, a photo-decomposable compound, and a solvent [0060] (claims 7 and 8), the chemically amplified polymer may include positive-type photoresist [0062] (claim 10), and the chemically amplified polymer may have a structure in which the first repeating unit derived from hydroxystyrene or the hydroxystyrene derivative is copolymerized with at least one second repeating unit having an acid-labile protecting group. The at least one second repeating unit may include a (meth)acrylate polymer. In an implementation, the at least one second repeating unit may include polymethylmethacrylate (PMMA), poly(t-butylmethacrylate), poly(methacrylic acid), poly(norbornylmethacrylate), or a binary or ternary copolymer of repeating units of the (meth)acrylate-based polymers [0064] and the acid-labile group, which may be included in the at least one second repeating unit, may include, e.g., tert-butoxycarbonyl (t-BOC), isonorbornyl, 2-methyl-2-adamantyl, 2-ethyl-2-adamantyl, 3-tetrahydrofuranyl, 3-oxocyclohexyl, γ-butyllactone-3-yl, mavaloniclactone, γ-butyrolactone-2-yl, 3-methyl-γ-butyrolactone-3-yl, 2-tetrahydropyranyl, 2-tetrahydrofuranyl, 2,3-propylenecarbonate yl, 1-methoxyethyl, 1-ethoxyethyl, 1-(2-methoxyethoxy)ethyl, 1-(2-acetoxyethoxy)ethyl, t-buthoxycarbonylmethyl, methoxymethyl, ethoxymethyl, trimethoxysilyl, or a triethoxysilyl group [0066] such that t-butylmethacrylate is equivalent to a repeat unit having the formula (a1) of instant claim 9 when R is methyl, X1 is a single bond, and R21 is an acid labile group. Kim et al. further teaches the photo-decomposable compound included in the photoresist composition may act as a PAG capable of generating acid or a PDQ capable of neutralizing acid, depending on a type of the anion component included in the photo-decomposable compound. In an implementation, the photoresist composition according to the embodiments may further include an additional PAG configured to generate acids due to exposure. The additional PAG may include a material having a different chemical structural formula from that of the photo-decomposable compound. In an implementation, the additional PAG may generate acid when exposed to any one of a KrF excimer laser (248 nm), an ArF excimer laser (193 nm), an F.sub.2 excimer laser (157 nm), and an EUV laser (13.5 nm). The PAG may include a material that generates a relatively strong acid having a pKa of about −20 or more and less than about 1 due to exposure. The PAG may include, e.g., triarylsulfonium salts, diaryliodonium salts, sulfonates, or a mixture thereof. For example, the PAG may include triphenyl sulfonium triflate, triphenyl sulfonium antimonate, diphenyliodonium triflate, diphenyliodonium antimonate, methoxydiphenyliodonium triflate, di-t-butyldiphenyliodonium triflate, 2,6-dinitrobenzyl sulfonates, pyrogallol tris(alkylsulfonates), N-hydroxysuccinimide triflate, norbornene-dicarboximide-triflate, triphenyl sulfonium nonaflate, diphenyliodonium nonaflate, methoxydiphenyliodonium nonaflate, di-t-butyldiphenyliodonium nonaflate, N-hydroxysuccinimide nonaflate, norbornene-dicarboximide-nonaflate, triphenyl sulfonium perfluorobutanesulfonate, triphenyl sulfonium perfluorooctanesulfonate (PFOS), diphenyliodonium PFOS, methoxydiphenyliodonium PFOS, di-t-butyldiphenyliodonium triflate, N-hydroxysuccinimide PFOS, norbornene-dicarboximide PFOS, or a mixture thereof [0069-0071] (claims 5 and 6). Kim et al. also teaches the photoresist composition according to the embodiments may further include a surfactant [0080] (claim 12). Kim et al. further teaches a method of manufacturing an integrated circuit (IC) device, the method including forming a photoresist film on a underlayer film by using a photoresist composition that includes a chemically amplified polymer, a photo-decomposable compound, and a solvent, the photo-decomposable compound including a phenyl sulfonium cation component and an anion component, the phenyl sulfonium cation component having a protecting group that is decomposable by an action of acid in response to exposure and generates an alkali-soluble group in response to exposure, and the anion component generating acid in response to exposure, the protecting group being represented by *—C(═O)OR, in which R is a substituted or unsubstituted t-butyl group or a substituted or unsubstituted C3 to C30 alicyclic group, and * is a bonding site, and the protecting group being bonded to a phenyl group of the phenyl sulfonium cation component through an ether linking group, exposing a first area, which is a portion of the photoresist film, to generate acid from the anion component of the photo-decomposable compound, deprotect an acid-labile group included in the chemically amplified polymer, and generate an alkali-soluble group from the phenyl sulfonium cation component of the photo-decomposable compound in the first area; removing the exposed first area of the photoresist film and the alkali-soluble group using a developer to form a photoresist pattern, the photoresist pattern comprising a non-exposed area of the photoresist film, and processing the underlayer film using the photoresist pattern [0007] in which an EUV lithography technique may include an exposure process using EUV light having a wavelength of about 13.5 nm as an advanced technique [0085] (claims 13 and 14). Kim et al. also teaches example embodiments have been disclosed herein, and although specific terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent to one of ordinary skill in the art as of the filing of the present application, features, characteristics, and/or elements described in connection with a particular embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of skill in the art that various changes in form and details may be made without departing from the spirit and scope of the present invention as set forth in the following claims [0153].
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 Kim et al. and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention with a reasonable expectation of success.
Claims 1-15 are rejected under 35 U.S.C. 103 as being unpatentable over Okuaki et al. (U.S. 2023/0259029).
Okuaki et al. teaches the actinic ray-sensitive or radiation-sensitive resin composition of an embodiment of the present invention (hereinafter also referred to as a “resist composition”) includes: a resin of which polarity increases through decomposition by the action of an acid (hereinafter also referred to as an “acid-decomposable resin” or a “resin (A)”, and a compound that generates an acid upon irradiation with actinic rays or radiation (hereinafter also referred to as a “photoacid generator”), in which the resin includes a resin (hereinafter also referred to as a “specific acid-decomposable resin”) containing a repeating unit X1 having two or more groups of which polarity increases through decomposition by the action of an acid (hereinafter also referred to as “acid-decomposable groups”) and a repeating unit X2 having a phenolic hydroxyl group (hereinafter also referred to as an “acid-decomposable group”) [0053-0056] and the resist composition may be either a positive tone resist composition or a negative tone resist composition [0063] (claims 5, 8, and 10). Okuaki et al. also teaches the specific acid-decomposable resin may include another repeating unit other than the above-mentioned repeating units. Examples of such another repeating unit include a repeating unit having an acid-decomposable group other than the above-mentioned repeating unit X1 [0193-0194] and a specific example includes the following:
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[0227] wherein Xa1 represents H, CH3, CF3, or CH2OH and Rxa represents a linear or branched alkyl group having 1 to 5 carbon atoms [0227] which is equivalent to a repeat unit having a formula (a1) of instant claim 9 when RA is hydrogen or methyl, X1 is a single bond, and R21 is an acid labile group. Okuaki et al. further teaches the specific acid-decomposable resin may have, as a repeating unit other than those above, a repeating unit having a group that generates an acid upon irradiation with actinic rays or radiation (hereinafter also referred to as a “photoacid generating group”) [0318] such as the following:
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[0322] which is equivalent to a repeat unit having a formula (f3) of instant claim 11 when RA is methyl, Z5 is -C(=O)-O-Z51- where Z51 is a C3 hydrocarbylene group, and R36-R38 are C6 hydrocarbyl groups and a pair bond together to form a ring. Okuaki et al. also teaches the resist composition may include an acid diffusion control agent as a component different from the above-mentioned components [0631] and as the acid diffusion control agent, an onium salt which serves as a weak acid relative to the photoacid generating component can also be used [0633] and as the onium salt which serves as a relatively weak acid with respect to the photoacid generating component, compounds represented by Formulae (d1-1) to (d1-3) are preferable [0635]:
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[0635] wherein R51 is an organic group. R51 preferably has 1 to 30 carbon atoms [0636], Z2c is an organic group. The organic group preferably has 1 to 30 carbon atoms [0637], R52 is an organic group (an alkyl group and the like), Y3 is —SO2—, a linear, branched, or cyclic alkylene group, or an arylene group, Y4 is —CO— or —SO2—, and Rf is a hydrocarbon group having a fluorine atom (a fluoroalkyl group and the like) [0638] such as the following anion for acid diffusion control agent D-8:
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[0750], and M+'s are each independently an ammonium cation, a sulfonium cation, or an iodonium cation. These cations may have an acid-decomposable group. As M+ in Formulae (d1-1) to (d1-3), the cations mentioned in the description of the specific photoacid generators and another photoacid generator may be used [0638-0639] wherein the organic cations represented by M11+ and M12+ are each independently preferably an organic cation represented by Formula (ZaI) (cation (ZaI)) or an organic cation represented by Formula (ZaII) (cation (ZaII)) [0464] where (ZaI) is the following:
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[0464] wherein R201, R202, and R203 each independently represent an organic group. The organic group as each of R201, R202, and R203 usually has 1 to 30 carbon atoms, and preferably has 1 to 20 carbon atoms [0466-0467], the cation (ZaI-1) is an arylsulfonium cation in which at least one of R201, R202, or R203 of Formula (ZaI) is an aryl group [0470] and examples of the arylsulfonium cation include a triarylsulfonium cation [0473] and as the aryl group included in the arylsulfonium cation, a phenyl group or a naphthyl group is preferable, and the phenyl group is more preferable [0474] and it is also preferable that the substituents form an acid-decomposable group by any combination. Furthermore, the acid-decomposable group is intended to be a group that decomposes by the action of an acid to produce an acid group, and preferably has a structure in which an acid group is protected by a leaving group that leaves by the action of an acid. The acid group and the leaving group are as described above [0478-0479] such as an acid-decomposable group associated with a repeating unit represented by Formula (B) [0228], e.g. the following -COO-CH3-indane group attached to a styrene repeating unit:
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[page 24] and in a case where each of the groups in Formula (B) has a substituent, examples of the substituent include an alkyl group (having 1 to 4 carbon atoms), a halogen atom, a hydroxyl group, an alkoxy group (having 1 to 4 carbon atoms), a carboxyl group, and an alkoxycarbonyl group (having 2 to 6 carbon atoms) such that when acid diffusion control agent of formula (d1-1) when R51 is a hydroxy substituted C6 phenyl and M+ is a triphenylsulfonium substituted with an acid-decomposable group such as -COO-CH3-indane it is equivalent to a sulfonium salt having the formula (1) of instant claims 1-4 and 15 when s is 1, r is 1, R1 is an ether bond, R2 is a C1-C20 alkanediyl group, RAL is represented by formula (AL-1) when R5 is hydrogen, Ra1 is a C2 tetravalent saturated hydrocarbon group, m1 is 0 or 1 where R6 can be fluorine, iodine, optionally fluorinated C1-C4 alkyl group, or optionally fluorinated C1-C4 alkoxy group, n1 is 0, p is 0, q is 0, R4 is a C6 hydrocarbyl group, and X- is a carboxylate anion of instant claim 2, specifically of formula (2)-1 of instant claim 3, more specifically the left anion in line 23 of instant claim 15. Okuaki et al. further teaches an example of the photoacid generator includes the following B-1:
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[-0748] which is equivalent to an acid generator capable of generating a strong sulfonic acid and fluorinated imide acid of instant claims 5 and 6. Okuaki et al. also teaches the resist composition may include a surfactant [0654] and a solvent [0660] (claims 7 and 12). Okuaki et al. further teaches the procedure of the pattern forming method using the resist composition is not particularly limited, but preferably has the following steps. Step 1: A step of forming a resist film on a substrate, using a resist composition; Step 2: A step of exposing the resist film; Step 3: A step of developing the exposed resist film using a developer [0679-0682] in which examples of the exposing method include a method of irradiating the resist film formed with actinic rays or radiation through a predetermined mask. Examples of the actinic rays or radiation include infrared light, visible light, ultraviolet light, far ultraviolet light, extreme ultraviolet light, X-rays, and electron beams, preferably a far ultraviolet light having a wavelength of 250 nm or less, more preferably a far ultraviolet light having a wavelength of 220 nm or less, and particularly preferably a far ultraviolet light having a wavelength of 1 to 200 nm, specifically, KrF excimer laser (248 nm), ArF excimer laser (193 nm), F2 excimer laser (157 nm), EUV (13 nm), X-rays, and electron beams [0699-0700] (claims 13 and 14). Okuaki et al. also teaches the present invention will be described in more detail with reference to Examples. The materials, the amounts of materials used, the proportions, the treatment details, the treatment procedure, and the like shown in Examples below may be appropriately modified as long as the modifications do not depart from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited to Examples shown below [0735] and an object of the present invention is to provide an actinic ray-sensitive or radiation-sensitive resin composition having an excellent resolution [0008].
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 Okuaki et al. and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention in order to achieve optimum resolution.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. WO2021199789 (U.S. 2023/0087940).
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark Huff can be reached at 571-272-1385. 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
/MARK F. HUFF/Supervisory Patent Examiner, Art Unit 1737
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