DETAILED ACTION
Claims 1, 5-7, 10, 13, and 15-18 are pending. Claims 1 and 10 have been amended, claims 3, 4, 8, and 9 have been canceled, and claims 2, 11, 12, 14, 19, and 20 were previously 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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 December 15, 2025 has been entered.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 5-7 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 5 recites “The resist composition of claim 1 wherein M+ is a cation…”. However, claim 1 does not recite M+. Thus, claim 5 fails to include all of the limitations of claim 1 as well as fail to further limit the subject matter of claim 1. Claim 6 recites “The resist composition of claim 5, having the following formula (3) or (4)”. However, formula (3) and (4) are broader formulae of formulae Q-1 and Q-2 recited in claim 1. Thus, claim 6 fails to further limit the subject matter of claims 1 and 5. Claim 7 recites “The resist composition of claim 1 wherein n is 2 or 3”. However, claim 1 does not recite n. Thus, claim 7 fails to include all of the limitations of claim 1 as well as fail to further limit the subject matter of claim 1. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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, 5-7, 10, 13, and 15-18 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (U.S. 2017/0351177) in view of Domon et al. (U.S. 2015/0253664).
Hatakeyama et al. teaches a resist composition comprising a base polymer and a sulfonium salt of iodized benzoic acid [0045] and when the resist composition is of positive tone, the base polymer comprises recurring units containing an acid labile group, preferably recurring units having the formula (a1) or recurring units having the formula (a2) [0062], the base polymer may further comprise recurring units (b) having a phenolic hydroxyl group as an adhesive group [0069], and in a further embodiment, recurring units (f) derived from an onium salt having polymerizable olefin may be incorporated in the base polymer. As discussed in Hatakeyama et al., JP-A 2005-084365 discloses sulfonium and iodonium salts having polymerizable olefin capable of generating a sulfonic acid. As also discussed in Hatakeyama et al., JP-A 2006-178317 discloses a sulfonium salt having sulfonic acid directly attached to the main chain [0074] in which a specific example includes the following Polymer 6:
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[0144] which is equivalent to a base polymer of instant claims 1, 10, and 13 comprising a recurring unit having the formula (a) when RA is a hydrogen, XA is a single bond, and AL1 is an acid labile group having the formula (L1) where a is 1 and R11 is a C1 hydrocarbyl group; a recurring unit having the formula (d2) when RB is methyl, n1 is 1, ZB is a C10 hydrocarbylene group, RHF is trifluoromethyl, R33 is a C6 hydrocarbyl group, and R34 and R35 are C6 hydrocarbyl groups which are bonded to form a ring with the sulfur atom to which they are attached; and a recurring unit having the formula (c) when RA is hydrogen, YA is a single bond, b is 1, and c is 0. Hatakeyama et al. also teaches where a base polymer containing recurring units (f) is used, the addition of a separate PAG may be omitted [0083] satisfying the closed “consisting of” language of instant claim 10. Hatakeyama et al. further teaches to the resist composition comprising the base polymer and the sulfonium salt having formula (A), an acid generator may be added so that the composition may function as a chemically amplified positive or negative resist composition. The acid generator is typically a compound (PAG) capable of generating an acid upon exposure to actinic ray or radiation. Although the PAG used herein may be any compound capable of generating an acid upon exposure to high-energy radiation, those compounds capable of generating sulfonic acid, imide acid (imidic acid) or methide acid are preferred. Suitable PAGs include sulfonium salts, iodonium salts, sulfonyldiazomethane, N-sulfonyloxyimide, and oxime-O-sulfonate acid generators [0092] and an example includes the following:
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[0100] which is equivalent to a photoacid generator of instant claim 1 having the formula (5A) where R101-R103 are each C6 hydrocarbyl groups and Xb- is an anion having the formula (6A’) where R111 is hydrogen and R112 is a C1 hydrocarbyl group. Hatakeyama et al. also teaches with the sulfonium salt having formula (A), the base polymer, and the acid generator, all defined above, other components such as an organic solvent, surfactant, dissolution inhibitor, and crosslinker may be blended in any desired combination to formulate a chemically amplified positive or negative resist composition [0117] (claims 1 and 10). Hatakeyama et al. further teaches the sulfonium salt of iodized benzoic acid has the following formula (A) [0053]:
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[0053] wherein X can be a (p+1)-valent C1-C20 linking group which may contain an ester and halogen moiety, p can be 1, m is 1 to 5, n can be 0, and R2 to R4 can each be a C6 aryl group in which at least one hydrogen (one or more or even all hydrogen atoms) may be substituted by a halogen [0054]. Hatakeyama et al. also teaches specific examples of the cation moiety include the following, but are not limited thereto [0057]:
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[0057] which are equivalent to the cations of formulae (Q-1) and (Q-2) respectively and structurally similar to the cation of formula (Q-24) of instant claims 1, 5-7, and 10; and a specific example of the anion moiety includes the following, but is not limited thereto [0058]:
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[page 22] which is structurally similar to the anion of formulae (Q-1), (Q-2), and (Q-24) of instant claims 1, 5-7, and 10 except the fluorine atoms and iso-propyl substituents are absent.
Hatakeyama et al. does not teach a specific example of X as the claimed linking group -C=O-O-CH(iso-propyl)-CF2-.
However, Domon et al. teaches a chemically-amplified positive resist composition for high energy beam exposure comprising: (A) a salt represented by the following general formula (1); and (B) a resin containing a repeating unit represented by general formula (U-1) that dissolves by acid action and increases solubility in an alkaline developer [0021]:
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[0038] wherein R01 and R02 a hydrogen atom, or a linear monovalent hydrocarbon group having 1 to 20 carbon atoms or a branched or a cyclic monovalent hydrocarbon group having 3 to 20 carbon atoms with which a hetero atom may be substituted or in which a hetero atom may be included, and R01 and R02 may mutually be bonded to form a cyclic structure together with a carbon atom bonded by the same and a carbon atom between the same [0044], L can be an ester bond formed together with the adjacent oxygen atom [0047], R0 can be a phenyl group which may be substituted with a halogen atom [0043], and each R101, R102 and R103 independently represents a linear monovalent hydrocarbon group having 1 to 20 carbon atoms or a branched or a cyclic monovalent hydrocarbon group having 3 to 20 carbon atoms with which a hetero atom may be substituted or in which a hetero atom may be included, and two or more of R101, R102 and R103 may mutually be bonded to form a cyclic structure together with a sulfur atom in the formula [0050] where a specific example includes the following formula (A-18):
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[page 5] which is structurally similar to the anion of formulae (Q-1), (Q-2), and (Q-24) of instant claims 1, 5-7, and 10 except a trifluoromethyl substituent is present instead of the claimed three iodine atoms. When the linking group X in formula (A) of Hatakeyama et al. is -C=O-O-CH(iso-propyl)-CF2- as taught by Domon et al., it is equivalent to the anion of formulae (Q-1), (Q-2), and (Q-24) of instant claims 1, 5-7, and 10. Domon et al. also teaches inventors of the present invention have carried out extended research and found that a sulfonium salt of a carboxylic acid with which a fluorine atom is substituted at α position is introduced into a resist composition to obtain a pattern with low LER. Based on that information, the present invention was accomplished. The present invention will be described in detail. In the following description, some chemical structures represented by chemical formulae contain an asymmetric carbon, thus including an enantiomer and a diastereomer. In this case, these isomers are collectively represented by one common formula. These isomers may be used alone or as a mixture [0039-0040] while Hatakeyama et al. teaches a resist film containing a sulfonium salt of iodized benzoic acid has the advantage that the sulfonium salt of iodized benzoic acid is highly effective for suppressing acid diffusion because of the large atomic weight of iodine. This leads to a reduced LWR. Since iodine is highly absorptive to EUV of wavelength 13.5 nm, it generates many secondary electrons during exposure, contributing to a higher sensitivity. Thus a resist material having a high sensitivity and low LWR may be designed. Using the resist material, a hole pattern of improved CDU can be formed [0032].
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 Hatakeyama et al. with the asymmetrical linking group of Domon et al. and arrive at the instant claims through routine experimentation of substituting known linking groups in order to reduce LER and LWR.
With regard to claims 15-18, Hatakeyama et al. teaches the resist composition is used in the fabrication of various integrated circuits. Pattern formation using the resist composition may be performed by well-known lithography processes. The process generally involves coating, prebaking, exposure, post-exposure baking (PEB), and development. If necessary, any additional steps may be added [0134] where the resist film is exposed to a desired pattern of high-energy radiation such as UV, deep-UV, EB, EUV, x-ray, soft x-ray, excimer laser light, γ-ray or synchrotron radiation, directly or through a mask [0136] and is developed with a developer in the form of an aqueous base solution for 3 seconds to 3 minutes, preferably 5 seconds to 2 minutes by conventional techniques such as dip, puddle and spray techniques. A typical developer is a 0.1 to 10 wt %, preferably 2 to 5 wt % aqueous solution of tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide (TEAH), tetrapropylammonium hydroxide (TPAH), or tetrabutylammonium hydroxide (TBAH) [0137] or in an alternative embodiment, a negative pattern may be formed via organic solvent development using a positive resist composition comprising a base polymer having an acid labile group. The developer used herein is preferably selected from among 2-octanone, 2-nonanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-hexanone, 3-hexanone, diisobutyl ketone, methylcyclohexanone, acetophenone, methylacetophenone, propyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, butenyl acetate, isopentyl acetate, propyl formate, butyl formate, isobutyl formate, pentyl formate, isopentyl formate, methyl valerate, methyl pentenoate, methyl crotonate, ethyl crotonate, methyl propionate, ethyl propionate, ethyl 3-ethoxypropionate, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, isobutyl lactate, pentyl lactate, isopentyl lactate, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate, methyl benzoate, ethyl benzoate, phenyl acetate, benzyl acetate, methyl phenylacetate, benzyl formate, phenylethyl formate, methyl 3-phenylpropionate, benzyl propionate, ethyl phenylacetate, and 2-phenylethyl acetate, and mixtures thereof [0138].
Response to Arguments
Applicant's arguments filed December 15, 2025 have been fully considered but they are not persuasive. In response to the 103 rejection over Hatakeyama in view of Domon, Hatakeyama broadly covers the claimed acid diffusion inhibitor. However, Applicant requests the Examiner to find unexpected results in the claimed invention. The claims presented should be allowed.
The Examiner does not find the results provided in the specification to be unexpected over the combined prior art Hatakeyama and Domon. The difference in LWR and CDU would have been expected based on the combined teachings of the prior art. Specifically, Hatakeyama’s objective is to achieve high sensitivity and minimal LWR [0019] and Domon’ objective is a salt which provides improved resolution for patterning and a pattern with reduced line edge roughness (LER) [0020]. Hatakeyama also teaches it is demonstrated in Tables 1 to 4 that resist compositions comprising a sulfonium salt having formula (A) within the scope of the invention offer a satisfactory resolution and improved LWR or CDU [0161] while Domon also teaches the resist compositions containing the salt represented by the general formula (1) as an acid diffusion control agent (Examples 49 to 86) all showed favorable resolution and favorable pattern rectangular property, and LER was a favorable value. Meanwhile, resist compositions in Comparative Examples 7 to 10 by using benzoate or a salt having no fluorine atom at .alpha. position of a carboxyl group as an acid diffusion control agent showed unfavorable resolution, LER and CDU, compared to Example [0149]. Therefore, the results provided in the instant specification would be expected based on the combined teachings of Hatakeyama and Domon.
Conclusion
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
/MARK F. HUFF/ Supervisory Patent Examiner, Art Unit 1737