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 .
The response of the applicant has been read and given careful consideration. Rejection of the previous action not repeated below are withdrawn based upon the arguments and amendments of the applicant. Responses to the arguments appear after the fir5st rejection they are directed to.
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.
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.
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.
Claims 1-4 and 7-10 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Neef et al. 20040110089
Neef et al. 20040110089 in example 3, reacts Tris(2,3-epoxypropyl)isocyanurate (2.97 g), benzoic acid (1.83 g) and 4-hydroxybenzoic acid (2.07 g), in the presence of benzyltriethylammonium chloride (0.17 g), and propylene glycol n-propyl ether (61.83 g). This is then combined with powderlink 1174 (crosslinker) and p-toluene sulfonic acid and solvents PGMEA and ethyl lactate [0040-0043]. This was coated on a wafer, dried, a resist applied, exposed and post exposure baked and developed [0055-0056]. Anti-reflective coatings according to the invention have high etch rates. Thus, the cured anti-reflective coatings have an etch rate of at least about 10 .ANG./second, and preferably from about 11-15 .ANG./second when CF.sub.4 gas is used as the etchant. Additionally, at about 193 nm a cured layer formed from the inventive composition and having a thickness of about 320 .ANG. will have a k value (i.e., the imaginary component of the complex index of refraction) of at least about 0.40, and preferably at least about 0.50, and an n value (i.e., the real component of the complex index of refraction) of at least about 1.5, and preferably at least about 1.7. That is, the cured coatings will absorb at least about 95% of light at wavelengths of about 157, 193, 248, and 365 nm and at a layer thickness of about 320 .ANG.. The coatings can be used to obtain a resolution of less than about 150 .mu.m and preferably less than about 100 .mu.m in 193 nm photoresists [0024]
Reactants including three epoxy groups include
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[0010]
The hydroxybenzoic acid is reactive through both the carboxylic acid and hydroxyl groups
The molar ratio of C/(A+B is
(1.83g x 122.123 g/mol)/((2.97g/ 297.26 g/mol) + (2/07g/138.12 g/mol) which yields
0.015 moles/(0.01 moles + 0.015 moles) = 0.6
The applicant argues that Neef requires the 95% of the components to have a MW of less than 5000 g/mol. The examiner maintains the position that the composition of example 3 of Neef meets the limitations of the claims, noting that the instant specification admits that hydroxyl and carboxyl groups are functional groups which react with the epoxy, that the synthesis example 2 reacts triglycidylisocyanurate with adamantanedicarboxylic acid and adamantanecarboxylic acid (prepub at [0186].) The claims do not preclude R1 from including an ether, or carboxyl linkage/moiety, noting that a carboxyl linkage/moiety would surely be present in R1 in the polymer/oligomer produced by the reaction of inventive example 2 of the instant application.
Claims 1-4 and 7-11 are rejected under 35 U.S.C. 103 as being unpatentable over Neef et al. 7323289.
Neef et al. does not exemplify a composition which includes a diepoxide reactant.
It would have been obvious to one of ordinary skill in the art to modify example 3 by replacing at least part of the triepoxide containing reactant with
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based upon the disclosed equivalence established as [0010] and/or to etch the antireflective coating after patterning the resist based upon the disclosure at [0024] with a reasonable expectation of forming a useful antireflective underlayer and patterned resist.
Claims 1-4 and 7-11 are rejected under 35 U.S.C. 103 as being unpatentable over Endo et al. WO 2020004122
Endo et al. WO 2020004122 (machine translation attached) in example 3 reacts TAGICA (formula A-19) with dithiodiglycolic acid in the presence of ethyltriphenylphosphonium bromide (catalyst) and propylene glycol monomethyl ether (solvent). The resultant polymer (C-3) is combined with pyridinium trifluoromethanesulfonate (acid generator/crosslinkingcatalyst) Megafac R-40 (surfactant) and propylene glycol monomethyl ether to form a resist underlayer film forming composition [0061-0062]. The average MW of the epoxy adducts is 1000-100,000, but preferably 1300-20,000. The ratio of the epoxy to the reactant is 1:0.1 to 10 [0020].
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The underlayers of the examples are coated and baked to evaluate them [0065-0071]. The epoxy addition product of the present application is obtained by adding an epoxy compound represented by the above formula (1) to a carboxylic acid-containing compound, a carboxylic anhydride-containing compound, a hydroxy group-containing compound, a thiol group-containing compound, an amino group-containing compound, and an imide group. An epoxy adduct-forming compound such as a compound contained is formed by addition by a method known per se. Examples of the epoxy adduct-forming compound of the present application include, but are not limited to, the following formulas (B-1) to (B-53).
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Among these epoxy adduct-forming compounds, carboxylic acid-containing compounds (for example, the above formulas (B-1) to (B-25)) or thiol group-containing compounds (for example, the above formulas (B-7) and (B-10)) , (B-34) to (B-41)).The carboxylic acid-containing compound is preferably a dicarboxylic acid containing at least one sulfur atom (for example, the above formulas (B-7) and (B-11) to (B-17)).The dicarboxylic acid containing at least one sulfur atom is preferably an aliphatic dicarboxylic acid, particularly preferably dithioglycolic acid (formula (B-15) [0017-0019]. The epoxy adduct-forming compound is one or more compounds selected from the group consisting of carboxylic acid-containing compounds, carboxylic anhydride-containing compounds, hydroxy group-containing compounds, thiol group-containing compounds, amino group-containing compounds, and imide group-containing compounds (abstract). The addition of crosslinking agents is disclosed [0032-0039]. The coating of the underlayers, baking them, overcoating them with resists, drying the resist, exposing the resist and developing the resist is taught [0047-0051].
Endo et al. WO 2020004122 does not exemplify the composition with a polymer which is the product of the reaction between the triepoxide, a compound having two epoxy reactive groups and a compound having one reactive epoxy group and an aliphatic or aromatic ring.
With respect to claims 1-4,7 and 9, it would have been obvious to modify the processes of examples 3, by replacing a portion of the dithiodiglycolic acid with a benzoic acid B-18, a phenol B-30 or a mercapto benzene B-41 based upon the disclosed equivalence at [0017- 0019] based upon the use of one or more discussed in the abstract with a reasonable expectation of forming as useful underlayer composition.
With respect to claims 1-4 and 7-9, it would have been obvious to modify the processes of examples 3, by replacing a portion of the dithiodiglycolic acid with a benzoic acid B-18, a phenol B-30 or a mercapto benzene B-41 so that the molar ratio of monoreactive compound/(epoxy + direactive compound) is 0.5 to 2 based upon the disclosed equivalence at [0017- 0019] and adding a crosslinking agents, such as those disclosed at [0032-0039] based upon the disclosure to do so with a reasonable expectation of forming a useful resist underlayer.
With respect to claims 1-4 and 7-11, it would have been obvious to modify the processes of examples 3, by replacing a portion of the dithiodiglycolic acid with a benzoic acid B-18, a phenol B-30 or a mercapto benzene B-41 so that the molar ratio of monoreactive compound/(epoxy + direactive compound) is 0.5 to 2 based upon the disclosed equivalence at [0017- 0019], adding a crosslinking agents, such as those disclosed at [0032-0039] and extending the processes where the composition of example 3 are coated and baked by overcoating resist composition , drying the resist to remove the solvent, exposing the resist and developing the resist pattern using developers as disclosed at [0047-0051] with a reasonable expectation of forming useful resist patterns.
With respect to claims 1-4,7 and 9, it would have been obvious to modify the processes of examples 3, by replacing a portion of the dithiodiglycolic acid with a benzoic acid B-18, a phenol B-30 or a mercapto benzene B-41 and a compound having two reactive sites such as such as B-19, B-20, B-23., B-24, B-31 to B-33, B-28, B-29 so that the molar ratio of monoreactive compound/(epoxy + direactive compound) is 0.5 to 2 based upon the disclosed equivalence at [0017- 0019] based upon the use of one or more discussed in the abstract with a reasonable expectation of forming as useful underlayer composition.
With respect to claims 1-4 and 7-9, it would have been obvious to modify the processes of examples 3, by replacing a portion of the dithiodiglycolic acid with a benzoic acid B-18, a phenol B-30 or a mercapto benzene B-41 and a compound having two reactive sites such as such as B-19, B-20, B-23., B-24, B-31 to B-33, B-28, B-29 so that the molar ratio of monoreactive compound/(epoxy + direactive compound) is 0.5 to 2 based upon the disclosed equivalence at [0017- 0019] based upon the use of one or more discussed in the abstract and adding a crosslinking agents, such as those disclosed at [0032-0039] based upon the disclosure to do so with a reasonable expectation of forming a useful resist underlayer.
With respect to claims 1-4 and 7-11, it would have been obvious to modify the processes of examples 3, by replacing a portion of the dithiodiglycolic acid with a benzoic acid B-18, a phenol B-30 or a mercapto benzene B-41 and a compound having two reactive sites such as such as B-19, B-20, B-23., B-24, B-31 to B-33, B-28, B-29 so that the molar ratio of monoreactive compound/(epoxy + direactive compound) is 0.5 to 2 based upon the disclosed equivalence at [0017- 0019] based upon the use of one or more discussed in the abstract and adding a crosslinking agents, such as those disclosed at [0032-0039], extending the processes where the composition of example 3 are coated and baked by overcoating resist composition , drying the resist to remove the solvent, exposing the resist and developing the resist pattern using developers as disclosed at [0047-0051] with a reasonable expectation of forming useful resist patterns.
In the response of 2/3/2026, the applicant argues that Endo et al. WO 2020004122 does not teach compounds having one epoxy reactive group and an aliphatic or aromatic ring.. The examiner points to a benzoic acid B-18, a phenol B-30 or a mercapto benzene B-41, which are taught as reactants. The claim language is open to other reactant due to the open “comprising” language of the claims.
In the response of 5/27/2026, the applicant has a basis for limiting the relative amounts of the monoreactive component, but there is no evidence that the narrowing the range yields a material benefit or unobvious result to the composition or process using it, particularly for the breadth of underlayer composition bounded by the claim language.
Claims 1-4 and 7-11 are rejected under 35 U.S.C. 103 as being unpatentable over Kishioka et al. 20090117493.
Kishioka et al. 20090117493 teaches in synthesis example 1, the reaction of 175 g of tris (2,3-epoxypropyl) isocyanuric acid (trade name TEPIC, manufactured by Nissan Chemical Industries, Ltd.), 628 g of 3,5-diiodo-2-hydroxybenzoic acid, and 9.2 g of benzyltriethylammonium chloride are propylene glycol After dissolving in 3250 g of monomethyl ether, the mixture was reacted at 130 ° C. for 24 hours to obtain a solution containing the reaction product. In addition, it is thought that the reaction product contains an isocyanuric acid compound in which a 2,3-epoxypropyl group is converted to a group of formula (5) and an oligomer (or polymer) having a structure of formula (6).
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[0074-0075]. Synthesis example 2 is the reaction of After dissolving 457 g of tris (2,3-epoxypropyl) isocyanuric acid (trade name TEPIC, manufactured by Nissan Chemical Industries, Ltd.), 407 g of 4-hydroxybenzoic acid and 136 g of 4-cyanobenzoic acid in 1000 g of propylene glycol monomethyl ether , And reacted at 130 ° C. for 24 hours to obtain a solution containing the reaction product. In addition, it is thought that the reaction product contains an isocyanuric acid compound in which a 2,3-epoxypropyl group is converted to a group of formula (7) or formula (8) [0076-0077]. 19.8 g of the reaction solution obtained in Synthesis Example 2 was added to 95 g of propylene glycol monomethyl ether, 1.00 g of tetramethoxymethyl glycoluril (trade name Powder Link 1174 manufactured by Mitsui Cytec Co., Ltd.), 0.05 g of pyridinium-p-toluenesulfonate. And 0.002 g of a surfactant Megafac R-30 (Dainippon Ink Chemical Co., Ltd.) was added to make a solution. Thereafter, the solution was filtered using a polyethylene microfilter having a pore size of 0.10 μm, and then filtered using a polyethylene microfilter having a pore size of 0.05 μm to prepare an antireflection film-forming composition solution [0082]. Test of intermixing with photoresist Each of the antireflection film-forming composition solutions prepared in Examples 1 to 11 was applied onto a silicon wafer by a spinner. It was baked on a hot plate at 205 ° C. for 1 minute to form an antireflection film (film thickness: 0.08 μm). On these antireflection films, a commercially available photoresist solution (manufactured by Sumitomo Chemical Co., Ltd., trade name: PAR710) was applied with a spinner, and heated on a hot plate at 90 ° C. for 1 minute to form a photoresist layer. Formed. After exposure of the photoresist, post exposure bake was performed at 90 ° C. for 1.5 minutes. After developing the photoresist, the film thickness of the antireflection film was measured, and it was confirmed that no intermixing occurred between the antireflection film and the photoresist layer [0084]. Evaluation of Photoresist Pattern Shape Each of the antireflection film forming composition solutions prepared in Examples 1 to 11 was applied onto a silicon wafer by a spinner. It was baked on a hot plate at 205 ° C. for 1 minute to form an antireflection film (film thickness: 0.08 μm). A commercially available photoresist solution (trade name: TARF-P6111 manufactured by Tokyo Ohka Kogyo Co., Ltd.) was applied to the upper layer of these antireflection films with a spinner and heated at 90 ° C. for 1 minute on a hot plate. A layer (thickness 0.33 μm) was formed. Then, using a PAS5500 / 990 scanner (wavelength 193 nm, NA, σ: 0.63, 0.87 / 0.57 (Annuler)) manufactured by ASML, the line width of the photoresist and the width between the lines are 0 after development. It was 0.09 μm, ie 0.09 μmL / S (dense line), and exposure was performed through a mask set to form nine such lines. Then, after exposure for 1 minute at 130 ° C. on a hot plate, heating, cooling, and development using 0.26N tetramethylammonium hydroxide developer in an industrial standard 60 second single paddle process, A resist pattern was formed [0086]. Only one kind of these benzoic acid compounds can be used for the reaction with the compound represented by the formula (1). Two or more benzoic acid compounds can be used in appropriate combination. For example, 4-nitrobenzoic acid and 3,5-diiodo-2-hydroxybenzoic acid can be used in combination. Further, for example, 4-hydroxybenzoic acid and 4-cyanobenzoic acid can be used in combination. Further, for example, 4-hydroxybenzoic acid and 2,3,5-triiodobenzoic acid can be used in combination [0035]. The present invention relates to an antireflection film-forming composition for lithography for an antireflection film having strong absorption in light having a short wavelength, particularly light having a wavelength of 193 nm or 157 nm. The present invention also provides an antireflection film-forming composition that can be used in a lithography process for manufacturing a semiconductor device using irradiation light of an ArF excimer laser (wavelength 193 nm) or F2 excimer laser (wavelength 157 nm). That is. In addition, the present invention effectively absorbs reflected light from the substrate when ArF excimer laser or F2 excimer laser irradiation light is used for microfabrication, and does not cause intermixing with the photoresist layer. An antireflection film having a high dry etching rate and an antireflection film forming composition therefor are provided. Moreover, this invention is providing the antireflection film which can form the photoresist pattern which does not have a large skirting shape in the lower part, and the antireflection film formation composition for it. Another object of the present invention is to provide a method for forming an antireflection film for lithography using such an antireflection film-forming composition and a method for forming a photoresist pattern [0010].
Kishioka et al. 20090117493 does not exemplify embodiments with ratio of compounds having one epoxy reactive moiety within the recited range or the use of the composition of the examples in etching processes.
With respect to claims 1-4 and 7-10, it would have been obvious to modify synthesis example 2 by increasing the amount of the cyanobenzoic acid and decreasing the amount of the hydroxybenzoic acid so that the ratio of C/(A+B) is 0.5 to 2 based upon the broad disclosure that mixtures of two or more benzoic acid compounds can be used at [0035] and to use the resultant polymer as in example 11 with a reasonable expectation of the composition being useful as a resist underlayer and useful resist pattern based upon the disclosure that more than one benzoic acid compound can be used in the synthesis.
With respect to claims 1-4 and 7-11, it would have been obvious to modify synthesis example 2 by increasing the amount of the cyanobenzoic acid and decreasing the amount of the hydroxybenzoic acid so that the ratio of C/(A+B) is 0.5 to 2 based upon the broad disclosure that mixtures of two or more benzoic acid compounds can be used at [0035] and to use the resultant polymer as in example 11, followed by etching of the underlayer and substrate as taught at [0010] with a reasonable expectation of the composition being useful as a resist underlayer in the patterning and etching processes based upon the disclosure that more than one benzoic acid compound can be used.
In the response of 5/27/2026, the applicant has a basis for limiting the relative amounts of the monoreactive component, but there is no evidence that the narrowing the range yields a material benefit or unobvious result to the composition or process using it, particularly for the breadth of underlayer composition bounded by the claim language.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Sakaida et al. 20170045820 reacts 7.00 g of monoallyl diglycidyl isocyanurate (available from Shikoku Chemicals Corporation), 3.93 g of 5,5-diethyl barbituric acid (available from HACHIDAI PHARMACEUTICAL CO., LTD.), 1.51 g of 4-(methylsulfonyl)benzoic acid (available from Tokyo Chemical Industry Co., Ltd.), and 0.47 g of ethyltriphenylphosphonium bromide (available from Sigma-Aldrich) were added to 73.14 g of propylene glycol monomethyl ether and dissolved. The reactor was purged with nitrogen, and a reaction was caused at 135° C. for 4 hours to obtain a polymer solution. The polymer solution was not clouded even under cooling to room temperature. The polymer solution has good solubility in propylene glycol monomethyl ether. The polymer in the obtained solution was analyzed by GPC. The weight average molecular weight in terms of standard polystyrene was 2,600. The degree of distribution was 3.448. The polymer obtained in this Synthesis Example has structural units of the following Formulae (4a-1) and (5a-1) and a structure of the following Formula (1-1) at a terminal [0063]. The other examples as re similar. The monoreactive compound can be used in 1-30 wt% [0037] (which yields a range of ~ 0.01 to 0.42)
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 Martin J Angebranndt whose telephone number is (571)272-1378. The examiner can normally be reached 7-3:30 pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Ching-Yu (Coris) Fung can be reached at 571-270-5713. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 June 10, 2026
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