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 Rejection of the previous action not repeated below are withdrawn based upon the arguments and amendments of the applicant.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 7-9 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]. Reactants including three epoxy groups include
PNG
media_image1.png
94
132
media_image1.png
Greyscale
and
PNG
media_image2.png
133
208
media_image2.png
Greyscale
[0010]
The hydroxybenzoic acid is reactive through both the carboxylic acid and hydroxyl groups
This is a new rejection.
Claims 1-4 and 7-11 are rejected under 35 U.S.C. 103 as being unpatentable over Neef et al. 7323289.
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
PNG
media_image3.png
208
325
media_image3.png
Greyscale
based upon the disclosed equivalence established as [0010] 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].
PNG
media_image4.png
177
247
media_image4.png
Greyscale
PNG
media_image5.png
163
372
media_image5.png
Greyscale
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).
PNG
media_image6.png
303
408
media_image6.png
Greyscale
PNG
media_image7.png
285
442
media_image7.png
Greyscale
PNG
media_image8.png
357
383
media_image8.png
Greyscale
PNG
media_image9.png
222
429
media_image9.png
Greyscale
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 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 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 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 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 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.
Claims 1-4 and 7-11 are rejected under 35 U.S.C. 103 as being unpatentable over Kishioka et al. CN 10383086.
Kishioka et al. CN 10383086 in synthesis example 1 reacts the tris(2, 3-glycidyl) isocyanurate ( and 3, 5-diiodo-2-hydroxyl benzoic acid to form the polymer illustrated in formula 6. [0095-0096].
PNG
media_image10.png
203
285
media_image10.png
Greyscale
The polymer is synthesis example 1 is combined with propylene glycol monomethyl lactate (solvent), light acid generating agent of triphenyl antimony acid sulfonium salt, tetramethoxyl methyl glycoluril (crosslinker) and p-toluenesulfonic acid pyridinium (thermal acid generator) to form a solution. This solution is filtered to form a formation for forming an anti-reflection film [0101]. The embodiments 1 to 11 modulated in combination for formation of anti-reflection film solution by spin coating, respectively coated on the silicon wafer. on the electric heating plate, the (baking minutes ' forming antireflection film thickness). FORMULA. FORMULA). market on the antireflection film by spin coating the photoresist solution (Sumitomo Chemical Industry (strain) produced, commodity name on the platen heater, heating for 1 minutes to form a photoresist layer 901. after the photoresist exposure light at 901 to 1.5 minutes of exposure light after heating ((61081 6X1) 08111-6 13 to 6). After developing the photoresist, measuring the antireflection film of film thickness, confirming there is no antireflection film mixed with photoresist layer [0112]. In addition, in the reaction with the compound of the above formula (1) represented by the use of benzoic acid compound is hydroxybenzoic acid compound having 2 carboxyl compounds such as phthalic acid compound under the condition, it is considered that the compound of carboxyl and hydroxyl, or 2 carboxyl groups of two of the above formula (1) of 2, 3-glycidyl epoxy ring opening reaction occurs. the hydroxyl benzoic acid compounds and phthalic acid compound is 1100 (8 - (0 = 0) 11-0 (in the formula, 8 represents an optionally substituted benzene, II is 0 or 1, when II = 0, acid compound, II = 1, representing the phthalic acid compound) represents the condition that 1 carboxyl groups with the above formula (1) of 2, 3-epoxypropyl reaction, transformation is the following formula (3). In addition, the remaining carboxyl group or hydroxyl group in the formula (3) to react with other 2, 3-glycidyl under the condition of formula (1) is considered to generate a reaction product of structure of formula (4). In addition, the structure of the generating formula (4) is the continuous state, namely oligomer (or polymer) of the reaction product. Therefore, it can be considered as benzoic acid compound, acid compound having 2 carboxyl groups of the compound, wherein the reaction product is that of a compound is compound of more than two, is an oligomer (or polymer), or is a mixture of two or more thereof. composition for forming an antireflection film of the invention contains the reaction product, can be any one of said conditions. the formula (1) as an intermediate for producing a composition for forming an antireflection film of the invention contains a reaction product represented by the compound can be listed out 2-propenyl-triglycidyl isocyanurate urine acid, phenyl diglycidyl isocyanurate urine acid and tris (2, 3-glycidyl) isocyanurate and the like. as for generating forming an antireflection film of the reaction product contained in the composition of the present invention using the benzoic acid compound, is not particularly limited, for example, it can use acid. In addition, it can use the benzoic acid compound by the following groups, said group is selected from methyl, ethyl and isopropyl alkyl such as methoxy, ethoxy and butoxy, alkoxy, methoxy and propoxy group such as alkoxy , gas atoms, atoms and atoms of halogen substituted, benzyl, phenyl, phenoxy, hydroxy, nitro, cyano, , methylthio and amino. as the benzoic acid compound, can be listed out such as benzoic acid, phthalic acid mono-ethyl ester, 2, 4-dibromo-benzoic acid, 4-methyl benzoic acid, 2 benzoic acid, 2, 3, 5 -acid, 2-Paniculta 4-nitrobenzoic acid, 4 acid, 4 acid, 4 acid, 4-tert-butylbenzoic acid, 3-methyl benzoic acid, 2-nitrobenzoic acid, 4-isopropoxy benzoic acid, 3-cyanobenzoic acid, 4-cyanobenzoic acid, 3 acid, and 3-trifluorodibromopropane, 4-methyl benzoic acid, 2 acid, 4, 6-benzoic acid, 4-methyl benzoic acid, 2-trifluorodibromopropane 4 acid, 4, 5-dichloro-benzene 1, 3-dicarboxylic acid, 5-amino 2, 4, 6 -triiodo-isophthalic acid, 1, 4-dicarboxylic acid, 2, 3, 5, 6-tetrabromo-benzene A 1, 4-dicarboxylic acid, 4, 5-dichloro phthalate, 5-methoxy-3-methyl phthalate, and 3, 4, 5, 6-tetrabromo phthalic acid and so on. In addition, as the benzoic acid compound can be listed out of acid compound, acid compound preferably having a halogen substituent. as the halogen substituent, from absorption of 2 excimer laser viewpoint, preferably (a), or iodine (0. can be exemplified as acid compound out of for example, 4 benzoic acid, 3 benzoic acid, 3 acid, 5-dihydroxybenzoic acid, 2-3 acid, 2.5-dichloro-3-hydroxyl-6-methoxy-benzoic acid, 2 acid, 4, 6-iodo-3-hydroxy benzoic acid, 2, 4, 6-one 3. A hydroxyl benzoic acid, 2-trifluorodibromopropane-4, 6-3 acid, 2 - -L-leucinamide 5 acid, 3-4 acid, 3, 5-bromine 4 a hydroxyl benzoic acid, 2, 4-dihydroxyl-5-bromine-benzoic acid, 3-trimethylpropargylsilane 5-nitro-4-hydroxyl benzoic acid, 2 acid, 4-chlorine-2-hydroxyl benzoic acid, 3, 5-diiodo-2-hydroxyl-benzoic acid, 3-methoxy-2-hydroxy-benzoic acid, 2-hydroxyl-6-isopropyl 3-methyl benzoic acid, and 4-3, 5-diiodo-2-hydroxy benzoic acid. in a reaction with a compound represented by the above formula (1), can only apply one of these acid compounds. In addition, it also can be used in combination of more than two of benzoic acid compound. For example, it can be combined using 4-nitryl benzoic acid and 3, 5-diiodo-2-hydroxybenzoic acid. Moreover, for example, can be combined using 4-hydroxyl benzoic acid and 4 cyanobenzoic acid. Moreover, for example, may use the combination of 4 benzoic acid and 2, 3, 5 iodine benzoic acid [0047-0054].
Kishioka et al. CN 10383086 does not exemplify embodiments with more than one epoxy reactive compound.
With respect to claims 1-4 and 7-11, it would have been obvious to modify synthesis example 1 by replacing a portion of the 3, 5-diiodo-2-hydroxyl benzoic acid with a benzoic acid compound having one epoxy reactive group such as benzoic acid, 2, 4-dibromo-benzoic acid, 4-methyl benzoic acid, cyanobenzoic acid disclosed at [0047-0054] and to use the resultant composition in the process of the examples with a reasonable expectation of the composition being useful as a resist underlayer based upon the disclosure that more than one benzoic acid compound can be used in the synthesis.
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.
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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark F 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.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 February 26, 2026