DETAILED ACTION
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
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Election/Restrictions
Applicant's election with traverse of Group I, claims 1-3, 8, 9, and 15-19, in the reply filed on June 4, 2026 is acknowledged. The traversal is on the ground(s) that the subject matter of all claims and species is sufficiently related that a thorough search for the subject matter of any one Group would encompass a search for the subject matter of the remaining claims and species. Thus, the search could be made without serious burden. This is not found persuasive because the claims are directed to different compounds/polymers which would require a different field of search. Specifically, a polymer as claimed would require a search in a separate class than a compound. Additionally, a polymer would require a different search regarding the starting compounds than compared to a compound search. Further, the different inventions do not make a contribution over the prior art. Thus, a serious burden is required.
The requirement is still deemed proper and is therefore made FINAL.
Claims 4-7 and 10-14 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected Groups, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on June 4, 2026.
Specification
Applicant is reminded of the proper content of an abstract of the disclosure.
In chemical patent abstracts for compounds or compositions, the general nature of the compound or composition should be given as well as its use, e.g., “The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics.” Exemplification of a species could be illustrative of members of the class. For processes, the type of reaction, reagents and process conditions should be stated, generally illustrated by a single example unless variations are necessary.
The abstract of the disclosure is objected to because it fails to include formula (100). A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
The disclosure is objected to because of the following informalities: it is unclear how Comparative Examples A2, A3, A4, B2, and C2 are in fact comparative as they read on the polymer as defined in claim 1.
Appropriate correction is required.
Claim Objections
Claims 1 and 3 are objected to because of the following informalities: Claim 1 recites “
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” which should be omitted. Claim 1 also recites “(in…compound)” in which the parentheses should be omitted. Claim 3 recites “
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” which should be omitted. Claim 3 also recites “(in…respectively)” in which the parentheses should be omitted. Appropriate correction is required. The Examiner would like to note that while claims 4, 5, 7, 10, 12, 13, and 14 are currently withdrawn, these claims also have similar objectionable subject as claims 1 and 3.
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 8 and 9 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 8 recites “according to claim 3, wherein the epoxy group-containing compound, the compound containing two or more epoxy groups, or Q1 has a heterocyclic structure”. However, the “compound containing two or more epoxy groups” is recited in withdrawn claim 5 and “Q1” is recited in withdrawn claim 7. Claim 9 recites “according to claim 2, wherein at least one of L1 to L3 is an alkenylene group having 2 to 10 carbon atoms”. However, claim 2 recites L0 while claim 3 recited L1 and claim 7 recites L2 and L3. 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.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 2, and 15-19 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-25 of U.S. Patent No. 11,454,889. Although the claims at issue are not identical, they are not patentably distinct from each other because both the instant claims and patented claims are directed to compositions comprising a compound, a solvent, a crosslinkable compound, and an acid catalyst (acid generator), and methods of producing patterns/semiconductors thereof. Specifically, ‘889 recites the following compounds:
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which encompass a compound having a structure represented by Formula (100) of instant claims 1 and 2 when L0 is an ester bond or an ether bond respectively, T0 is a single bond, Ar is a substituted aromatic ring group having 6 carbon atoms, and n is 1 where R0 is a monovalent organic group. Claims 6-25 encompass instant claims 17-19.
Claims 1, 2, 18, and 19 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-5 and 8 of U.S. Patent No. 11,112,696. Although the claims at issue are not identical, they are not patentably distinct from each other because both the instant claims and patented claims are directed to compositions comprising a compound and a solvent, and methods of producing patterns/semiconductors thereof. Compound (2a-1) of ‘696 encompasses a compound having a structure represented by Formula (100) of instant claims 1 and 2 when L0 is an ester bond, T0 is a single bond, Ar is a substituted aromatic ring group having 6 carbon atoms, and n is 2 where R0 is a hydroxy group. The method of claim 5 of ‘696 encompasses the methods of instant claims 18 and 19.
Claims 1-3, 8, and 9 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 10,570,248. Although the claims at issue are not identical, they are not patentably distinct from each other because both the instant claims and patented claims are directed to compositions comprising a compound, a solvent, a crosslinking agent, and a crosslinking catalyst (acid generator). Specifically, component (A) of ‘248 which is a compound obtained by reacting a cinnamic acid compound of formula (1) with a compound having at least one epoxy group in the molecule where formula (1) is defined as: R1-R5 are each independently a substituent selected from a hydrogen atom, a halogen atom, a C1-6 alkyl, a C1-6 haloalkyl, a C1-6 alkoxy, a C1-6 haloalkoxy, a C3-8 cycloalkyl, a C3-8 halocycloalkyl, a C2-6 alkenyl, a C2-6 haloalkenyl, a C3-8 cycloalkenyl, a C3-8 halocycloalkenyl, a C2-6 alkynyl, a C2-6 haloalkynyl, a (C1-6 alkyl) carbonyl, a (C1-6 haloalkyl) carbonyl, a (C1-6 alkoxy) carbonyl, a (C1-6 haloalkoxy) carbonyl, a (C1-6 alkylamino) carbonyl, a (C1-6 haloalkyl) aminocarbonyl, a di(C1-6 alkyl) aminocarbonyl, cyano, and nitro encompasses the instantly claimed compound having a structure represented by Formula (100) of instant claims 1, 2, 8, and 9, specifically a compound which is the reaction product of an epoxy group-containing compound (e.g. heterocyclic compound), and a compound represented by Formula (101) when R1 is a group having reactivity with an epoxy group (carboxy group), L1 is an alkenylene group having 2 carbon atoms, Ar is an optionally substituted aromatic ring having 6 to 40 carbon atoms, and n is 1 to 3.
Claims 1-3 and 15-19 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 12,242,194. Although the claims at issue are not identical, they are not patentably distinct from each other because both the instant claims and patented claims are directed to a composition comprising an epoxy adduct, an acid generator, and a crosslinking agent, and methods of producing patterns/semiconductors thereof. The epoxy adduct (C) of ‘194 obtained by reacting an epoxy group-containing compound (A) represented by formula (1) and an epoxy adduct-forming compound (B), specifically a carboxylic acid of formula (2) where formula (1) is defined as: PA is an aliphatic or aromatic hydrocarbon, Ep is formula 1A, n1 is 1, n2 is 0 or 1, n3 is 1, and n4 is 4, and formula (2) is defined as: n8 is 1, m6 is 1, Ar1 is a C6-40 arylene group having a substituent (e.g. nitro), n5 is 1, and n7 is 1 when R1 is an optionally branched alkyl group having a carbon atom number of 3 to 19 encompasses the instantly claimed compound having a structure represented by Formula (100) of instant claims 1, 2, 8, and 9, specifically a compound which is the reaction product of an epoxy group-containing compound (e.g. heterocyclic compound), and a compound represented by Formula (101) when R1 is a group having reactivity with an epoxy group (carboxy group), L1 is a single bond, Ar is a substituted aromatic ring having 6 to 40 carbon atoms, and n is 1 to 3. The methods of claims 4 and 5 of ‘194 encompass the methods of instant claims 18 and 19.
Claims 1-3, 9, and 17-19 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 of U.S. Patent No. 11,155,684. Although the claims at issue are not identical, they are not patentably distinct from each other because both the instant claims and patented claims are directed to compositions comprising a compound and a solvent, and methods of. Specifically, compound (C) of ‘684 having formula (1) which is a compound which is a reaction product of an epoxy group-containing compound (A) and a cinnamic acid (B) having the partial structural of formula (1) where formula (1) is defined as: R1 and R2 are each independently a hydrogen atom, a C1-10 alkyl group, or a C6-40 aryl group, five R3s are each independently a hydrogen atom, a hydroxy group, a C1-10 alkoxy group, a C1-10 alkyl group, a nitro group, or a halogen atom encompasses the instantly claimed compound having a structure represented by Formula (100) of instant claims 1, 2, and 9, specifically a compound which is the reaction product of an epoxy group-containing compound, and a compound represented by Formula (101) when R1 is a group having reactivity with an epoxy group (carboxy group), L1 is an alkenylene group having 2 carbon atoms, Ar is an optionally substituted aromatic ring having 6 carbon atoms, and n is 1 to 3. The methods of claims 5-24 encompass the methods of instant claims 17-19.
Claim Rejections - 35 USC § 102
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.
Claims 1, 2, and 15-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Endo et al. (WO2019031556). U.S. 11,454,889 is being used as the English translation.
Endo et al. teaches in Production Example 1, To 4.87 g of the resin solution (solid content: 23.75% by mass) obtained in Synthesis Example 1, 0.23 g of tetramethoxymethyl glycoluril (trade name: POWDERLINK [registered trademark] 1174 available from Nihon Cytec Industries Inc.) as a thermal crosslinker, 0.01 g of pyridinium p-toluenesulfonate as a catalyst for a thermal crosslinking reaction (acid generator), 0.001 g of surfactant (trade name: MEGAFACE [trade name] R-40 available from DIC Corporation, fluorosurfactant), 9.31 g of propylene glycol monomethyl ether, and 5.58 g of propylene glycol monomethyl ether acetate were added to prepare a solution of stepped substrate-coating composition [col 51 lines 15-28] (claims 1, 15, and 16) wherein Synthesis Example 1 was prepared as followed: 5.22 g of propylene glycol monomethyl ether was added to 9.00 g of epoxy group-containing benzene fused ring compound (trade name: EPICLON HP-4700, epoxy value: 162 g/eq., available from DIC Corporation, Formula (B-12)), 9.84 g of N-(4-hydroxyphenyl)methacrylamide, 1.04 g of ethyltriphenylphosphonium bromide, and 0.02 g of hydroquinone, and the mixture was heated and stirred under a nitrogen atmosphere at 100° C. for 25 hours. By adding 20 g of cation exchange resin (trade name: DOWEX [registered trademark] 550A, Muromachi Technos Co., Ltd.) and 20 g of anion exchange resin (trade name: AMBERLITE [registered trademark] 15JWET, ORGANO CORPORATION) to the obtained solution, an ion exchange treatment was performed at room temperature for 4 hours. The cation and anion exchange resins were separated to obtain a solution of compound (E). The obtained compound (E) corresponded to Formula (E-11), and the weight average molecular weight Mw measured by GPC in terms of polystyrene was 1,900. The compound (E) had no residual epoxy group, and the molar ratio (partial structure (II))/(partial structure (I)+partial structure (II)) was 0.5 [col 49 lines 31-54] wherein compound (E-11) is the following:
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[col 31-32] which is equivalent to a compound having a structure represented by Formula (100) of instant claims 1 and 2 when L0 is an ether bond, T0 is a single bond, Ar is a substituted aromatic ring group having 6 carbon atoms, and n is 1 where R0 is a monovalent organic group.
With regard to claim 17, Endo et al. teaches in Examples 1 to 8, the stepped substrate-coating compositions prepared in Production Examples 1 to 8, respectively, were each applied to a silicon wafer using a spin coater (spin coating). In Comparative Examples 1 to 4, the stepped substrate-coating compositions prepared in Comparative Production Examples 1 to 4, respectively, were each applied to a silicon wafer using a spin coater (spin coating). Subsequently, each of the compositions was heated on a hot plate at 170° C. for 1 minute to form a coating film having a thickness of 200 nm [col 53 lines 54-63].
With regard to claim 18, Endo et al. teaches the stepped substrate-coating film (flattened film) obtained by the present invention is coated with a resist film, the resist film is subjected to exposure and development by lithography, to form a resist pattern, and the substrate can be processed in accordance with the resist pattern. In this case, the stepped substrate-coating film (flattened film) is a resist underlayer film, and the stepped substrate-coating composition is a resist underlayer film-forming composition [col 46 lines 9-16] and a resist is applied to the resist underlayer film, irradiated with light or an electron beam using a predetermined mask, and subjected to development, rinsing, and drying [col 46 lines 17-19].
With regard to claim 19, Endo et al. teaches a semiconductor device can be manufactured by steps of forming the resist underlayer film from the resist underlayer film-forming composition on a semiconductor substrate, forming a resist film on the resist underlayer film, forming a resist pattern by irradiation of the resist film with light or an electron beam and development, etching the resist underlayer film using the formed resist pattern, to form a patterned resist underlayer film, and processing the semiconductor substrate by using the patterned resist underlayer film [col 48 lines 7-16].
Claim 1 recites “A resist underlayer film-forming composition” which refers to the intended use of the composition. It has been held that a recitation with respect to the manner in which a claimed composition is intended to be used does not differentiate the claimed composition from a prior art composition satisfying the claimed structural limitations. Ex Parte Masham, 2, USPQ2d 1647 (1987). This recitation of the composition is drawn to intended use; therefore, this limitation does not add any patentable weight to the claim (MPEP 2106). Thus, the composition of Endo et al. is the same as instantly claimed.
Claims 1, 2, and 16-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hashimoto et al. (WO2018052130). U.S. 11,112,696 is being used as the English translation.
Hashimoto et al. teaches in Example 5, To 1.23 g of the reaction product-containing solution as obtained in Synthesis Example 6 were added 0.27 g of 1,3,4,6-tetraglycidyl glycoluril (crosslinking agent) and 18.50 g of propylene glycol monomethyl ether. The resulting solution was filtered through a microfilter made of polyethylene and having a pore diameter of 0.02 μm, and thus a protective film-forming composition was prepared [col 28 lines 20-27] (claims 1 and 16) wherein Synthesis Example 6 was prepared as followed: 10.72 g of triglycidyl isocyanurate, 19.01 g of 3,5-dihydroxybenzoic acid, and 0.26 g of ethyltriphenylphosphonium bromide were dissolved in 69.97 g of propylene glycol monomethyl ether, and then the reaction was allowed to proceed at 140° C. for 24 hours, giving a solution containing a reaction product (solids content: 30% by mass). GPC analysis of the obtained reaction product revealed that the weight-average molecular weight of the reaction product, calculated as a standard polystyrene equivalent, was 770 [col 26 lines 40-50] which is equivalent to a compound having a structure represented by Formula (100) of instant claims 1 and 2 when L0 is an ester bond, T0 is a single bond, Ar is a substituted aromatic ring group having 6 carbon atoms, and n is 2 where R0 is a hydroxy group.
With regard to claims 17-19, Hashimoto et al. teaches the protective film-forming composition of the present invention is applied onto such a semiconductor substrate by appropriate application means such as a spinner or coater. The applied composition is then baked with heating means such as a hot plate to form a protective film [col 23 lines 53-57]; next, a resist pattern is formed on the protective film. The formation of the resist pattern can be accomplished through common processes, i.e., application of a photoresist solution to the protective film, followed by prebake, exposure, post-exposure bake abbreviated as PEB (if necessary), development, and rinsing [col 24 lines 6-11]; next, the protective film is dry-etched with the formed resist pattern serving as a mask [col 24 lines 57-58].
Claim 1 recites “A resist underlayer film-forming composition” which refers to the intended use of the composition. It has been held that a recitation with respect to the manner in which a claimed composition is intended to be used does not differentiate the claimed composition from a prior art composition satisfying the claimed structural limitations. Ex Parte Masham, 2, USPQ2d 1647 (1987). This recitation of the composition is drawn to intended use; therefore, this limitation does not add any patentable weight to the claim (MPEP 2106). Thus, the composition of Hashimoto et al. is the same as instantly claimed.
Claims 1, 2, 9, and 15-17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ito et al. (U.S. 10,570,248).
Ito et al. teaches in Example 13, a composition comprising compound PA6, component PB1, compound PTSA, and solvent PM [col 41 lines 1-20] (claim 1) wherein PTSA is p-toluenesulfonic acid monohydrate [col 38] which is equivalent to an acid generator of instant claim 15; PB1 is a crosslinking agent (claim 16); and PA6 is obtained in the following Synthesis Example 6: In 73.2 g of PM, 11.1 g of TEPIC-L, 20.0 g, of MCA, and 0.26 g of BTEAC were dissolved, and the resulting solution was allowed to react at 120° C. for 20 hours to obtain a photo-orientation compound (solid-content concentration: 30% by mass) (PA6). The epoxy value of the obtained compound was measured, and it was confirmed that epoxy groups with which all the MCA had reacted disappeared [col 39 lines 15-24] wherein PM is propylene glycol monomethyl ether, TEPIC-L is trifunctional epoxy compound, manufactured by Nissan Chemical Industries, Ltd., specifically tris(2,3-epoxypropyl)isocyanurate, MCA is p-methoxycinnamic acid, and BTEAC is benzyl triethyl ammonium chloride which is equivalent to compound having a structure represented by Formula (100) of instant claims 1, 2, and 9 when L0 is an alkenylene group having 2 carbon atoms, T0 is a single bond, Ar is a substituted aromatic ring having 6 carbon atoms, n is 1 where R0 is as monovalent organic group.
With regard to claim 17, Ito et al. teaches on an alkali-free glass, each of the cured-film formation compositions of Examples 8 to 15, and 17 to 18 and Comparative Example 1 was applied using a spin coater in a film thickness of 200 nm. Subsequently, each of the resulting coatings was heated and dried at a temperature of 100° C. for 60 seconds on a hot plate to form a cured film on the corresponding one of the substrates [col 41 lines 53-59].
Claim 1 recites “A resist underlayer film-forming composition” which refers to the intended use of the composition. It has been held that a recitation with respect to the manner in which a claimed composition is intended to be used does not differentiate the claimed composition from a prior art composition satisfying the claimed structural limitations. Ex Parte Masham, 2, USPQ2d 1647 (1987). This recitation of the composition is drawn to intended use; therefore, this limitation does not add any patentable weight to the claim (MPEP 2106). Thus, the composition of Ito et al. is the same as instantly claimed.
Claims 1, 2, and 15-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Endo et al. (U.S. 2018/0181001). Corresponds to U.S. 12,242,194 above.
Endo et al. teaches in Example 4, 3 43.72 g of propylene glycol monomethyl ether was added to 9.00 g of trade name EPICLON HP-4700 (available from DIC Corporation, formula (1-7)), 5.30 g of 4-butoxybenzoic acid, 3.93 g of n-octanoic acid, and 0.51 g of ethyltriphenylphosphonium bromide, and the mixture was heated and refluxed with stirring under a nitrogen atmosphere for 18 hours. To the obtained reaction solution, 19 g of cation exchange resin (trade name: DOWEX (registered trademark) 550A, Muromachi Technos Co., Ltd.) and 19 g of anion exchange resin (trade name: amberlite (registered trademark) 15JWET, ORGANO CORPORATION) were added, and the mixture was subjected to an ion exchange treatment at room temperature for 4 hours. The ion exchange resins were separated. The obtained compound solution contained a polymer of formula (3-4). The weight average molecular weight Mw thereof measured in terms of polystyrene by GPC was 1,800. To 3.43 g of this compound solution (solid content: 29.15% by mass), 0.20 g of tetramethoxymethyl glycoluril (trade name: POWDERLINK (registered trademark) 1174 available from Nihon Cytec Industries Inc.) (crosslinking agent), 0.01 g of pyridinium p-toluenesulfonate (acid generator), 0.001 g of surfactant (product name: MEGAFACE (trade name) R-40 available from DIC Corporation, fluorosurfactant), 13.68 g of propylene glycol monomethyl ether, and 6.90 g of propylene glycol monomethyl ether acetate were added to prepare a solution of resist underlayer film-forming composition [0116-0117] (claims 1, 15, and 16) wherein formula (3-4) is the following:
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[0075] which is equivalent to a compound having a structure represented by Formula (100) of instant claims 1 and 2 when L0 is an ether bond, T0 is a single bond, Ar is a substituted aromatic ring group having 6 carbon atoms, and n is 1 where R0 is a monovalent organic group.
With regard to claim 17, Endo et al. teaches the resist underlayer film-forming composition prepared in each of Examples 4, 8, 9, 12 to 15, 17, and 21 was applied to a silicon wafer, and heated on a hot plate at 215° C. for 1 minute, to form a film of the resist underlayer film-forming composition [0161].
With regard to claims 18 and 19, Endo et al. teaches a resist film is applied to an upper layer of the resist underlayer film obtained from the resist underlayer film-forming composition of the present invention, exposed, and developed to form a resist pattern, and a substrate is processed by dry etching through the resist pattern using etching gas or the like [0164].
Claim 1 recites “A resist underlayer film-forming composition” which refers to the intended use of the composition. It has been held that a recitation with respect to the manner in which a claimed composition is intended to be used does not differentiate the claimed composition from a prior art composition satisfying the claimed structural limitations. Ex Parte Masham, 2, USPQ2d 1647 (1987). This recitation of the composition is drawn to intended use; therefore, this limitation does not add any patentable weight to the claim (MPEP 2106). Thus, the composition of Endo et al. is the same as instantly claimed.
Claims 1, 2, 9, and 15-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Sakamoto et al. (U.S. 2018/0086886). Corresponds to U.S. 11,155,684 above.
Sakamoto et al. teaches in Production Example 1, to 2.61 g of the resin solution (solid content: 26.80% by mass) obtained in Synthesis Example 1, 0.001 g of surfactant (product name: MEGAFACE (trade name) R-40 available from DIC Corporation, fluorosurfactant), 4.60 g of propylene glycol monomethyl ether, and 2.79 g of propylene glycol monomethyl ether acetate were added to prepare a solution of composition for coating a stepped substrate [0104] (claim 1) in which Synthesis Example 1 is prepared as followed: 37.44 g of propylene glycol monomethyl ether was added to 7.50 g of epoxy group-containing benzene fused ring compound EPICLON HP-4700 (trade name, epoxy value: 165 g/eq., available from DIC Corporation, Formula (A-2)), 8.10 g of 4-methoxycinnamic acid, 0.42 g of ethyltriphenylphosphonium bromide, and 0.03 g of hydroquinone, and the mixture was heated and refluxed under a nitrogen atmosphere for 17 hours. To the obtained polymer solution, 16 g of cation exchange resin (trade name: DOWEX (registered trademark) 550A, Muromachi Technos Co., Ltd.) and 16 g of anion exchange resin (trade name: amberlite (registered trademark) 15JWET, ORGANO CORPORATION) were added, and the mixture was subjected to ion exchange treatment at room temperature for 4 hours. The ion-exchange resins were separated, and a solution of compound (C) was obtained. The obtained compound (C) corresponded to Formula (C-1), and the weight average molecular weight Mw measured by GPC in terms of polystyrene was 1,700 [0100] wherein Formula (C-1) is the following:
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[0075] which is equivalent to compound having a structure represented by Formula (100) of instant claims 1, 2, and 9 when L0 is an alkenylene group having 2 carbon atoms, T0 is a single bond, Ar is a substituted aromatic ring having 6 carbon atoms, n is 1 where R0 is as monovalent organic group.
With regard to claims 17-19, Sakamoto et al. teaches in Examples 1 to 3, the compositions for coating a stepped substrate prepared in Production Examples 1 to 3, respectively, were each applied to a silicon wafer using a spinner (spin coating). Each silicon wafer was heated on a hot plate at 215° C. for 1 minute to form a coating film with a thickness of 0.20 μm (resist underlayer film). This stepped substrate-coating film was irradiated with ultraviolet light of 500 mJ/cm.sup.2 using an ultraviolet light irradiation device manufactured by EYE GRAPHICS CO., LTD. (super-high pressure mercury lamp 1 kW, illuminance at 313 nm: 20.5 mW/cm.sup.2) [0109], in Examples 4 to 6, the compositions for coating a stepped substrate prepared in Production Examples 1 to 3, respectively, were each applied to a silicon wafer, and heated on a hot plate at 215° C. for 1 minute, to form a stepped substrate-coating film [0112], and a resist film is applied to an upper layer of the stepped substrate-coating film (flattened film) obtained from the composition for coating a stepped substrate of the present invention, exposed, and developed to form a resist pattern, and the substrate is processed by dry etching through the resist pattern using an etching gas or the like [0116].
Claim 1 recites “A resist underlayer film-forming composition” which refers to the intended use of the composition. It has been held that a recitation with respect to the manner in which a claimed composition is intended to be used does not differentiate the claimed composition from a prior art composition satisfying the claimed structural limitations. Ex Parte Masham, 2, USPQ2d 1647 (1987). This recitation of the composition is drawn to intended use; therefore, this limitation does not add any patentable weight to the claim (MPEP 2106). Thus, the composition of Sakamoto et al. is the same as instantly claimed.
Claims 1, 2, 9, and 15-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Neef et al. (U.S. 2004/0110089).
Neef et al. teaches in Example 5, α-Cyano-4-Hydroxycinnamic Acid Grafted to Trimethylolpropane Triglycidyl Ether: 1. Preparation of Mother Liquor: Trimethylolpropane triglycidyl ether (6.05 g), α-cyano-4-hydroxycinnamic acid (11.35 g), benzyltriethylammonium chloride (0.34 g), and propylene glycol n-propyl ether (156.6 g) were added to a round bottom flask. A nitrogen atmosphere was established, and the reaction was heated at 120°C for 16 hours. The solution was allowed to cool and was then bottled. 2. Preparation of Anti-Reflective Coating: The mother liquor (20 g) prepared in Part 1 of this example was blended with Powderlink® 1174 (0.50 g) (crosslinking agent), p-toluene sulfonic acid (0.06 g) (acid generator), propylene glycol n-propyl ether (10.84 g), and ethyl lactate (28.84 g). The solution was filtered through a 0.1-.mu.m PTFE filter prior to use [0048-0051] (claims 1, 15, and 16) wherein α-Cyano-4-Hydroxycinnamic Acid Grafted to Trimethylolpropane Triglycidyl Ether is equivalent to compound having a structure represented by Formula (100) of instant claims 1, 2, and 9 when L0 is a substituted alkenylene group having 2 carbon atoms, T0 is a single bond, Ar is a substituted aromatic ring having 6 carbon atoms, n is 1 where R0 is a hydroxy group.
With regard to claim 17, Neef et al. teaches each formulation was applied to a 4-inch silicon wafer and baked at 205.degree. C. for seconds [0054].
With regard to claim 18, Neef et al. teaches each formulation was applied to A 4-inch silicon wafer and baked at 205°C. for 60 seconds. The film thickness was measured with an ellipsometer. A commercially available photoresist was applied to the film, and a post-application bake (130°C. for 90 seconds) was performed. The resist was exposed to light followed by a post-exposure bake (130°C. for 90 seconds). After removal of the photoresist with 0.26 N tetramethylammonium hydroxide (TMAH) developer, the film thickness was remeasured [0056].
With regard to claim 19, Neef et al. teaches the method of applying the inventive anti-reflective compositions to a substrate (e.g., Si, Al, W, WSi, GaAs, SiGe, Ge, Ta, and TaN wafers) simply comprises applying a quantity of a composition hereof to the substrate surface (either a planar surface or one comprising vias or holes formed therein) by any conventional application method, including spin-coating. The layer should then be heated to at least about the crosslinking temperature of the composition (e.g., about 150-205°C) so as to cure or harden the layer having a thickness of anywhere from about 100-5,000 Ǻ where the thickness is defined as the average of 5 measurements taken by an ellipsometer. A photoresist can then be applied to the cured material, followed by exposing, developing, and etching of the photoresist [0023].
Claim 1 recites “A resist underlayer film-forming composition” which refers to the intended use of the composition. It has been held that a recitation with respect to the manner in which a claimed composition is intended to be used does not differentiate the claimed composition from a prior art composition satisfying the claimed structural limitations. Ex Parte Masham, 2, USPQ2d 1647 (1987). This recitation of the composition is drawn to intended use; therefore, this limitation does not add any patentable weight to the claim (MPEP 2106). Thus, the composition of Neef et al. is the same as instantly claimed.
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.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Ito et al. (U.S. 10,570,248).
With regard to claim 3, Ito et al. teaches the above compound PA6 having a methoxy group as the substituent instead of the instantly claimed formula (101) having a nitro group.
However, Ito et al. teaches the above compound PA6 is a specific example of a compound obtained by reacting a cinnamic acid compound of Formula (1) below with a compound having at least one epoxy group in one molecule [col 4 lines 45-51]:
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[col 4 line 52] wherein R1, R2, R3, R4, and R5 are each independently a substituent selected from a hydrogen atom, a halogen atom, a C1-6 alkyl, a C1-6 haloalkyl, a C1-6 alkoxy, a C1-6 haloalkoxy, a C3-8 cycloalkyl, a C3-8 halocycloalkyl, a C2-6 alkenyl, a C2-6 haloalkenyl, a C3-8 cycloalkenyl, a C3-8 halocycloalkenyl, a C2-6 alkynyl, a C2-6 haloalkynyl, a (C1-6 alkyl) carbonyl, a (C1-6 haloalkyl) carbonyl, a (C1-6 alkoxy) carbonyl, a (C1-6 haloalkoxy) carbonyl, a (C1-6 alkylamino) carbonyl, a (C1-6 haloalkyl) aminocarbonyl, a di(C1-6 alkyl) aminocarbonyl, cyano, and nitro [col 4 line 63-col 5 line 5] such that when at least of R1 to R5 is nitro, it is equivalent to the compound represented by formula (101) of instant claim 3 when R1 is a group having a reactivity with an epoxy group (carboxy), L1 is an alkenylene group having 2 carbon atoms, Ar is a substituted aromatic ring having 6 carbon atoms, and n is 1 to 3. Ito et al. also teaches the present invention will be described in further detail with reference to Examples, but the present invention is not limited to these Examples [col 37 lines 38-30] and an object of the present invention is to provide a cured-film formation composition that is suitable to form a cured film having excellent liquid-crystal orientation properties and excellent light transmission properties [col 2 lines 46-48].
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 Ito et al. to include additional compositions having compounds such as one having a nitro substituent and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention in order to achieve optimum liquid-crystal orientation properties and light transmission properties.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Sakamoto et al. (U.S. 2018/0086886).
With regard to claim 3, Sakamoto et al. teaches the above compound (C-1) having a methoxy group as the substituent instead of the instantly claimed formula (101) having a nitro group.
However, Sakamoto et al. teaches the compound (C-1) is a specific example of a compound having a partial structure of formula (1) which is a reaction product of an epoxy group-containing compound (A) and cinnamic acid (B) having the partial structure of Formula (1) [0018] wherein a specific example of (B) includes the following formulas (B-6) and (B-12):
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[0073] wherein formula (B-12) is used to make compound (C-1) in Production Example 1 and formula (B-6) is equivalent to the compound represented by formula (101) of instant claim 3 when R1 is a group having a reactivity with an epoxy group (carboxy), L1 is an alkenylene group having 2 carbon atoms, Ar is a substituted aromatic ring having 6 carbon atoms, and n is 1. Sakamoto et al. also teaches the present invention provides a composition for coating a stepped substrate that has high filling properties of a pattern, and is capable of forming a coating film that does not cause degassing and heat shrinkage, and is used to form a coating film having flattening properties on the substrate [0016].
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 Sakamoto et al. to include additional compositions having compounds such as one having a nitro substituent and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention in order to achieve a coating film that does not cause degassing and heat shrinkage.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Hashimoto et al. (WO2018052130).
With regard to claim 15, Hashimoto et al. teaches the above composition in Example 5 but does not teach an acid generator.
However, Hashimoto et al. teaches The protective film-forming composition of the present invention may contain an organic acid as an optional component. Examples of the organic acid include sulfonic acid compounds and carboxylic acid compounds, such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonate, pyridinium trifluoromethanesulfonate, salicylic acid, camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid, 4-phenolsulfonic acid, methyl 4-phenolsulfonate, benzenedisulfonic acid, 1-naphthalenesulfonic acid, citric acid, and benzoic acid [col 22 lines 18-29] which are equivalent to an acid generator of instant claim 15. Hashimoto et al. teaches it is an object of the present invention to provide a novel composition for forming a protective film having resistance to aqueous hydrogen peroxide solutions and a pattern formation method using the protective film [col 1 lines 58-62].
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 Hashimoto et al. to include additional compounds such as an organic acid and arrive at the instant claims through routine experimentation of combining equally suitable components for the sought invention in order to obtain a film resistant to aqueous hydrogen peroxide solutions.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Endo et al. (U.S. 2018/0181001).
With regard to claim 3, Endo et al. teaches the above compound (3-4) having a methoxy group as the substituent instead of the instantly claimed formula (101) having a nitro group.
However, Endo et al. teaches compound (3-4) is a specific example of an epoxy adduct (C) obtained by reacting an epoxy group-containing compound (A) with an epoxy adduct-forming compound (B), wherein one or both of the epoxy group-containing compound (A) and the epoxy adduct-forming compound (B) contain an optionally branched alkyl group having a carbon atom number of three or more [0033] wherein examples of the epoxy group-containing compound (A) includes the following formula (1-6):
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[0041] and as the epoxy adduct-forming compound (B) used in the present invention, at least one compound selected from the group consisting of carboxylic acid (B1), carboxylic anhydride (B2), a phenol compound (B3), a hydroxyl group-containing compound (B4), a thiol compound (B5), an amino compound (B6), and an imide compound (B7) can be used [0061], as the carboxylic acid (B1), a compound of formula (2) can be used. In formula (2), R1 is an optionally branched alkyl group having a carbon atom number of 3 to 19, Ar1 is a C6-40 arylene group optionally having a substituent, n5 and n6 are each an integer of 0 or 1, n7 is an integer of 1, and n8 is an integer of 1 or 2 [0064], examples of the C6-40 arylene group include arylene groups derived from the following aryl groups or substituted aryl groups. Further, hydrogen atoms may be partially substituted with a hydroxyl group, a nitro group, a cyano group, or a halogen atom (fluorine, chlorine, bromine, iodine) [0066], and examples of the aryl groups or substituted aryl groups include p-nitrophenyl group [0066] such that when the compound (3-4) is additionally substituted with a nitro group it is equivalent to the compound represented by formula (101) of instant claim 3 when R1 is a group having a reactivity with an epoxy group (carboxy), T0 is a single bond, L0 is an ester group, Ar is a substituted aromatic ring having 6 carbon atoms, and n is 1. Endo et al. also teaches an object of the present invention is to improve the filling properties of the pattern during baking by enhancing the thermal reflow properties of the polymer. Specifically, in order to enhance the thermal reflow properties of the polymer, a long-chain alkyl group capable of decreasing the glass transition temperature of the polymer is introduced. Thus, a resist underlayer film-forming composition in which a decrease in viscosity is sufficiently expressed before a crosslinking reaction during baking starts and a coating film having high flattening properties is formed on a substrate is provided [0009].
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 Endo et al. to include additional compositions having compounds such as one having a nitro substituent and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention in order to improve the filling properties of the pattern during baking.
Claims 3 and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Neef et al. (U.S. 2004/0110089).
With regard to claims 3 and 8, Neef et al. teaches the above compound α-Cyano-4-Hydroxycinnamic Acid Grafted to Trimethylolpropane Triglycidyl Ether in which the epoxy compound has a heterocyclic structure and having a hydroxy group as a substituent instead of the instantly claimed formula (101) having a nitro group.
However, Neef et al. teaches the above compound is a specific example of a compound comprising at least two epoxy moieties which are each individually bonded with respective light attenuating moieties [0010] examples of the preferred precursor compound including at least toe epoxy moieties includes the following:
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[0010] and the light attenuating moieties utilized preferably comprise a chromophore having carboxylic acid portion for bonding with an epoxy [0011] including the following:
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[0011] where each of R, X, and/or Y is individually selected from the group consisting of alkyl (preferably C1-C12, and more preferably C1-C8), aryl (preferably C4-C20, and more preferably C6-C14), ether, cyano, nitro, sulfonyl, sulfone, sulfonate, chloro, fluoro, bromo, iodo, carbonyl, amino, and thioether groups [0012] such that when the hydroxy group is replaced by a nitro group of the compound of Example 5 it is equivalent to a compound having a structure represented by Formula (100) of instant claim 1, specifically a compound that is the reaction product of a heterocyclic epoxy group-containing compound and a compound represented by formula (101) of instant claims 3 and 8 when L0 is an alkenylene group having 2 carbon atoms, T0 is a single bond, Ar is a substituted aromatic ring having 6 carbon atoms, and n is 1. Neef et al. also teaches the following examples set forth preferred methods in accordance with the invention. It is to be understood, however, that these examples are provided by way of illustration and nothing therein should be taken as a limitation upon the overall scope of the invention [0031] and the small molecule anti-reflective coatings have high etching rates and good via fill properties. Photolithographic processes carried out with the inventive material result in freestanding, 110-nm profiles [abstract].
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 Neef et al. to include additional compositions having compounds such as one having a nitro substituent and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention in order to achieve high etch rates and good via fill properties.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. JPH11279523, U.S. 2009/0117493, U.S. 7,846,638, U.S. 2013/0280656, U.S. 2016/0336189, U.S. 2017/0183531, U.S. 2018/0011405, U.S. 2016/0284614, U.S. 2019/0163064, WO2018012253 (U.S. 2020/0201183), U.S. 2021/0181637, and U.S. 2022/0163890.
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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/Anna Malloy/Examiner, Art Unit 1737
/KEITH WALKER/Supervisory Patent Examiner, Art Unit 1735
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