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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 12/24/2025 has been entered.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Response to Amendment
Applicant’s Amendment filed 12/24/2025 has been entered and is considered. Claims 1, 5-7, 9-13, 14, 15, and 18 have been amended. No new matter has been added with these amendments.
Response to Arguments
Applicant’s Amendments to the claims have substantially altered the scope thereof so as to render the prior art used in the most recent Final Rejection moot. As such, all rejections furnished in the prior Final Rejection are hereby withdrawn.
After further search and consideration, the Examiner makes new grounds of rejection over the claims as detailed in the body of the office action below.
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.
(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.
As a matter of claim interpretation – Applicant has claimed a compound in the independent claims 1, 9, 10, 11, and 14 , and does not further state any further compositional limits in dependent claims until claims 16-29. As such, any prior art instance of a compound reading upon the claims reciting a compound will be considered anticipatory regardless of the field of prior art.
Claim(s) 1,2, 4, 5, 6, 12, 13, and 19-23 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Varchi et al (Direct Preparation of polyfunctional amino-substituted arylmagnesium reagents via and iodine-magnesium exchange reaction, RSC, 14th January 2003)
Regarding claim 1 and 13, Varchi discloses a reaction scheme for producing arylmagnesium reagents, and reaction products of these arylmagnesium reagents with electrophiles (Abstract, Table 1).
Table 1 details the following compounds. Relevant examples have been circled by the examiner:
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The above compounds 3b, 3d, 3g, and 3k meet the limitations of the claim where:
Ring A is a phenyl ring (C6 aromatic)
Ra is H or Bu (organic group having 4 carbons),
Rb is H, Ph (organic group having 6 carbons) or CO2Et (organic group having 3 carbons and a substituent)
Rc is H
X is I, L1 is a single bond (claim 13), and m is 1
Subscript n is 2
One Y is an amino group
Another Y is a CO2Et ester group
Subscript r is 0, Z is not present
Regarding Claim 2 and claim 12– the amino group on the compounds referenced above regarding claim 1 is hydrophilic and the ester group CO2Et present on the compounds is acid-decomposable.
Regarding Claim 4 – compound 3g meets the limitations of the claim where the vinyl group has no further substituents (Ra-Rc are each H)
Regarding Claim 5 and 6, the compounds 3b, 3d, and 3k meet the limitations of the claim for where:
At least one of Ra1, Rb1, and Rc1 is substituted by a halogen or an organic group having 1-60 carbons and optionally having a substituent.
The sum of subscripts n+r is 2 (2 +0 = 2)
Regarding Claim 7, the above compounds feature an ethyl ester functionality, meeting the limitations of the claim where L2 is a carboxyl group and R2 is an ethyl group
Regarding Claims 19-23, the reaction scheme described in Scheme 1 does not include a reagent using peroxide, K, Mn, Al, Si, or Li, or a phosphorus-containing compound, or maleic acid. Similarly, the example procedure for producing a compound (3g) does not describe components meeting the limitations of claims 19-23. As these compounds are described as being present in a range of 10ppm or less (the lower bound here being 0ppm or “not present”), these compounds when dissolved in solvent as described in the Notes and References during purification constitute compositions meeting the limitations of the claims, as none of the impurities referenced in the claims are present.
Claim(s) 9 and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Curran et al (Evidence that Palladium(0)-promoted Cyclizations of Unsaturated a-Iodocarbonyls Occur by and Atom Transfer Mechanism, Tetrahedron Letters, Vol 31, pp 933-936, 1990)
Regarding Claim 9 and 11, Curran et al disclose a reaction mechanism and products derived therefrom regarding the isomerization of iodocarbonyl compounds using a palladium catalyst. (Abstract, Eq1). Additionally a ditin reaction is also disclosed (Eq4). The ditin reaction is as follows:
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The product in yellow (right) meets the limitations of the claim where, when E is CO2Me:
Ra-Rc are each H
Ring A is a C6 alicyclic ring (cyclohexyl ring)
Subscript p is 1
Subscript r is 0
Subscript n is 2
Y is CO2Me (ester)
Subscript m is 1
L1 is a single bond
X is I
The sum of m and n is 3
Claim 10 is rejected under 35 U.S.C. 102(a)(1)as being anticipated by Kiel et al (Jörg-Michael Keil, Werner Massa, Ralf Riedel, Gunther Seitz, Sigrid Wocadlo, [4+2]-cycloaddition von tetrachlorcyclopropen an 2- und 3-vinylhetarene: Neue [6+4]- und [6+6]-cyclodimerisierungen als folgereaktionen, Tetrahedron Letters, Volume 35, Issue 43, 1994, Pages 7923-7926,)
Regarding Claim 10, Kiel discloses a chemical substrate and a method of transforming such using a cycloaddition reaction.
Kiel discloses the following compound 14 in the reaction schematic:
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Where R is H, Cl, or Br.
The substituted vinylthiophene of the reference meets the limitations of the claim where:
A is a heterocyclic structure having 4 or 5 carbon atoms (thiophene – 4 carbons)
Ra-Rc are each H
Subscript p is 1
Subscript m is 1
L1 is a single bond
X1 is Br or Cl
Subscript r is an integer of 0
Subscript n is 0
Claim(s) 14 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Bo et al (CN106633648A, published 05/0/2017).
Regarding Claim 14, Bo discloses an ion-resistant material that can be used as a filler in a copper clad laminate.
In preparation of a material, Bo synthesizes the following compound at [0020] and [0044] ([0039 in the CN document):
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This biphenyl compound meets the limitations of the claim where:
A is a phenyl ring having 6 carbons
Subscript p is 1
Ra is CH3
Subscript m is 1
L1 is a single bond
X is a phenyl ring with an I substituted thereupon
Subscript r is 0
Subscript n is 0
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(s) 1, 2, 4-7, 11-13, 19-24, and 26-29 are rejected under 35 U.S.C. 103 as being unpatentable over Fukushima et al (US 2019007399 A1, published 03/14/2019).
Regarding claims 1, 2, 4-7, 11-13, 19-24, and 26-29, Fukushima discloses a monomer, polymer derived therefrom, resist composition, and patterning process, where the monomer is bounded by the formula (A):
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Where X is a single bond, ether, ester, or amide, Ra is a C1-C20 monovalent hydrocarbon group that may have any constituent methylene group replaced by an ether or carbonyl moeity, Rb is H or an acid labile group, X is a halogen, n is an integer of 1-4, m is an integer of 0-3, and RA is H, Me, or CF3 (Abstract, [0015]-[0021], where X is preferably iodine, and [0044]-[0063]). Example embodiments of the monomer are depicted in [0052] – however it should be noted that examples do not disparage the general teachings of a reference.
Fukushima does not disclose an experimental embodiment of the monomer. This limitation is met by the general disclosure of the reference.
Fukushima’s disclosed monomer reads upon the claimed invention of claim 1 for where:
Subscript p is 1, and Rb1-Rc1 are each hydrogen and where Ra1 may be a H, methyl group (C1 organic group) or a CF3 group (C1 organic group having substituent)
Subscript m is 1-4, X is I, and L1 is a single bond (claim 13) (reference X, subscript n)
A person of ordinary skill in the art would be able to immediately envision Iodine from the small genus of “Halogen” which comprises only 4 members in practical applications.
Subscript n is 2-4,
one instance of Y is an alkoxy group (-ORb on the reference structure)
At least one other instance of Y is an ester when two subsequent methylenes in the reference Ra’s C3-C20 embodiments are replaced by a carbonyl group and then an ether bond, the resulting functional group is an ester group R*–(C=O) -O-R**, where * and ** denote bonding points in the substructure (claim 2 and 12 – esters are acid-decomposable)
Claim 7 – L2 is the C(=O)O group, R2 is the remaining C2-C18 hydrocarbon group, which as described in [0046]-[0048] may be an alkyl or cycloalkyl group such as adamantyl or butyl
Subscript r is 0
The sum of subscripts r and n is 2 or more (claim 5 and 6)
A is a phenyl group (C6 organic aromatic ring group)
The monomer of Fukushima is incorporated into a polymer as described from [0064]-[0110] (claim 24)
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention in view of the teachings of the reference - using the substantially similar chemical formula to arrive at compounds that are expected to behave similarly to those claimed due to the chemical similarities thereof.
Regarding Claim 18 in [0080] subunits (c) are discussed, where these units include acrylate and methacrylate esters (and meth/acrylic acid), lactone-bearing subunits, as well as carboxyl, hydroxyl, thiocarbonate, carbonate, cyano, and amide units. Exemplary units include para/meta-hydroxystyrene and hydroxyvinylnapthalene, as well as the styrenic ester compound bearing a lactone group shown below:
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This unit meets the limitations of claim 18 where:
Ra is H, Me, or CF3
Rb-Rc are each H
Subscript p is 1
Subscript r is 0
Subscript m’ is 0
Subscript n is 1
Y is an ester group
The general disclosure does not specifically state a percentage inclusion of this monomer into the polymer of the reference.
This limitation is met elsewhere in the reference.
In the Examples, the polymer 2-7 ([0201]) comprises p-hydroxy styrene, which is incorporated in ~8% by mass of the polymer. As p-hydroxystyrene is presented as a subunit (c) in [0080] alongside the above styrenic ester subunit, the reference considers these subunits to be alternatives to one another and thus expected to behave similarly.
The substitution of a component for an art-recognized alternative is prima-facie obvious – a person of ordinary skill in the art would have found it obvious to arrive at the claimed invention from the disclosure. Such an individual would naturally consider that as the art considers these two units to be functionally equivalent by their presentation together they would be interchangeable, and thus consider incorporating the styrenic ester subunit detailed above in 8 mass% into a polymer to be an obvious substitution of one component for another with expectation of similar results
Regarding Claims 19-23, the compositions described in the examples or in the general disclosure of the reference do not make mention of K impurities, peroxides, Mn/Al/Si/Li impurities, phosphorus-containing compounds, or maleic acid in the final resist product. As such, these compositions (See [0184]-[0233] and Tables 1 and 2) are interpreted as having 0ppm of these components – reading upon all the claims for where these claims delimit N ppm or less, where N is the upper numerical bound. “Or less” includes 0 ppm.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention in view of the teachings of the reference - using the substantially similar chemical formula to arrive at compounds that are expected to behave similarly to those claimed due to the chemical similarities thereof.
Regarding Claims 26-29, The polymers of the disclosure are used in formulating a resist and the resist composition is used in pattern formation as described in [0174]. The resist compositions comprises a base resin (the polymer described regarding claim 24 using monomers of claim 1), an acid generator (claim 27), an organic solvent, and a base compound (claim 27). The composition is coated onto a substrate and baked to form a film (claim 26). After film formation, the film is exposed to EUV radiation through a mask, then post-exposure baked, then developed using a basic TMAH solution (claim 28 and 29 – claim 29 does not identify positive limitations beyond those in claim 28 “insulating film formation method” is interpreted as “intended use” ). Other types of radiation are recited in the general disclosure – EB, DUV, and UV radiation may be used ([0174]).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention in view of the generally disclosed composition and method steps, using a known product as part of a known patterning method to arrive at the predictable result of a patterned film layer.
Claim 25 is rejected under 35 U.S.C. 103 as being unpatentable over Fukushima et al (US 20190079399 A1, published 03/14/2019) as applied to claims 1 and 24 above, and further in view of Qin et al (CN108628101A, published 10/09/2018).
Regarding Claim 25, Fukushima discloses the limitations of the claim as described above regarding claims 1 and 24.
Fukushima broadly discloses a polymer resin having acrylate and methacrylate monomers (in addition to the monomer of claim 1), specifically from [0069]-[0081], but fails to disclose variants of these units where the acrylates are substituted with a hydroxyl group or halogen along the backbone carbon to form a haloacrylate or hydroxyacrylate.
This limitations are met by Qin.
Qin discloses an electron-beam photoresist comprising side-chain substituted halogen atoms in the resist polymer. The halogenated acrylate polymer is preferably represented by formula (I) or formula (II):
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Where X is F, Cl, Br, or I; R1 is C1-C11 alkyl and may be substituted; R2 is C6-C20 aryl; R3 is H or methyl.
The subunit comprising R1 meets the limitations of the claimed formula C6 for where:
Xc61 is a halogen
Rc61 is a C1-C11 alkyl group
A photoacid generator is also included ([0025]), such as triphenylsulfonium triflate.
A solvent is also present, described in [0036], such as PGMEA and anisole.
The resist composition is described to having improved exposure efficiency in an EB exposure process ([0038]).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by incorporating the haloacrylate monomers of Qin into the polymer and resist composition of Fukushima to improve the electron-beam exposure performance of the resultant composition in patterning.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Saito et al (US 20150353826 A1, published 12/10/2015).
Regarding Claim 15, Saito discloses a liquid crystal composition having negative dielectric anisotropy as imparted by specific compounds therein. These compounds may include those conforming to the general formula (1) as described in [0010] and [0021]:
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Where R1 and R2 are independent a C1-C12 alkyl/alkoxy, alkenyl having 2-12 carbons, or C1-C12 alkyl wherein a fluorine or chlorine is substituting at least one hydrogen. Rings A and B are independently 1,4 cyclohexane, 1,4-cyclohexene, tetrahydropyran-2-5-diyl, 1,4-phenylene or a phenylene wherein a hydrogen has been replaced with chlorine or fluorine, 2,6-naphthalene or a fluorinated/chlorinated variant, chroman-2,6-diyl or a fluorinated/chlorinated variant. Z1 and Z2 are independently a single bond, ethylene, carbonyloxy, or methyleneoxy. Subscripts a and b are independently an integer from 03-, and a+b is less than or equal to 3.
At [0022], the following specific formulas are given:
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R1 and R2 are as defined above. In the experimental examples, R1 and R2 as terminal groups may specifically be methyl, propyl, and vinyl groups (demarcated in Table 3 as -n- here n=1, 3, or another integer, and as -V, respectively).
The above formulas meet the limitations of claim 15 for where:
A is a C6 aromatic ring or C6 aliphatic ring
Subscript p is 1
Ra-Rc are H (R1 is vinyl (C2 alkenyl))
Subscript m is 1
L1 is a single bond
X is a C6-C10 unsaturated alicyclic structure having 4 F (a C6 ring with 4F and a C1-C4 alkyl substitution thereupon)
Subscripts n and r are each 0
As more specific examples, from the general disclosure of the reference the following compounds can be constructed, where R1 is vinyl, and R2 is methyl or propyl, where the above limitations are met and the alicyclic structure of X is a C7 or C10 structure having 4 fluorines thereupon.
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A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of the reference, which discloses a set of substantially similar compounds - a person of ordinary skill in the art would consider these compounds as a viable component of the liquid crystal composition of Saito due to their chemical similarity and as such exhibiting favorable optical properties.
Claims 16 and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Fukushima et al (US 2019007399 A1, published 03/14/2019) as applied to claims 1 above, and further in view of Kyohei et al (WO 2019045107 A1, published 03/07/2019, US 20210173309 A1 used in lieu of translation.
Regarding claims 16 and 17, Fukushima discloses the limitations of the claims as described above regarding claim 1. Fukushima discloses a monomer, polymer derived therefrom, resist composition, and patterning process, where the monomer is bounded by the formula (A):
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Where X is a single bond, ether, ester, or amide, Ra is a C1-C20 monovalent hydrocarbon group that may be ester-substituted, Rb is H or an acid labile group, X is a halogen, n is an integer of 1-4, m is an integer of 0-3, and RA is H, Me, or CF3 (Abstract, [0015]-[0021], where X is preferably iodine, and [0044]-[0063]). Example embodiments of the monomer are depicted in [0052]. As Kyohei discloses that X1 may be a single bond, ester linkage, ether linkage, or amide linkage, these options and their derived compounds are considered alternatives to each other by the art - thus expected to function similarly.
Fukushima however does not disclose an experimental embodiment comprising a compound meeting the limitations of claim 16 and 17 where the compound 1C1 and 1D are present in an amount of 1ppm to 10mass% relative to the compound of claim 1.
This limitation is met by Kyohei.
Kyohei discloses a method of forming a reversed pattern including a step of forming a resist film on a substrate using a photosensitive composition, wherein the photosensitive composition comprises a polymer and an acid generator.
Kyohei discloses a wide variety of monomers as part of a taught composition used to synthesize the polymer of the resist composition. These monomers are broadly taught from [0062]-[0264]. Specific monomer embodiments included in the polymer are those represented in formula (B) in [0233], where the monomer (B) is represented by
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Where Rb1-Rb4 each independent represent a hydrogen atom or an organic group, such as in the repeating units:
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Where R’ is an aryl group, aralkyl group, which may have a substituent such as a halogen, ester, or other group described in [0238]. The monomer units outlined herein are not explicitly defined by their mass% in the total polymer – however, the experimental examples contain many compositional examples wherein monomers are present in 10% by mass (see Table 2).
A person of ordinary skill in the art would recognize that the ester functionalities of Kyohei are considered analogous to those of Fukushima – and Fukushima acknowledges that ester and styrene monomers are analogous. As such, a person of ordinary skill in the art would have found it obvious to arrive at a structure where the ester linkage in Kyohei is a single bond as taught by Fukushima.
A person of ordinary skill in the art would recognize the chemical similarity between the monomers recited above and those of the claimed invention, being vinyl monomers having aryl substituents having halogens thereupon – chemical similarity begets a similarity of properties (See MPEP 2144.09). Similarly, the compound of claim 17 is a biaryl compound having halogenated aryl groups and is similar in structure to that of claim 16 - though not polymerizable, a person of ordinary skill would recognize it would bear similar optical properties. The resist composition of Kyohei is specifically directed to EUV exposure, as is that of Fukushima, where the halogenated aryl groups of the resist components aid in the sensitivity of the resist.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by way of chemical similarity, wherein the chemical similarity of the monomer(s) recited by the claim are incorporated into the composition of Fukushima and Kyohei at 10mass% as a substitution of an existing monomer with an expectation that the two polymer synthesis compositions would behave similarly and thus arrive at a polymer and additive capable of use in a photoresist composition having high patterning resolution.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANDREW PRESTON TRAYWICK whose telephone number is (571)272-2982. The examiner can normally be reached Monday - Friday 8-5.
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/A.P.T./Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734