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 .
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 07/08/2026 is being considered by the examiner.
Response to Amendment
Applicant’s Amendment filed 05/19/2026 has been considered and is entered with this action. Claims 1, 9-11, 14, and 15 have been amended. New claims 55 and 56 have been added.
Response to Arguments
Applicant’s Amendments to the claims and arguments based thereon have altered the scope of the claims so as to render the prior art used in the most recent Non-final Rejection moot. As such, all rejections furnished in the prior Non-Final Rejection are hereby withdrawn.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. Applicants amendments necessitated the new grounds of rejection.
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, 10, 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 1 is rejected under 35 U.S.C. 102(a)(1)as being anticipated by Gagnier et al ( Steve V. Gagnier, Richard C. Larock; Palladium-Catalyzed Carbonylative Cyclization of Unsaturated Aryl Iodides and Dienyl Triflates, Iodides, and Bromides to Indanones and 2-Cyclopentenones. Journal American Chemical Society 23 April 2003; 125 (16): 4804–4807)
Regarding claim 1, Gagnier discloses a palladium catalyzed cyclization reaction using aryl iodide and dienyl triflates/iodides/bromides as substrates to arrive at indanones and 2-cyclopentanones (Introduction).
At Table 1, experimental examples provided include the following chemical substrates acted upon in the reaction (See page 2 of the attached publication, publication page 4805):
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The compounds 13 and 15 meet the limitations of the claim where:
Ra-Rc are each H
Subscript p is 1
The group is a vinyl group (claim 4)
L1 is a single bond (claim 13), X is I
Subscript m is 1
Subscript n is 2 or 3, each Y is a methoxy group (alkoxy)
Methoxy groups are decomposable groups by action of acid (claim 2, 12)
The sum of subscript m+n is 3 or 4
Subscript r is 0
The sum of subscripts n+r is 2 or 3 (claim 6)
Regarding claims 19-23, the compounds 13 and 15 are dissolved in DMF alongside a palladium catalyst and pyridine, constituting a composition (see note a at the bottom of Table 1). The reference makes no mention of impurities comprising K, Mn, Al, Si, and/or Li (claims 19 and 21). The reference makes no mention of peroxides, maleic acid, or phosphorus-containing compounds (claims 20, 22, and 23). This lack of mentions are interpreted that these impurities/components are not present and therefor the composition meets the limitations of these claims.
Claim 10 is rejected under 35 U.S.C. 102(a)(1)as being anticipated by Das et al (Sudipto Das, Suvendu Samanta, Shounak Ray, Papu Biswas; 3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine capped Pd(0) nanoparticles: a catalyst for copper-free Sonogashira coupling of aryl halides in aqueous medium. RSC Adv. 2015; 5 (92): 75263–75267.)
Regarding Claim 10, Das discloses a palladium nanoparticle catalyst for sonogashira coupling of aryl halides, where in Scheme 3 an aryl iodide substrate is used as an organic substrate for the reaction and the product is further hydrolyzed:
[AltContent: rect]
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The circled product 4 is the result of the corresponding heteroaryl iodide reactant being coupled and then hydrolyzed to remove the trimethylsilyl group – see Scheme 3 and caption on Table. A sonogashira coupling was performed using the heteroaryl iodide after which the trimethylsilyl group was removed, wherein the fragment inside the inner circle is bears the heteroaryl structure of the reactant (sans iodide, which is removed during the coupling). The corresponding iodide bears the following structure:
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This component reads upon the claim wherein:
Ra-Rc are each H
Subscript p is 1
A is a heterocycle having 5 carbon atoms
L1 is a single bond, X is I
Subscript m is 1
Subscripts n and r are 0
Claim 14 is rejected under 35 U.S.C. 102(a)(1)as being anticipated by Lee et al (KR 101243612 B1, published 06/28/2013)
Regarding Claim 14, Lee discloses novel furan derivatives and a manufacturing method thereof.
Lee disclsoses at [0131] the synthesis of 2-iodophenyl-3-vinyl-2,5-dihydrofuran:
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This compound meets the limitations of the claim where:
Ra-Rc are each H
A is a dihydrofuran (4-carbon heterocycle)
L1 is a single bond
X is a phenyl group (aryl group) on which an I has been introduced
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 20190079399 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)
The monomer does not meet the limitations of the claim for where the Y group is positioned at least one carbon away from the vinyl group. However, the claimed ring A is an aromatic ring having 6-10 atoms and the reference ring is an aryl ring having 6 atoms. A person having ordinary skill in the art would be able to arrive at or envision the finite number of configurations where the -O-Rb group of the reference is not ortho- to the vinyl group. A 6 membered aryl ring only has 6 positions, only 5 of which are free for further substitution when the ring is vinyl-substituted. Two of these positions are ortho- to the vinyl group, leaving three non-ortho positions. Such a small number of configurations (5 configurations) would naturally be envisaged by a person of ordinary skill in the chemical arts. These configurations are substantially similar in structure (they do not have additional components or moeities) and would nominally be expected to have similar properties and exhibit similar performance due to the chemical similarity (See MPEPE 2144.09.I and .II).
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date by selecting stereoisomeric embodiments to the reference’s styrene derivatives, recognizing that the small number of substitution positions for an on a styrene ring enables immediate envisagement and also that the structural similarity should abet similar performance chemically.
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(s) 9, 11, and 56 are rejected under 35 U.S.C. 103 as being unpatentable over Hayakawa (US 20160355461, published 12/08/2016).
Regarding Claims 9 and 11, Hayakawa teaches a resist composition and a compound for improving the resolution, sensitivity, and line edge roughness (Abstract).
Hayakawa however does not detail an experimental embodiment of a compound meeting the limitations of the claim.
These limitations are met in the general disclosure of the reference.
Hayakawa produces an alicyclic acrylate ester compound (1):
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Where
R1 is a hydrogen or methyl group
R2 and R3 may each independently be a halogen, H, OH, alkyl group having 1-10 carbons, C1-C10 alkoxy, aryloxy, or acyloxy group.
Halogen, in practical use, consists of F, Br, Cl, and I – a person having ordinary skill in the art would immediately envision Iodine or any other of the 4 species in this very small genus.
R4 is a linear or branched alkylene having 2-5 carbons.
The above compound meets the limitations of the claims for where:
Ra may be methyl (C1 organic) or H, Rb-Rc are H
Subscript p is 1
A is an adamantyl group having optional substituents (wherein the substituent(s) is/are the linking group to the vinyl group)
L1 is a single bond, X is an iodine (claim 9) or a halogen (claim 11)
Subscript m is 1
Subscript n is 2
One Y is a hydroxyl group, the other Y is a hydroxyl group or an alkoxy group
The reference further teaches a synthetic method to make the compound for formula (1) at [0028]-[0031] and
Hayakawa incorporates this compound as a monomer into a methacrylic copolymer as described at [0032] and [0059]-[0071], which may be further incorporated into a photoresist resin composition as per [0072]-[0076].
The polymer comprising the monomer above meets the claim limitations of claim 56 where:
Ra may be methyl (C1 organic) or H, Rb-Rc are H
Subscript p is 1
A is an adamantyl group having optional substituents (wherein the substituent(s) is/are the linking group to the vinyl group) (C12-C17 organic group)
L1 is a single bond, X is an iodine
Subscript m is 1
Subscript n is 2
One Y is a hydroxyl group, the other Y is a hydroxyl group or an alkoxy group
At [0024], Hayakawa ascribes an improvement in resist performance metrics such as resolution and line edge roughness, as well as improvements in sensitivity, to resin compositions comprising the repeat unit derived from the compound of formula (1)
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date from the disclosure of the reference by making and then incorporating the taught vinyl adamantyl compound into a photoresist resin composition having improved lithographic performance.
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 Nawrocki et al (US 20150024326 A1).
Regarding Claim 15, Nawrocki teaches photoimageable compositions and processes for fabrication of relief patterns using cured products of the compositions (Abstract).
Nawrocki does not teach a specific experimental example meeting the limitations of the claim.
These limitations are met by the general disclosure of the reference.
Nawrocki’s invention comprises at least one alkali soluble resin (A) or a alkali insoluble resin (B) that becomes soluble upon action by an acid, at least one cationic photoinitiator (C), at least one solvent, and at least one fluorinated compound.
The polymers/resins (A) and (B) are discussed from [0030]-[0053] and may be epoxy resins or resins with methacrylic or styrenic subunits.
Resins (B) according to the formula 8 are depicted below:
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Where the R1 group may be a hydrogen or an acid labile group, and R2 may be a group such as tert-butyl that is also acid labile.
Resins (B) according to formula 9 are generally of the structure below,
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where units 3) and 2) are each styrene derivatives. The subunit 2) bears an R1 functional group, where the R1 may be a substituted C1-C8 alkyl group, or another group recited in [0048]. The reference is not specific to whether the C1-C8 alkyl group is linear/branched/cyclic, but a person having ordinary skill in the art would consider the selection of a branched, cyclic, or linear alkyl group to be a matter of chemical similarity and would be able to envision any number of cyclic (alicyclic) embodiments from the claimed range and formula – the reference further discloses that cyclic embodiments may be formed by the bonding of two of the substituent groups. R4 and R5 may be hydrogen or an C1-C8 substituted or unsubstituted alkyl.
The groups R1-R5 may be further substituted such as with a halogen or another group recited in [0049]. A person having ordinary skill in the art would find it obvious to arrive at iodine from the genus of halogen due to the incredibly small amount of species in the genus.
The subunit 2) of formula 9 (in monomer form) meets the limitations of the claim for where:
Ra-Rc are hydrogens, or Ra is a C1-C8 alkyl group and Rb-Rc are hydrogens
Subscript p is 1
A is a C6 aryl group (phenyl)
L1 is a single bond, X is a C3-C8 cycloalkyl (alicyclic) group substituted with an iodine
Subscript m is 1
Subscripts n and r are 0
The styrene derivative in formula 8 meets the limitations of the claim for where:
Ra-Rc are hydrogens, or Ra is a C1-C8 alkyl group and Rb-Rc are hydrogens
Subscript p is 1
A is a C6 aryl group (phenyl)
L1 is an ether linkage, X is a C3-C8 cycloalkyl (alicyclic) group substituted with an iodine
Subscript m is 1
Subscripts n and r are 0
Nawrocki ascribes useful performance to the resins 8 and 9 in photo imageable compositions at wavelengths of 220-450nm when combined with initiators and photosensitizers ([0051].
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the time of filing in view of the teachings of Nawrocki by incorporating the taught monomer into the resins of the photo imageable composition in order to arrive at a composition displaying improved performance.
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.
Claim 55 is rejected under 35 U.S.C. 103 as being unpatentable over Koyama et al (US 20100297555 A1)
Regarding Claim 55, Koyama is directed to photoresist compositions comprising polymers having monomers with electron-withdrawing groups, wherein the monomers bear lactone groups thereon (Abstract).
Koyama does not disclose a specific experimental embodiment that meets the limitations of the claims.
These limitations are met by the general disclosure of the reference.
The monomer and corresponding polymer of Koyama is as delimited by formula (1) at [0007]-[0010:
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Where:
Ra is a hydrogen, halogen, substituted/unsubstituted alkyl group of 1-6 carbons,
A represents an alkyl group having 1-carbons, O, S, or a null/non-bond
R1 is a substituent bound to the ring and may be a halogen, haloalkyl or alkyl group having 1-6 carbons, C1-C6 hydroxyalkyl or halo hydroxyalkyl that may be protected by a protecting group, carboxyl group that may form a salt, or a substituted oxycarbonyl group
Halogen comprises 4 species that can be immediately envisaged due to the small size of the genus – F, Cl, Br, and I
Subscript m is 0-8
X represents an electron-withdrawing substituent
At [0022], Xs include halogens, acyloxy groups, acetoxy groups, among others
Halogen comprises 4 species that can be immediately envisaged due to the small size of the genus – F, Cl, Br, and I
Subscript n is 1-9
Y is a C1-C6 organic group
Exemplary lactone substituents are presented in chemical formulas 10 and 11 at [0030], and synthetic methods to arrive at the lactone monomer are discussed from [0031]-[0048].
Additional subunits are further presented at Chemical formula 14, with subunits 2a-2d ([0053])
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Wherein in 2c:
Ra is a hydrogen, halogen, or substituted/unsubstituted alkyl group of 1-6 carbons,
Z1 is a C5-C20 alicyclic hydrocarbon ring
The ring may be substituted, such as with halogen atoms ([0055])
Halogen comprises 4 species that can be immediately envisaged due to the small size of the genus – F, Cl, Br, and I
R5 is an alkyl group, hydroxyl group, protected hydroxyl group (ether group), carboxyl group, or protected carboxyl group (ester group).
At least one R5 is a protected carboxyl group -COORc, where Rc is a tertiary hydrocarbon group, tetrahydrofuranyl group, tetrahydropyranyl group, or oxetanyl group
Subscript p is 1-3
The lactone subunit conforming to reference formula (1) meets the limitations of the claimed polymeric subunit where:
Ra is a hydrogen, halogen, substituted/unsubstituted alkyl group of 1-6 carbons
Rb-Rc are H
Subscript p is 1
A represents a C9-C10 alicyclic structure comprising a lactone and a linking group (Reference lactone group where A is C1,O,S, or null; Y is C1 alkyl)
L1 is a single bond, X is a substituent bound to the ring as a halogen
Halogen comprises 4 species that can be immediately envisaged due to the small size of the genus – F, Cl, Br, and I
Subscript m is 1-8
Y is represents an electron-withdrawing substituent (reference X) such as a(n) alkoxycarbonyl (ester) groups or nitro group
Subscript n is 1-9
Subscript r is 0
Additionally and alternatively, the subunit and polymer comprising the subunit 2c meet the limitations of the claim where:
Ra is a hydrogen, halogen, substituted/unsubstituted alkyl group of 1-6 carbons
Rb-Rc are H
Subscript p is 1
A represents a C6-C10 alicyclic structure comprising an alicyclic ring and a linking group (Reference alicyclic ring Z1 having 5-9 carbons and a carboxyl linkage)
L1 is a single bond, X is a substituent bound to the ring as a halogen (the ring Z1 may have at least one substituent that may be a halogen – [0055])
Halogen comprises 4 species that can be immediately envisaged due to the small size of the genus – F, Cl, Br, and I
Subscript m is at least 1
Y is represented by at least one ester, where other Ys may each be one of hydroxyl group, protected hydroxyl group (ether group), carboxyl group, or protected carboxyl group (ester group).
Subscript n is 1-3
Subscript r is 0
Koyama ascribes improved solubility in alkaline developer and therefore finer patterning as a result of lithographic processing the polymer comprising the monomers disclosed ([0020]).
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date in view of the teachings of Koyama and incorporating the taught monomer(s) therein into a resist composition so as to improve the fineness of the resultant pattern arrived at from lithographic processing.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/A.P.T./Examiner, Art Unit 1737
/SALLY A MERKLING/SPE, Art Unit 1738
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