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.
Response to Amendment
Applicant’s Amendment filed 07/16/2026 has been entered and is considered with this action. Claim 1 has been amended.
Response to Arguments
Applicant’s Amendments and arguments based thereon are considered to place the scope of the claims outside that of the art used in the prior rejections. As such, all art rejections furnished in the prior rejection are withdrawn. Applicant’s amendment to remove heteroatoms from the scope of R2 places the scope of the art reference Masunaga outside that of the claims.
Applicant’s Amendment to the claim 1 has overcome the rejection made in view of 35 USC 112(b). This rejection is withdrawn.
After further search and consideration, the Examiner makes a new grounds of rejection over Masuyama et al (JP2019214554A) as set forth in the office action below. Applicant’s amendments necessitated the new grounds of rejection.
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) s 1-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Masuyama et al (JP 2019214554A)
Regarding Claims 1-4, 6, 9-10, and 14 , Masuyama disclsoses a compound, resin, resist composition, and method for producing a resist pattern using the resist composition ([0001]).
Maruyama does not disclose a particular experimental embodiment meeting the totality of the claim limitations - these limitations are met by the general disclosure of the reference.
The reference disclsoses a compound represented by formula 1, where the compound is an unsaturated carboxylic acid ester – this compound is incorporated into a resin ([0005]) that comprises additional structural units. The resin comprises structural units such as those comprising acid-labile subunits, which change the solubility in developer upon action of an acid.
A solvent and an onium salt quencher are also disclosed at [0135], wherein the quencher is a salt that generates an acid weaker than the acid generated by the acid generator (See [0198]-[0200] and Quencher D1, a tris(t-butyl phenyl) sulfonium carboxylate salt at [0223]).
Additional components of the composition include a photoacid generator (claim 9 - see [0140]-[0195], stabilizers and surfactants (claim 10 – [0202]).
The subunit of Formula I is as delimited at [0005]:
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R1 is H or Me
R2 is a C1-C6 alkyl group
R3 is H or a C1-C6 alkyl group
Ar is a divalent aromatic hydrocarbon group that may be further substituted
At [0012], Ar is discussed to be phenylene or naphthalene
When the ring is phenylene, the limitations of claim 2 are met
R4 is a fluorinated C1-C12 alkyl group
This formula meets the limitations of the claimed formula (A1) where, when polymerized into a polymer backbone:
RA is H or Me (Reference R1)
ZA is a single bond
RB and RC are each independently a C1-C6 alkyl group (C1-C6 hydrocarbyl group, Reference R2 and R3)
R1 is a C1-C5 fluorinated alkoxy group (overlapped range of C1-C12 fluorinated alkyl group bonded to the -O- between Ar and R4 as in the reference)
Subscript n1 is an integer of 1
Subscript integer of n2 is 0
Subscript n3 is 0 or 1 (Reference Ar is phenylene or naphthalene)
Examples of the compound (I) include those at [0013], such as but not limited to those reproduced below:
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The resin of Masuyama further comprises subunits such as subunit (a2-A) discussed from [0048]-[0057], where the unit (a2-A) meets the formula:
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Ra50 is a H, halogen, or C1-C6 alkyl or haloalkyl group
Aa50 is a single bond or a divalent linking group *-Xa51-(Aa52-Xa52)nb-,
* is a bond attachment
Aa52 is an alkanediyl group that has 1-6 carbons
Xa51 and Xa52 each independently represent -O-, -CO-O, or -O-CO-
Subscript nb represents 0 or 1
Ra51 is a halogen, hydroxy group, C1-C6 alkyl or alkoxy group, alkyl carbonyl group having 2-4 carbons, alkylcarbonyloxy group having 2-4 carbons, acryloyloxy group, or methacryloyloxy group.
Subscript mb is 0-4
The above formula meets the limitations of claim 1 for where it is present in a resin with the polymerized compound 1 and is a subunit having a phenolic hydroxyl group. The resin further meets the limitations of claim 4 for where:
ZB is a single bond or -C(=O)-O- (Reference Aa50 is a single bond or where *-Xa51-(Aa52-Xa52)nb- corresponds to -O-, -CO-O, when nb=0
R11 is a halogen, C1-C6 alkyl or alkoxy group (claimed hydrocarbyl group or hydrocarbyloxy group), C2-C4 alkyl carbonyl group (claimed hydrocarbylcarbonyl group ) , alkylcarbonyloxy group having 2-4 carbons (claimed hydrocarbylhydrocarbonyloxy group).
Subscript m1 is 1 (1 hydroxyl group is present)
Subscript m2 is 0-4 (mb is 0-4)
The sum of m1 and m2 is 1-5
Further structural units (II) are present in the resin of the reference ([0114]-[0130], such as but not limited to unit (II-2A):
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Where:
XIII3 is a divalent saturated hydrocarbyl group having 1-8 carbons, and methylene groups therein may be replaced by thio, oxy, or carbonyl linkage, and hydrogens therein may be replaced by halogens, C1-C6 alkyl/haloalkyl groups, or hydroxy groups.
RIII3 represents a halogen, C1-C6 alkyl or haloalkyl, or a hydrogen
Subscript z may be 0-6
A plurality of RIII2 and RIII4 may be the same or different and each independently represents H, F, or a C1-C6 perfluoroalkyl group
Qa and Qb each independently represent F or a C1-C6 perfluoroalkyl group.
ZA+ may be an onium cation such as a sulfonium or iodonium cation
The above formula meets the limitations of the claimed formula C2 where
Claimed RA is H, F, Me, or CF3 (Reference teaches halogen, hydrogen, and C1-C6 alkyl or haloalkyl – Me and CF3 are C1 alkyl/haloalkyl groups)
Z3 is a single bond (between the reference’s carbon and -CO-O- group)
Z4 is a -C(=O)-O-Z51 group, where Z51 is a C1-C6 aliphatic hydrocarbylene group (reference’s ester linkage having -CO-O-XIII3, where XIII3 may be a C1-C8 saturated hydrocarbyl group)
L1 is a single bond (between reference XIII3 and the tertiary carbon having either RIII2/RIII4 or Qa/Qb)
RF3 and Rf4 are each independently H, F, or a C1-C6 fluorinated alkyl group (reference teaches F, H, and C1-C6 perfluoroalkyl group)
Rf1 and Rf2 are each independently F or a C1-C6 fluorinated alkyl group (Reference teaches F or C1-C6 perfluoroalkyl group)
A+ is a non-nucleophilic cation (Reference’s ZA+, which is a )
Regarding claim 6, at [0118] the cation of the reference, ZA+ is described as being the same as the cation Z+ as defined for the acid generator (B) at [0180]-[0188], such as but not limited to those depicted below:
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The above cations meet the limitations of claim 6 for where cation-1 as claimed comprises Rct1 to Rct3 where each R is a C6-C14 hydrocarbyl group, and where Rct1 and Rct2 may be bonded together to form a ring with the sulfur atom to which they are attached
Masuyama asserts that when the compound conforming to formula 1 is used in a resist pattern composition, the CDU of the resultant pattern is improved relative to a resist composition that does not use this component ([0004 and [0006]).
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention in view of the disclosure of Masuyama, which teaches a composition displaying improved CDU in the resultant pattern formed from lithographic processing.
Regarding Claim 3, Masuyama does not teach a specific embodiment meeting the claim limitation where RA (corresponding to reference R1 on the compound conforming to formula (I)) is trifluoromethyl.
Masuyama discloses that the R1 group is H or Methyl. However, Masuyama discloses other subunits, such as units (II-2-A) and (a1-4), wherein the carbon alpha to the sidechain is substituted with halogens or alkyl groups that may be halogenated ([0031]). A person having ordinary skill in the art would consider it obvious to substitute taught substituents from one monomer onto another (substituting a CF3 from, for example – II-2-A, in place of a methyl group at R1 of formula (I)), such substituents are chemically similar – both are C1 alkyl groups, and the reference contemplates that both substituents may be used in subunits for a polymer resin to be used in a photoresist composition.
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 disclosure of Masuyama by the simple substitution of a CF3 functional group in place of a methyl functional group onto the compound of formula (I) as the reference teaches that both substituents may be used in monomeric subunits to be polymerized into the resin for the taught photoresist composition.
Regarding Claim 5, Masuyama teaches the limitations of the claim as discussed above regarding claim 1.
Masuyama however does not teach an experimental embodiment meeting the limitations of claim 1 and thus does not teach an experimental embodiment meeting the limitations of claim 5. These limitations are met by the general disclosure of the reference.
The quencher of Masuyama is disclosed at [0198]-[0200] and exemplified by Quencher D1, a tris(t-butyl phenyl) sulfonium carboxylate salt at [0223].
Examples of the quencher include weak inner salts D at [0199] and the salts presented at [0198]:
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These salts meet the limitations of claimed formula (1) for where:
Rq1 is a C10-C12 hydrocarbyl group that contains a nitrogen
A+ is a sulfonium cation
Where the salts meet the limitations of claimed formula (2) for where:
Rq2 is a C1 or C10 hydrocarbyl group that may have an O atom therein
A+ is a sulfonium cation (onium cation)
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 incorporating the quenchers of Masuyama into the composition taught by the reference to arrive at a resist composition having improved CDU.
Regarding claims 11 and 12, Masuyama disclsoses a method for producing a pattern, wherein the resist composition is applied to a substrate, then dried to form a layer, then exposed to radiation/light. Exposure may be performed using ArF excimer lasers, KrF excimer lasers, and electron beam sources ([0204] – claim 12) After exposure, the composition layer is heated, then developed using a developer solution.
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 performing the taught method of Masuyama on the taught composition of the reference – such performance amounts to performing a known method (lithographic patterning) on a known product (a composition and a layer formed therefrom) with the expectation that it would result in the predictable result of a patterned photoresist layer.
Regarding Claims 7, 8, and 13, Masuyama teaches the limitations of the claims as discussed above regarding claim 1. However, as Masuyama does not teach a particular experimental embodiment meeting the totality of the claim limitations, it similarly does not teach the same for claims 7 and 13.
These limitations are met by the general disclosure of the reference.
The polymer of Masuyama comprises the subunits discussed above regarding claim 1 – a subunit conforming to formula (I) , a subunit comprising a phenolic subunit ((a2-A), and a subunit that meets the limitations of claimed formula C2 (II-2-A) as required by the claims.
The polymer of Masuyama further comprises at least one subunit (a1-0), (a1-1), and (a-2) as described from [0025]-[0036, (a1-5) as described from [0037]-[0040], (a2-1) as described form [0058]-[0062], and (a1-0X) as described from [0041]-[0047].
Exemplary monomer subunits include, but are not limited to those depicted at [0043]:
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These subunits meet the limitations of claims 7 and 13 where:
For formula (a1)
RA is a methyl group
ZC is a single bond
XA is an acid labile group free of a fluorinated aromatic ring (the tertiary carbon-containing groups bonded to the ester linkage).
Further subunits include those depicted at [0060]:
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These subunits meet the limitations of claims 8 and 13 for where:
For subunit (D1):
RA is H or methyl
ZE is a single bond or -CO-O-CH2-
ZE1 is a C1 saturated hydrocarbon
YA is a polar group containing two hydroxy moeities (the -OH-substituted adamantane – applicant’s own specification contemplates this group at page 89 in reference to units D at page 84).
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 incorporating these monomer subunits into the polymer of Masuyama and therefore incorporating the taught monomers into a polymer resin taught for photolithographic patterning with an expectation that their inclusion would result in a polymer resin similarly expected to be useful for lithographic patterning, - the incorporation of subunits having acid-labile groups as per the units discussed regarding claim 7 enable the switching of solubility of the resin upon action by an acid, and the incorporation of subunits having a hydroxy group as discussed regarding claim 8 improves the ([0047) improves the adhesion to the substrate by the resultant composition layer.
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.
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sally Merkling can be reached at 571-272-6297. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/A.P.T./Examiner, Art Unit 1737
/SALLY A MERKLING/SPE, Art Unit 1738
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