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 .
Response to Amendment
Applicant’s Amendments filed 12/19/2025 have been entered and are being considered. Claim 1 has been amended. Claims 4, 7, and 11 have been amended to improve form. No new matter has been added with these amendments.
Response to Arguments
Applicant’s Amendments regarding claims 4, 7, and 11 have rendered the 35 USC 112(b) rejections thereover moot. The rejections of these claims is withdrawn.
Regarding the Amendment and arguments based thereon, the Examiner does acknowledge that the amendments change the scope of the independent claim 1 – but does not amend the scope to completely avoid the scope of the prior art. The amendment made seems to be focused on the acetal linker/component of the anions of Nishimura:
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Where the acetal is the -O-CH(CH3)-O- group in the anions
These anions are exemplary embodiments of the anion but are not the sum total of the disclosure and were not the sum total of the reasons for the rejection over 35 USC 103 in combination with Komuro. Exemplary embodiments are not the sole teaching of a reference – and exemplary embodiments do not negate or render unimportant alternative embodiments suggested by a reference (See MPEP 2123). The prior rejection was made in view of the generalized formula of the salt and anion of Nishimura and not solely the depicted examples, replicated here from the body of the rejection below:
Nishimura discloses a salt represented by formula (I) (discussed from [006]-[0015] and [0054]-[0085]:
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Where:
Q1 and Q2 may each independently be a F atom or a C1-C6 perfluoroalkyl group
R1 and R2 in occurrence each independently represent a F, H, or C1-C6 perfluoroalkyl group
Subscript z is 1-6
X1 is a -CO-O- group, -O-CO-, or -O- group, where the group is bound to C(R1)(R2) or C(Q1)((Q2),
A1 is a C4-C24 hydrocarbon group having a C4-C18 divalent alicyclic moeity
A2 is a C2-C12 divalent hydrocarbon
R3 and R4 each independently represent a H or a C1-C6 saturated hydrocarbon group
R5 is an H, F, or C1-C6 alkyl group that may be optionally fluorosubstituted
Z+ is an organic cation, which may be a sulfonium cation or iodonium cation ([0086])
As bolded above – R3 and R4 are not restricted to the embodiments where one of R3/R4 is an H and the other of R3/R4 is CH3 by the disclosure of the reference. R3 and R4 may be, for instance- each be H, or the moeity may be a Ketal where both R3 and R4 are C1-C6 alkyl groups, or the acetal moeity may be one where R3/R4 is H and the other of R3/R4 is a C2-C6 hydrocarbon. If applicant wishes to amend to negate this entire group’s scope, they may do so at their discretion but the Examiner will point out that such amendments must have support in the specification to avoid issues of new matter.
Regarding the obviousness and motivation to include the anion of Nishimura into the composition of Komuro - Nishimura teaches that the salt can be used for a resin in a resist composition that is capable of providing a resist film with reduced line edge roughness and thus useful in fine processing for semiconductors ([0766]). A person of ordinary skill in the art would have found it obvious to incorporate the anion and anion-salt resin of Nishimura to the composition of Komuro to arrive at a salt and composition that improves the line edge roughness of a resultant patterned resist. The motivation for inclusion is one of improved performance.
Evidence regarding unexpected and superior results would be sufficient to overcome the obviousness rejection made herein, so long as such evidence is statistically and practically significant and commensurate with the scope of the claims.
The 35 USC 103 rejection of claims 1-22 is maintained. The body of the rejection has been edited slightly to reflect the amendment to the claims regarding methyl acetal -O-CH(CH3)-O- , but the thrust of the rejection over the disclosed salt anion of Nishimura remains the same.
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) 1-22 is/are rejected under 35 U.S.C. 103 as being unpatentable over Komuro et al (US 20210341836 A1, published 11/04/2021) and Nishimura et al (US 20180113382 A1).
Regarding Claims 1-17, Komuro et al teaches a salt represented by a chemical formula, an acid generator, and a resist composition (Abstract).
The specific salt of Komuro conforms to the formula (1) as described from [0050]-[0267], where the salt is an acid generator, delimited more specifically at [008]-[0028].
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R1-R3 reach represent a hydroxyl group, -O-R10, -O-CO-O-R10, or -O-L1-CO-O-R10 (claim 5)
L1 represents a C1-C6 alkanediyl group
R4-R9 each independently may be a halogen, C1-C6 alkyl fluoride, or C1-C18 hydrocarbon group, where the C1-C18 hydrocarbon group may be substituted and a methylene linkage therein may be replaced with oxy, sulfo, carbonyl, or sulfonyl groups
R10 is an acid labile group
X1-X3 may each be an O or S atom
Subscript m1 is 1-5
Subscript m2 and m3 are 0-5, subscripts m4-m7 are 0-4, subscripts m8-m9 are 0-5
A1- is an organic anion
The above formula reads upon the generally claimed cation of claim 1 for where:
R1-R3 reach represent a hydroxyl group, -O-R10, -O-CO-O-R10, or -O-L1-CO-O-R10
L1 represents a C1-C6 alkanediyl group
R4-R9 each independently may be a halogen, C1-C6 alkyl fluoride, or C1-C18 hydrocarbon group, where the C1-C18 hydrocarbon group may be substituted and a methylene linkage therein may be replaced with oxy, sulfo, carbonyl, or sulfonyl groups
R10 is an acid labile group
A1-A3 may each be an O or S atom
a C1 alkanediyl group that is replaced with -O-, or -S-, meets the limitations of the claim - see reference’s X1-X3
For claims 2-4, A1-A3 may each be X01-L01 or L01-X01 (or a corresponding 02 or 03- variant) where X01-X03 are each -O- or -S- and L01-L03 are each a single bond.
Subscript m1 is 1-5
Subscript m2 and m3 are 0-5, subscripts m4-m7 are 0-4, subscripts m8-m9 are 0-5
Specific examples of the cation are depicted at [0118], some of which are replicated here:
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The above cations have acid labile groups that correspond to acid-cleavable sites at both the ester group and at the phenolic oxygen, meeting the limitations of claim 1 where R1 is -O-L1-CO-O-R10, where L1 is a methylene linkage, and where R10 meets the limitations of claim 6 for where:
Regarding formula (1a)
R10 is a t-butyl group, where Raa1-Raa1- are each C1 alkyl
R10 is a methyl adamantyl group, where Raa3 is a methyl group and Raa2 and Raa1 are an alicyclic group having 10 carbon atoms
Regarding formula (2a)
R10 is a group where Raa1’ is a hydrogen, and Raa2’ and Raa3’ are bonded together to form a heterocyclic group having 6 members where Xa is an O atom
R10 is a group where Raa1’ is a hydrogen, Raa2 is a methyl group, and Raa3’ is an ethyl group, where Xa is an O atom
Two or more acid generators, including the salt of formula (1), may be used in the composition ([0269] – a second acid generator may be referred to as generator (B), and may be an acid generator as described from [0268]-[0322]
The resist composition of Komuro comprises an acid generator including the salt of formula (1) and a resin having an acid-labile group, as well as other components such as quenchers and solvents ([0324]).
Komura does not teach an anion that meets the claim limitations of the anion delimited by the anion in formula (I). Komuro does teach a resin having an acid monomer derived from a sulfonate anion, but such anion does not meet the claim limitations ([0652]-[0688]).
This limitation is met by Nishimura.
Nishimura discloses a salt represented by formula (I) (discussed from [006]-[0015] and [0054]-[0085]:
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Where:
Q1 and Q2 may each independently be a F atom or a C1-C6 perfluoroalkyl group
R1 and R2 in occurrence each independently represent a F, H, or C1-C6 perfluoroalkyl group
Subscript z is 1-6
X1 is a -CO-O- group, -O-CO-, or -O- group, where the group is bound to C(R1)(R2) or C(Q1)((Q2),
A1 is a C4-C24 hydrocarbon group having a C4-C18 divalent alicyclic moeity
A2 is a C2-C12 divalent hydrocarbon
R3 and R4 each independently represent a H or a C1-C6 saturated hydrocarbon group
R5 is an H, F, or C1-C6 alkyl group that may be optionally fluorosubstituted
Z+ is an organic cation, which may be a sulfonium cation or iodonium cation ([0086])
Example anions are presented in [0085].
The disclosed anion(s) of Nishimura meet the limitations of the claim for where:
Rbb1 is H, F, or C1-C6 alkyl group that may be optionally fluorosubstituted (reference’s R5)
X10 is a single bond (claims 9 and 10)
L10 is a C4-C36 hydrocarbon group where two and more hydrocarbons are substituted by -O- (reference’s -C(R3)(R4)--O-A2-O-*, where * is the bonding site to the carbonyl), where R3 and R4 are together not H and CH3.
Yb1 is an alicyclic hydrocarbon having 4-24 hydrocarbons where one C1-linkages is substituted by -O- (reference’s -A1-O-) (claim 7)
In the examples, Yb1 may comprise an adamantanediyl group (claim 8)
Lb1 is a C1-C24 hydrocarbon group, where one C1-linkage may be substituted with -O-, two continuous C1-linkages may be substituted with -CO- and -O- in either order, and where hydrogens may be substituted with F atoms (reference’s (-(C(R1)(R2))z-X1-)
In the above examples, Lb1 corresponds to a C1 or C2 hydrocarbon that where the methylene linkages are substituted with -O- and/or -CO, as well as C3 hydrocarbon where one or two methylene linkages are substituted with -O- and/or -CO- (claim 11)
Q1 and Q2 are each independently an F atom or a C1-C6 perfluoroalkyl group
The resin of Nishimura comprises the salt having the anion above and a corresponding cation counterion as part of a composition as a structural unit of an acid generating resin ([0149]-[0152] (claim 12-14), where the resin further has a structural unit having an acid labile group (claim 15-17). The composition also comprises the salt as part of the composition, and may be present in combination with another known acid generator ([0147]-[0148]).
Nishimura teaches that the salt can be used for a resin in a resist composition that is capable of providing a resist film with reduced line edge roughness and thus useful in fine processing for semiconductors ([0766]). A person of ordinary skill in the art would have found it obvious to incorporate the anion and anion-salt resin to the composition of Komuro to arrive at a cation-anion resin and improving the line edge roughness of a resultant patterned resist.
Regarding claims 18 and 19, Komuro and Nishimura disclose the limitations of the claims as discussed above regarding claims 1, 14, and 15.
Komuro and Nishimura however do not disclose experimental embodiments that meet the limitations of the claims 18 and 19 having structural units corresponding to acrylate/methacrylate esters and styrene derivatives.
These limitations are met by Komura’s general disclosure.
Komuro teaches the base resin composition from [0326]-[0708], where the resin comprises an acid labile group-bearing substituent such as those bounded by formulas (a1-0) to (a1-2) in [0356]-[0384]:
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Where, as is also present in the claimed invention’s claim 18 :
La01, La1, and La2 reach represent oxo a linkage defined in [0358]
Ra01, Ra4, and Ra5 represent H, halogen, or a C10C6 alkyl group that may be halogenated
Ra02, Ra03 and Ra40 each independently represent an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group obtained by combining these groups
Ra6 and Ra7 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these groups,
Subscript m1' represents an integer of 0 to 14, n1 represents an integer of 0 to 10, and n1' represents an integer of 0 to 3.
Examples of the subunit are disclosed in [0381].
The resin of Komuro also discloses a second subunit may be present, unit (a2-A), described as in [0444]-[0469] including examples:
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Ra50 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom,
Ras51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group,
Aa50 represents a single bond or *-Xa51-(Aa52-Xa52)nb- and * represents a bonding site to carbon atoms to which - Ra50 is bonded,
Aa52 represents an alkanediyl group having 1 to 8 carbon atoms,
Xa51 and Xa52 each independently represent -0-, -CO-0- or -O-CO-,
subscript nb represents 0 or 1,
subscript mb represents an integer of 0 to 4, and when mb is an integer of 2 or more, a plurality of Ra5 may be the same or different from each other
These limitations are verbatim with claimed formula (a2-A) in claim 19.
Komuro ascribes improved resolution to resists when the structural units (a1-0)-(a1-2) are present ( [0355]) and improved resolution when using structural units (a2) such as unit (a2-A) ([0441]). A person of ordinary skill in the art would have found it obvious to incorporate the units of Komuro into a resist resin such as that of Komuro and Nishimura in order to improve the resolution of a resultant resist pattern formed from processing.
Regarding claim 20, Komuro and Nishimura teach the limitations of the claim as set forth above regarding claims 1 and 14.
Komuro and Nishimura however do not disclose experimental examples that read upon the claims 1, 14, and 20 for the salt (B1).
This limitation is met by the general disclosure of Komuro, which discloses a salt acid generator (B1) from [0268]-[0322]:
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Qbl and Qb2 each independently represent a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms,
Lb1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, -CH2- included in the divalent saturated hydrocarbon group may be replaced by -0- or -CO-, and a hydrogen atom included in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group,
Y represents a methyl group which may have a substituent, or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH2- included in the alicyclic hydrocarbon group may be replaced by -0-, - S-, -SO2- or -CO-,
Z1+ represents an organic cation
The above limitations read nearly verbatim with claim 20 except where Z+ is Z1+. Further examples of salt compounds corresponding to (B1) are depicted from [0316]-[0321].
Komuro discloses that B1 and the salt (1) (and more, additional acid generators) may be used in combination. A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by incorporating the acid generator salt (B1) into the resist composition of Komuro and Nishimura to improve the resist composition’s sensitivity.
Regarding claim 21, Komuro and Nishimura teach the limitations of the claim as discussed above regarding claims 1 and 14.
Komuro and Nishimura however do not explicitly teach experimental embodiments meeting the limitations of the claim for a salt generating an acid having an acidity lower than that of an acid generated from the salt (1).
The composition of Komuro teaches a quencher from [0720]-[0726], where the composition’s quencher may be a salt generating an acid having acidity lower than that of an acid generated from the acid generators (B), such as a carboxylic acid such as adamantyl carboxylic acid or acetic acid (see Page 112).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of Komuro, incorporating the quencher of Komuro into the composition of Komuro and Nishimura to improve the resolution of a resultant resist pattern formed from the composition.
Regarding claim 22, Komuro and Nishimura teach the limitations of the claim as discussed above regarding claims 1 and 14.
Komuro and Nishimura however do not explicitly teach experimental embodiments meeting the limitations of the claim for a lithographic process using the compositions of claims 1 and 14.
These limitations are met by Komuro, which discloses a lithographic process involving the production of a resist pattern, where the resist composition is applied to a substrate, dried to form a film or composition layer, then exposed to radiation, then heated after exposure, and then developed to produce the pattern ([0730]-[0745]).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of Komuro, using the composition of Komuro and Nishimura to arrive at a patterned resist product having high resolution imparted by the composition used to make it.
Conclusion
THIS ACTION IS MADE FINAL. 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
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734