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 Amendment filed 06/25/2025 has been considered and is entered. Claims 1 and 7 have been amended. Claim 6 has been canceled. No new matter appears to have been entered with these amendments to the claims.
Response to Arguments
Applicant’s Amendments to the claims have rendered the scope of the claims outside that of the prior art used in the prior rejection. As such, all rejections have been withdrawn.
After further search and consideration, the Examiner makes a new grounds of rejection in view of Ohsawa et al (US 7235343 B2, published 06/26/2007) and Kinoshita (US 20180321585 A1) as laid out in the body of the rejection below.
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) 1-5 and 7-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ohsawa et al (US 7235343 B2, published 06/26/2007) and Kinoshita (US 20180321585 A1).
Regarding Claims 1-5, 14, and 16-19, Ohsawa discloses sulfonium photoacid generators and a chemically amplified resist composition comprising such, as well as a patterning process for the resist compositions described (Abstract).
The photoacid generator of Ohsawa is described from Column 6 Line 19 to Column 13 Line 13, and additional photoacid generators are described from Column 18 Line 20 to Column 21 Line 47.
Ohsawa describes a component (A), which is a resin that changes in solubility in alkali upon action by an acid. Ideal resins include polyhydroxystyrene and methacrylic acid ester resins, where further description of acid labile groups disposed upon the backbones of the resins are described from Column 13 Line 15 to Column 18 Line 13.
In the experimental examples, various polymer resins are detailed, of which two have been shown below:
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The polyhydroxystyrene unit meets the limitations of claim 1 for subunit (4) where:
R7 is hydrogen
R8 is a single bond
Subscript r is 0
Subscript s is 1
Ar2 is a phenyl ring
The ethylcyclopentyl methacrylate subunit meets the limitations of claim 1 for unit (1) where:
R1 is a methyl group
R2 is an ethyl group (monovalent C2 hydrocarbon)
R3 is a cyclopentyl ring with divalent substitution (1 for ethyl group, 1 for attachment to the carboxylate)
The subunit is present in 30 mol%, falling within the claimed range of 25-60 mol%
The polymer 21 is further used in the experimental examples 28-33 in Table 2.No nitrogen-containing heterocycles are recited therein.
Ohsawa does not teach a photosensitive acid generator conforming to the structure (2).
This limitation is met in analogous art by Kinoshita
Kinoshita discloses a radiation-sensitive composition including a first polymer having a structure that includes an acid-labile group, a radiation sensitive acid generator, and a compounds whose structure changes in response to action by an acid.
The acid generator (B) of the composition is as described from [0114]-[0181], wherein the acid generator is a sulfonium salt having a sulfonic acid, imide acid, amide acid, or methide acid counterion (this corresponds to the X- in Claimed Formula (2)).
The cation of the salt may be (Z-1), which has the generalized formula below:
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Where Ra1 and Ra2 each independently represent monovalent C1-C20 organic groups, Ra3 represents a C1-C20 monovalent organic group, hydroxy group, nitro group, or halogen atom. Integer k1 is a value of 0-5, and integer t1 is 0-3. As is further defined, the C1-C20 monovalent organic groups of Ra1 and Ra2 are preferably C6-C18 aromatic hydrocarbon groups that may be substituted (See [0153]), most preferably phenyl groups.
The general structure above reads upon the claimed structure (2) for where:
Ar1 is a naphthyl or anthracenyl group,
Subscript p is 1, q is 1 (Claim 2 and 4)
R5 is a hydroxy group, nitro group, halogen atom, or monovalent organic group with 1-20 carbons,
Each R4 is a C6-C18 aromatic hydrocarbon, preferably a phenyl ring
An exemplary anion provided is (4-1):
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Where Rp1 is a monovalent group having a ring of 5+ ring atoms; Rp2 is a divalent linking group; Rp3 and Rp4 each independently correspond to hydrogen, fluorine, or monovalent hydrocarbon or fluorinated hydrocarbon groups of 1-20 carbons; Rp5 and Rp6 each independently represent fluorine or monovalent fluorinated hydrocarbon groups of 1-20 carbons, (See [0123]).
The compositions of Ohsawa and Kinoshita are both used in patterning processes wherein the compositions are coated onto a substrate, baked, exposed through a mask to radiation, post exposure baked, and then developed Ohsawa – Column 6 Lines 5-12 and Column 30 Line 65 to Column 45 Line 35 , Kinoshita [0329]-[0344] – Claim 14)
Specific examples of the anion are provided in [0170], such as the ones below (Claims 3, 5, and 16-19) :
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In [0180], Kinoshita alleges that the inclusion of the above acid generator imparts improved LWR performance. As both Namai and Kinoshita are directed to compositions comprising acid generators, and sulfonium acid generators at that, the simple substitution of one acid generator for another in the name of improved properties is obvious.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by incorporating the acid generator of Kinoshita into the composition of Namai to arrive at a composition having improved LWR performance.
Regarding Claims 7-10 and 15, Ohsawa discloses sulfonium photoacid generators and a chemically amplified resist composition comprising such, as well as a patterning process for the resist compositions described (Abstract).
The photoacid generator of Ohsawa is described from Column 6 Line 19 to Column 13 Line 13, and additional photoacid generators are described from Column 18 Line 20 to Column 21 Line 47.
Ohsawa describes a component (A), which is a resin that changes in solubility in alkali upon action by an acid. Ideal resins include polyhydroxystyrene and methacrylic acid ester resins, where further description of acid labile groups disposed upon the backbones of the resins are described from Column 13 Line 15 to Column 18 Line 13.
In the experimental examples, various polymer resins are detailed, of which two have been shown below:
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The polyhydroxystyrene unit meets the limitations of claim 1 for subunit (5) where:
R10 is hydrogen
Subscript t is 0
Subscript u is 1
Ar3 is a phenyl ring
The hydroxystyrene is present in 70mol%, falling outside the claimed range, however in view of other embodiments (Polymers 25-28, for instance) , hydroxystyrene is taught in a range of 65 to 85 mol%. A person of ordinary skill in the art would find it obvious to experiment with the range of monomer incorporation so as to tune the properties of the resist composition to perform optimally upon development with an alkaline developer (such , and as such would find it obvious to arrive at embodiments that are close (60%, possibly 55% ) to the prior art range where such optimization overlaps with the claimed range.
The ethylcyclopentyl methacrylate subunit meets the limitations of claim 1 for unit (6) where:
R12 is a methyl group
R13 is an ethyl group (monovalent C2 hydrocarbon)
R14 is a cyclopentyl ring with divalent substitution (1 for ethyl group, 1 for attachment to the carboxylate)
The polymer 21 is further used in the experimental examples 28-33 in Table 2.No nitrogen-containing heterocycles are recited therein.
Ohsawa does not teach a photosensitive acid generator conforming to the structure (2).
This limitation is met in analogous art by Kinoshita.
Kinoshita discloses a radiation-sensitive composition including a first polymer having a structure that includes an acid-labile group, a radiation sensitive acid generator, and a compounds whose structure changes in response to action by an acid.
The acid generator (B) of the composition is as described from [0114]-[0181], wherein the acid generator is a sulfonium salt having a sulfonic acid, imide acid, amide acid, or methide acid counterion (this corresponds to the X- in Claimed Formula (2)).
The cation of the salt may be (Z-1), which has the generalized formula below:
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Where Ra1 and Ra2 each independently represent monovalent C1-C20 organic groups, Ra3 represents a C1-C20 monovalent organic group, hydroxy group, nitro group, or halogen atom. Integer k1 is a value of 0-5, and integer t1 is 0-3. As is further defined, the C1-C20 monovalent organic groups of Ra1 and Ra2 are preferably C6-C18 aromatic hydrocarbon groups that may be substituted (See [0153]), most preferably phenyl groups.
The general structure above reads upon the claimed structure (2) for where:
Ar1 is a naphthyl or anthracenyl group,
Subscript p is 1, q is 1 (claim 8)
R5 is a hydroxy group, nitro group, halogen atom, or monovalent organic group with 1-20 carbons (Claim 10)
Each R4 is a C6-C18 aromatic hydrocarbon, preferably a phenyl ring
An exemplary anion provided is (4-1):
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Where Rp1 is a monovalent group having a ring of 5+ ring atoms; Rp2 is a divalent linking group; Rp3 and Rp4 each independently correspond to hydrogen, fluorine, or monovalent hydrocarbon or fluorinated hydrocarbon groups of 1-20 carbons; Rp5 and Rp6 each independently represent fluorine or monovalent fluorinated hydrocarbon groups of 1-20 carbons, (See [0123]) (claim 9).
The compositions of Ohsawa and Kinoshita are both used in patterning processes wherein the compositions are coated onto a substrate, baked, exposed through a mask to radiation, post exposure baked, and then developed (Ohsawa – Column 6 Lines 5-12 and Column 30 Line 65 to Column 45 Line 35 , Kinoshita [0329]-[0344] – Claim 15)
Specific examples of the anion are provided in [0170], such as the ones below :
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In [0180], alleges that the inclusion of the above acid generator imparts improved LWR performance. As both Ohsawa and Kinoshita are directed to compositions comprising acid generators, and sulfonium acid generators at that, the simple substitution of one acid generator for another in the name of improved properties is obvious.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by incorporating the acid generator of Kinoshita into the composition of Ohsawa to arrive at a composition having improved LWR performance.
Regarding claim 12 and 13, the compositions of Ohsawa are as described above regarding claims 1 and 7 respectively – Ohsawa makes mention of exposure to EB radiation exposure in the context of the polymer and resist described in the rejections above (column 6 line 5-12). A person of ordinary skill in the art would have found it obvious to use EB radiation for exposure from the general disclosure of the reference, as it ascribes to the composition improved sensitivity to these radiation sources.
Further – the recitation of these two claims is being treated as intended use, as there is no positive limitation describing the practice of use of the EUV or EB exposure, only that the composition(s) be “suitable”. As claims 1 and 7 have been met, and the limitations of these claims are carried down by nature of dependency, all positive limitations are by default met for these two claims.
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
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734