DETAILED ACTION
Claims 10-13, 15, 16, 18-23, and 25-30 are pending. Claims 10, 29, and 30 have been amended and claims 1-9, 14, 17, and 24 were previously canceled.
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 .
Specification
[AltContent: oval][AltContent: oval][AltContent: oval]The disclosure is objected to because of the following informalities: Pages 44-46 show resins produced in the Examples and Comparative Examples. However, the formulas are incorrect as they depict all of the structural units having a hydrogen atom as the backbone, e.g. Example 1 has the following formula:
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while the description of the resins on pages 34-43 indicate that each monomer used is a methacrylate and not an acrylate. Therefore, each formula shown must have a methyl group attached to the backbone of the resultant resins.
Appropriate correction is required.
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.
Claims 10-13, 15, 16, 18-23, and 25-29 are rejected under 35 U.S.C. 103 as being unpatentable over Kaneko et al. (U.S. 2010/0104974) in view of Hirano et al. (U.S. 2015/0185610).
Kaneko et al. teaches a positive resist composition comprising: (A) a compound that generates an acid upon irradiation with an actinic ray or radiation (acid generator); and (B) a resin that has an acid-decomposable repeating unit represented by formula (I'), has a dispersity of 1.5 or less and increases its solubility in an alkali developer by action of an acid [0010-0012] (claims 10, 27, 29, and 30) wherein the resin (B) is a resin produced by living radical polymerization. The positive resist composition, wherein the resin (B) is a resin polymerized in the presence of a chain transfer agent represented by formula (CT) [0016-0017] wherein a specific example includes the following formula (II-11):
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[0225] which is equivalent to a chain transfer agent containing no cyano group and containing a thiocarbonylthio group, specifically a didithiobenzoate providing as a substituent on the resin end, a group having an ester bond of instant claims 10-13, 22, 29, and 30. Kaneko et al. also teaches an example of the synthesis method includes the synthesis of Resin (RA-1-1): Under a nitrogen stream, 0.77 g (2.50 mmol) of Chain Transfer Agent (II-1) and 5.9 g of cyclohexanone were charged into a three-neck flask and heated at 80°C. Thereto, a solution prepared by dissolving 10.9 g (64.0 mmol) of Monomer (I-1), 6.0 g (25.6 mmol) of Monomer (I-2), 11.2 g (38.4 mmol) of Monomer (I-3) and 0.41 g (2.50 mmol) of polymerization initiator V-60 (azobisisobutyronitrile, produced by Wako Pure Chemical Industries, Ltd.) in 106 g of cyclohexanone was added dropwise over 6 hours. After the completion of dropwise addition, the reaction was further allowed to proceed at 80°C for 2 hours. To this solution, a solution prepared by dissolving 3.36 g (10.2 mmol) of polymerization initiator V-60 (produced by Wako Pure Chemical Industries, Ltd.) in 20 mL of cyclohexanone was added dropwise at 80°C over 4 hours, and the system was further heated for 2 hours. The reaction solution was left standing to cool and then added dropwise to a mixed solution of 700-ml hexane/300-ml ethyl acetate over 20 minutes, and the precipitated powder was collected by filtration and dried to obtain 21.4 g of Acid-Decomposable Resin (RA-1-1) [0342] and other examples of the polymerization initiator include dimethyl 2,2'-azobis(2-methylpropionate) [0228] such that when Chain Transfer Agent (II-1) is replace by formula (II-11) and polymerization initiator V-60 is replaced by dimethyl 2,2'-azobis(2-methylpropionate) in both occurrences, it is equivalent to a resin having no cyano group at a resin end obtained by polymerizing monomers in the presence of a chain transfer agent having no cyano group, an azo compound polymerization initiator containing no cyano group, and an end treatment agent azo compound containing no cyano group of instant claims 11-13, 15, 16, 22, 23, 25, and 26. Kaneko et al. does not teach a polymerization unit represented by Formula (a3) or Formula (a1).
However, Hirano et al. teaches an actinic ray-sensitive or radiation-sensitive resin composition containing (Ab) a resin having a repeating unit represented by the following formula (Ab1) and a repeating unit represented by formula (A) [0212]:
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[0212] wherein R' represents a hydrogen atom or an alkyl group. L1 represents a hydrogen atom or an alkyl group. L1 may combine with L to form a ring and in this case, L1 represents an alkylene group or a carbonyl group. L represents a single bond or a divalent linking group, and when L1 and L combine to form a ring, L represents a trivalent linking group. R1 represents a hydrogen atom or a monovalent substituent. R2 represents a monovalent substituent, and R1 and R2 may combine with each other to form a ring. R3 represents a hydrogen atom, an alkyl group or a cycloalkyl group [0213-0218], R' is preferably a hydrogen atom or an alkyl group having a carbon number of 1 to 5, more preferably a hydrogen atom or an alkyl group having a carbon number of 1 to 3, still more preferably a hydrogen atom, a methyl group or an ethyl group [0234], L is preferably a single bond [0244], the monovalent substituent of R1 is preferably a group represented by C(R111)(R112)(R1113). * indicates a bond connected to a carbon atom in the repeating unit represented by formula (Ab1). Each of R111 to R113 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a heterocyclic group [0246], specific examples of the group represented by R2 include a methyl group [0273], and a specific example of R2 includes the following:
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[0315] such that when R’ is an ethyl group, L is a single bond, R1 and R3 are methyl groups, and R2 is (un)substituted cyclohexane it is equivalent to a polymerization unit represented by Formula (a3) of instant claims 29 and 30 when R is an alkyl group having 2 carbon atoms, A is a single bond, R5 and R6 are alkyl groups having 1 carbon atom, Z1 is a cyclohexane ring, and p is 0 or 2 when Ra is an alkyl group having 1 or 3 carbon atoms. Hirano et al. also teaches a specific example of formula (Ab1) is illustrated below, but the present invention is not limited thereto [0317]:
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[0317] which is equivalent to a polymerization unit represented by Formula (a3) of instant claim 10 when R is an alkyl group having 1 carbon atom, A is a single bond, R2 and R3 are alkyl groups having 1 carbon atom, Z1 is a cyclohexane ring, and p is 0. Hirano et al. further teaches it is considered that the resin (Ab) having a repeating unit represented by formula (Ab1) is increased in its the reactivity with an acid and at the same time, the polarity change associated with decomposition of the resin by an acid becomes large. This large change in polarity is considered to produce an effect that the dissolution contrast for an organic solvent-containing developer between the exposed area and the unexposed area as well as the sensitivity and resolution at the formation of an isolated line pattern and an isolated space pattern are enhanced and the pattern profile is improved [0076-0077].
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the teachings of Kaneko et al. to include the repeating unit of Hirano et al. and arrive at the instant claims through routine experimentation of combining equally suitable components for the sought invention in order to achieve optimum sensitivity and resolution.
With regard to claims 18 and 19, Kaneko et al. teaches the resin as the component (B) preferably further contains a repeating unit having at least one kind of a group selected from a lactone group, a hydroxyl group, cyano group and an alkali-soluble group [0170] and a specific example of the repeating unit having a lactone structure includes the following [0181]:
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[0181] wherein Rx is H, CH3, CH2OH or CF3 [0181] which is equivalent to a polymerization unit represented by formula (b4) of instant claim 18 when R is a hydrogen atom, an alkyl group having 1 carbon atom, or an alkyl group having 1 carbon atom having halogen atoms, A is a single bond, Z is a divalent organic group, and R10 is a hydrogen atom; and specific examples of the repeating unit having a hydroxyl group includes the following [0190]:
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[0190] which is equivalent to a polymerization unit represented by formula (c1) of instant claim 19 when R is a hydrogen atom, A is a single bond, Z2 is an alicyclic hydrocarbon group having 10 carbon atoms, and q is 1 where Rb is a hydroxy group.
With regard to claims 20 and 21, Kaneko et al. teaches the weight average molecular weight of the resin (B) for use in the present invention is preferably from 1,000 to 200,000, more preferably from 3,000 to 20,000, and most preferably from 5,000 to 15,000, in terms of polystyrene by the GPC method. When the weight average molecular weight is from 1,000 to 200,000, the heat resistance, dry etching resistance and developability can be prevented from deterioration and also, deterioration in the film-forming property due to high viscosity can be prevented [0232] and the dispersity of the polymer for use in the present invention is 1.5 or less, preferably from 1.0 to less than 1.40, more preferably from 1.0 to less than 1.30. As the molecular weight distribution is smaller, the side wall of the resist pattern is smoother, and the property in terms of roughness is more improved [0233].
With regard to claim 28, Kaneko et al. teaches the positive resist composition is coated on such a substrate (e.g., silicon/silicon dioxide-coated substrate) as used in the production of a precision integrated circuit device, by an appropriate coating method such as spinner or coater, and dried to form a resist film. The resist film formed is irradiated with an actinic ray or radiation through a predetermined mask and preferably after baking (heating), subjected to development and rinsing, whereby a good pattern can be obtained [0324-0325] where in the development step, an alkali developer is used [0330].
Response to Arguments
Due to the amendment filed June 18, 2026 of instant claims 10, 29, and 30, the 103 rejection over Kaneko and Kaneko in view of Funaki have been withdrawn. Applicants’ arguments with regard to these rejections have been considered but are moot due to the amendment of instant claims 10, 29, and 30. However, Kaneko is still being used as prior art because it continues to teach the claimed polymerization method resulting in a resin having no cyano group at a resin end.
Applicants’ arguments with regard to the objection to the specification have been fully considered but are not persuasive. Applicant argues the description of the resins in the Examples are correct. Specifically, the descriptions of the examples on pages 33-43 of the present specification refer to monomers. On the other hand, the formulas on pages 44-46 show polymerization units. The polymerization unit is a repeating unit within a larger molecule, and a monomer is a molecule that exists independently prior to polymerization.
The Examiner agrees that the compounds recited on pages 33-43 are the monomers and the formulas on pages 44-46 are polymerization units. The objection is based on the absence of a methyl group on each polymerization unit shown on pages 44-46. Specifically, Example 1 (and Comparative Example 1) is made from monomers 6-cyano-5-oxo-4-oxatricyclo[4.2.1.03,7]nonan-2-yl methacrylate, 5,5,-dioxo-4-oxa-5-thiatricyclo[4.2.1.03,7]nonan-2-yl methacrylate, and 1-(adamantan-1-yl)-1-methylpropyl methacrylate. However, the Formula shown on page 44 can only be produced if acrylate monomers were used, not methacrylate monomers. Thus, the formula requires a methyl group on the backbone of each polymerization unit. The same issue is true for all of the examples.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. U.S. 2016/0048082 and U.S. 2008/0248419.
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 ANNA E MALLOY whose telephone number is (571)270-5849. The examiner can normally be reached 6:30-3:00 EST M-F.
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/Anna Malloy/ Examiner, Art Unit 1737
/KEITH WALKER/ Supervisory Patent Examiner, Art Unit 1735
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