DETAILED ACTION
Claims 10-13, 15, 16, 18-23 and 25-30 are pending. Claim 10 has been amended, claims 1-9, 14, 17, and 24 were previously canceled, and claims 29 and 30 have been added.
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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on February 13, 2026 has been entered.
Specification
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 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.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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).
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] (claim 27) 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 of instant claims 10, 12, and 22. Kaneko et al. also teaches the polymerization method includes a method of performing the polymerization by heating a solution containing monomers, a polymerization initiator and a chain transfer agent of formula (CT) (batch polymerization), and a method of performing the polymerization while adding a solution containing monomers to a heated solution (dropping polymerization), but a dropping polymerization method is preferred in view of production stability. The monomers, polymerization initiator and chain transfer agent may be separately added to the reaction system or may be added as a mixture. In the case of separately adding these to the reaction system, the addition time may be the same or different, and the addition initiating time may be staggered. In the present invention, the reaction system may be a reaction solvent itself or may be a reaction solvent where some selected from monomers, a polymerization initiator and a chain transfer agent are previously added. More specifically, in the present invention, monomers may be polymerized using a reaction solvent itself as the reaction system while adding monomers, a polymerization initiator and a chain transfer agent thereto, or after preparing a reaction system by previously adding some selected from monomers, a polymerization initiator and a chain transfer agent to a reaction solvent, monomers may be polymerized while adding the remaining monomers, polymerization initiator and chain transfer agent thereto. In particular, it is preferred to prepare a reaction system by adding the entire amount of a chain transfer agent used and depending on the case, adding some of monomers and a polymerization initiator and then add the remaining monomers and polymerization initiator thereto [0227]. Kaneko et al. further teaches as for the polymerization initiator, a commercially available radical initiator (e.g., azo-based initiator, peroxide) can be used. The radical initiator is preferably an azo-based initiator, and an azo-based initiator having an ester group, a cyano group or a carboxyl group is preferred. Preferred examples of the initiator include dimethyl 2,2'-azobis(2-methylpropionate) [0228] which is equivalent to an azo compound polymerization initiator containing no cyano group of instant claims 12, 15, 22, and 25 as well as an end treatment agent azo compound containing no cyano group of instant claims 13, 16, 23, and 26. Kaneko et al. also teaches a specific example of the resin (B) includes the following resin (RA-5) from Synthesis Example 6:
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[page 43] which has a weight average molecular weight of 5500 and dispersity (Mw/Mn) of 1.17 (claims 10, 20, and 21) wherein the bottom repeating unit is equivalent to a polymerization unit represented by formula (a4) of instant claim 10 when R is an alkyl group having 1 carbon atom, A is a single bond, Z1 is a cycloalkane ring, p is 0, and n is 1 where R7 is -COORc where Rc is a tertiary hydrocarbon group; the top left repeating unit is equivalent to a polymerization unit represented by formula (b3) of instant claim 18 when R is an alkyl group having 1 carbon atom, A is a single bond, X is a methylene group, Y is a methylene group, and R10 is a hydrogen atom; and the top right repeating unit is equivalent to a polymerization unit represented by formula (c1) of instant claim 19 when R is an alkyl group having 1 carbon atom, A is a single bond, Z2 is an alicyclic hydrocarbon group having 7 carbon atoms, and q is 1 where Rb is a cyano group. Kaneko et al. further teaches an object of the present invention is to provide a positive photosensitive composition ensuring that even in the formation of a fine pattern, the pattern collapse and line edge roughness performance are improved and a pattern with good profile is formed, and a pattern forming method using the composition [0007] and the present invention is described in greater detail [below] by referring to Examples, but the present invention should not be construed as being limited thereto [0340].
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 specific teachings of Kaneko et al. to obtain resin (RA-5) by a living radical polymerization method including the above specified chain transfer agent and initiator and arrive at the instant claims through routine experimentation of substituting equally suitable compounds for the sought invention in order to improve pattern collapse and line edge roughness. The resin of Kaneko et al. performed using the above method and the above specified chain transfer agent and initiator is expected to result in a resin containing no cyano group at a resin end and having at its end a substituent which is a group having an ester bond of instant claims 10-13, 15, 16, 22, 23, 25, and 26, absent any evidence to the contrary.
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].
With regard to claim 29, 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] 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 of instant claim 29. Kaneko et al. also teaches the polymerization method includes a method of performing the polymerization by heating a solution containing monomers, a polymerization initiator and a chain transfer agent of formula (CT) (batch polymerization), and a method of performing the polymerization while adding a solution containing monomers to a heated solution (dropping polymerization), but a dropping polymerization method is preferred in view of production stability. The monomers, polymerization initiator and chain transfer agent may be separately added to the reaction system or may be added as a mixture. In the case of separately adding these to the reaction system, the addition time may be the same or different, and the addition initiating time may be staggered. In the present invention, the reaction system may be a reaction solvent itself or may be a reaction solvent where some selected from monomers, a polymerization initiator and a chain transfer agent are previously added. More specifically, in the present invention, monomers may be polymerized using a reaction solvent itself as the reaction system while adding monomers, a polymerization initiator and a chain transfer agent thereto, or after preparing a reaction system by previously adding some selected from monomers, a polymerization initiator and a chain transfer agent to a reaction solvent, monomers may be polymerized while adding the remaining monomers, polymerization initiator and chain transfer agent thereto. In particular, it is preferred to prepare a reaction system by adding the entire amount of a chain transfer agent used and depending on the case, adding some of monomers and a polymerization initiator and then add the remaining monomers and polymerization initiator thereto [0227]. Kaneko et al. further teaches as for the polymerization initiator, a commercially available radical initiator (e.g., azo-based initiator, peroxide) can be used. The radical initiator is preferably an azo-based initiator, and an azo-based initiator having an ester group, a cyano group or a carboxyl group is preferred. Preferred examples of the initiator include dimethyl 2,2'-azobis(2-methylpropionate) [0228]. Kaneko et al. also teaches a specific example of the resin (B) includes the following resin (RA-5) from Synthesis Example 6:
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[page 43] which has a dispersity (Mw/Mn) of 1.17 (claim 29) wherein the bottom repeating unit is a specific example of formula (I’), specifically the following [0111]:
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[0111] wherein Xa1 is the same meaning as Xa1 in formula (I’) [0111] which is a hydrogen atom, an alkyl group, a cyano group or a halogen atom [0099] such that when Xa1 is a halogen atom or alkyl group having more than 1 carbon atom for the above repeating unit it is equivalent to a polymerization unit represented by formula (a4) of instant claim 29 when R is an alkyl group having 1 carbon atom, A is a single bond, Z1 is a cycloalkane ring, p is 0, and n is 1 where R7 is -COORc where Rc is a tertiary hydrocarbon group. Kaneko et al. further teaches an object of the present invention is to provide a positive photosensitive composition ensuring that even in the formation of a fine pattern, the pattern collapse and line edge roughness performance are improved and a pattern with good profile is formed, and a pattern forming method using the composition [0007] and the present invention is described in greater detail [below] by referring to Examples, but the present invention should not be construed as being limited thereto [0340].
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 specific teachings of Kaneko et al. to obtain a resin having the above defined repeating unit obtained by a living radical polymerization method including the above specified chain transfer agent and initiator and arrive at the instant claims through routine experimentation of substituting equally suitable compounds for the sought invention in order to improve pattern collapse and line edge roughness. The resin of Kaneko et al. performed using the above method and the above specified chain transfer agent and initiator is expected to result in a resin containing no cyano group at a resin end of instant claim 29, absent any evidence to the contrary.
Claim 30 is rejected under 35 U.S.C. 103 as being unpatentable over Kaneko et al. (U.S. 2010/0104974) in view of Funaki et al. (U.S. 6,692,889).
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] 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 of instant claim 30. Kaneko et al. also teaches the polymerization method includes a method of performing the polymerization by heating a solution containing monomers, a polymerization initiator and a chain transfer agent of formula (CT) (batch polymerization), and a method of performing the polymerization while adding a solution containing monomers to a heated solution (dropping polymerization), but a dropping polymerization method is preferred in view of production stability. The monomers, polymerization initiator and chain transfer agent may be separately added to the reaction system or may be added as a mixture. In the case of separately adding these to the reaction system, the addition time may be the same or different, and the addition initiating time may be staggered. In the present invention, the reaction system may be a reaction solvent itself or may be a reaction solvent where some selected from monomers, a polymerization initiator and a chain transfer agent are previously added. More specifically, in the present invention, monomers may be polymerized using a reaction solvent itself as the reaction system while adding monomers, a polymerization initiator and a chain transfer agent thereto, or after preparing a reaction system by previously adding some selected from monomers, a polymerization initiator and a chain transfer agent to a reaction solvent, monomers may be polymerized while adding the remaining monomers, polymerization initiator and chain transfer agent thereto. In particular, it is preferred to prepare a reaction system by adding the entire amount of a chain transfer agent used and depending on the case, adding some of monomers and a polymerization initiator and then add the remaining monomers and polymerization initiator thereto [0227]. Kaneko et al. further teaches as for the polymerization initiator, a commercially available radical initiator (e.g., azo-based initiator, peroxide) can be used. The radical initiator is preferably an azo-based initiator, and an azo-based initiator having an ester group, a cyano group or a carboxyl group is preferred. Preferred examples of the initiator include dimethyl 2,2'-azobis(2-methylpropionate) [0228]. Kaneko et al. also teaches the bottom repeating unit in resin (RA-5) is a specific example of formula (I’), specifically the following [0111]:
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[0111] wherein Xa1 is the same meaning as Xa1 in formula (I’) [0111] which is a hydrogen atom, an alkyl group, a cyano group or a halogen atom [0099] which is structurally similar to a polymerization unit represented by Formula (a4) of instant claim 30 except p is 0 instead of 1 to 3.
Kaneko et al. does not explicitly teach the ring can be substituted, i.e. p is 1 to 3.
However, Funaki et al. teaches a polymeric compound which includes at least one monomer unit selected from among the formulae (I), (II), (III) and (IV) [col 2 lines 29-32] in which formula (I) is the following:
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[col 2 line 35] wherein R1 is a hydrogen atom or a methyl group, R2 and R3 are the same or different and are each a hydrogen atom, a hydroxyl group or a --COOR4 group, where R4 is a t-butyl group, a 2-tetrahydrofuranyl group, a 2-tetrahydropyranyl group or an 2-oxepanyl group [col 3 lines 18-22] such the following seen in Examples 1 and 5:
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[col 39 line 30] and
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[col 41 line 50] in which the left repeating unit is equivalent to Kaneko’s formula (I’) and the right repeating unit is equivalent to a polymerization unit represented by Formula (a4) of instant claim 30 when R is an alkyl group having 1 carbon atom, A is a single bond, Z1 is a cycloalkane ring, p is 1 where Ra is a hydroxy group, and n is 1 where R7 is -COORc where Rc is a tertiary hydrocarbon group. Funaki et al. also teaches the present inventors found that, when a polymer containing a monomer unit having an adamantane skeleton with a specific structure is used as a photoresist resin, the resulting photoresist resin has satisfactory etching resistance, in addition to excellent transparency, alkali-solubility and adhesion [col 2 lines 20-26].
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 a substituent on the adamantane ring as taught by Funaki et al. and arrive at the instant claims through routine experimentation of substituting equally suitable groups for the sought invention in order to achieve optimum etching resistance, transparency, alkali-solubility, and adhesion. The resin of Kaneko modified by Funaki performed using the above method and the above specified chain transfer agent and initiator is expected to result in a resin containing no cyano group at a resin end of instant claim 30, absent any evidence to the contrary.
Response to Arguments
Applicant's arguments filed February 13, 2026 have been fully considered but they are not persuasive. Applicant argues regarding the 103 rejection over Kaneko, Kaneko fails to disclose or suggest the claimed polymerization units. Further, the cited reference or the knowledge in the art provides no proper reason or rationale that would allow one of ordinary skill in the art to arrive at the claimed invention.
The Examiner respectfully disagrees. Kaneko et al. teaches repeating units of formula (I’), specifically the bottom repeating unit of resin (RA-5) [page 43] which is equivalent to Applicant’s formula (a4). Kaneko et al. also teaches the living radical polymerization method can include initiators and chain transfer agents which do not contain a cyano group [0228] and [0225] respectively. Therefore, the instant claims continue to be obvious over Kaneko et al. based on the entire disclosure and routine experimentation in the art.
Due to the amendment to instant claim 10, the objection has been withdrawn.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. U.S. 2015/0185610, U.S. 2015/0338744, and U.S. 2016/0048082.
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 8:00-4:30 EST M-F.
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/Anna Malloy/Examiner, Art Unit 1737
/MARK F. HUFF/Supervisory Patent Examiner, Art Unit 1737