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 .
Claim Objections
Claims 2 and 4 are objected to because of the following informalities:
The instant claim 2 recites “… and a bond between Sn and R13 is an Sn-C single bond” in line 3. Claim 2 depends from claim 1, wherein -OR12 may be *-Sn(R13)m(OR14)(3-m) as an option for R12. Claim 1 does not require the presence of a Sn-R13 bond, and claim 2 does not positively claim that R12 is *-Sn(R13)m(OR14)(3-m), requiring the presence of a Sn-R13 bond. It appears as though applicant intended to include a limitation requiring R12 to be *-Sn(R13)m(OR14)(3-m), but it is not currently defined in that manner. For purposes of examination, the claim will be interpreted as when present and a bond between Sn and R13 is an Sn-C single bond. Appropriate correction is required.
Claim 4 recites similar language and recites “when R11 and R13 are each … and/or R12 and R14”. As noted above, *-Sn(R13)m(OR14)(3-m) is an option for R12, but is not required nor is claim 4 written such that it must be present. Similar to claim 2 above, It appears as though applicant intended to include a limitation requiring R12 to be *-Sn(R13)m(OR14)(3-m), thus the structure would then include each of R11 to R14, but it is not currently defined in that manner. For purposes of examination, the claim will be interpreted as when present R13 and R14 are the groups as set forth in lines 2-5 of claim 5. Appropriate correction is required.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1-7 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Mack (2,745,820).
Mack discloses a resin composition comprising tin monoalkoxide compound and a resin.
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The monotin alkoxide compound has a structure falling within the scope of the instant formula 1, wherein the instant n is 3, R (instant R11) is alkyl, preferably butyl, ethyl, and R’ (instant R12) is alkyl, cyclo alkyl, or aryl, with benzene, ethyl, cyclohexyl (see examples 1-6), meeting the limitations of the instant claims 1 and 2, wherein Sn and R11 is a Sn-carbon bond. The compounds have molecular weights of less than 3,000 g/mol (instant claim 3).
With respect to the instant claims 2 and 4, the claims present limitations to R11, and to R13 when present. In the reference formulas, R12 is alkyl, not *-Sn(R13)m(OR14)(3-m), therefore R13 is not present in claim 2 or claim 4. Therefore, the reference formula includes a structure wherein Sn and R11 is a metal-carbon single bond X11 being alkyl, cycloalkyl, aryl, alkenyl.
The compound meets the limitations of the instant claim 4 wherein a11 is 0, and instant formula 1-3, wherein instant n is 3m and (4-n) is 1 (having one -OR12 group), thus meeting the limitations of the instant claim 5.
The resin is a halogen-containing resin including vinyl chloride, chlorinated styrenes (column 2, line 68 to column 3, line 11). The instant specification teaches that the radical generating group X may be halogen bonded to a carbon atom, which the monomers above meet, thus the reference teaches a polymer comprising a unit as described for the claimed polymer (see examples 1-6; instant claims 1, 6, and 7).
Claim(s) 1-8, 10-14, and 17-20 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Naito et al (11,347,147).
Natio et al disclose a resist composition comprising a metal-containing onium salt compound and a resin, wherein the salt includes the following structure:
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In the formula, M is preferably Sn (all exemplified compounds include Sn), the instant R11 is cyclic hydrocarbon group having a heteroatom or alkyl, n is 4, wherein OR12 is not present (column 5, lines 8-43). The structure therefore falls within the scope of the instant claims 1, and 5, wherein the structure of the instant 1-4.
With respect to the instant claims 2 and 4, the claims present limitations to R11, and to R13 when present. In the reference formulas, R12 is alkyl, not *-Sn(R13)m(OR14)(3-m), therefore R13 is not present in claim 2 or claim 4. Therefore, the reference formula includes a structure wherein Sn and R11 is a metal-carbon single bond X11 being alkyl, cycloalkyl, aryl, alkenyl. In the reference formula, n is 4, therefore 4-n is 0, and R12 is not present, and the structure meets the limitations of the instant claim 2.
The compound meets the limitations of the instant claim 4 wherein a11 is 0.
The compounds have molecular weights of less than 3,000 g/mol as required by the instant claim 3.
The resin includes a unit comprising a lactone ring and a unit comprising and -OH group (see exemplified polymers A-1 to A-3).
Each of these units includes a group falling within the scope of the instant radical generating unit or radical accepting unit, specifically wherein the lactone ring group includes an oxygen atom having two lone-pairs of electrons (instant claims 10, 11, RA1 in claim 13 wherein Cy is cyclopentyl and Y is C=O), and the -OH radical generating group includes a C-X single bond, wherein X is -OH and further includes an oxygen atom (instant claims 5 and 6, also claim 10 as -OH is electron accepting). Regarding claim 8, the adamantyl ring include and is adjacent to the carbon atom also bond to the -OH group.
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Regarding the structures of the instant claim 14, the lactone-containing unit meets the limitations of the instant formula 2-5, wherein R’ is methyl or H, n9 is 1, L9 is -C(=O)O-, L7 is -CH2-, n7 is 1, and L8 is a single bond with n8 being 1,
The method of patterning includes applying the composition to a substrate, pre-baking/ drying, exposing to DUV, EUV, or electron beam (column 23, lines 6-29), post-baking, and developing to remove the unexposed areas (examples; instant claims 17, 18, and 20).
While the reference doesn’t specifically teach that chemical bonds are formed between the organometallic compound and the polymer, given that the compounds are the same and the method includes the same steps, one of ordinary skill in the art would have expected the material to form chemical bonds as instantly claimed given the similarity in the material and methods absent evidence to the contrary (instant claim 19).
Claim Rejections - 35 USC § 103
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.
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.
Claim(s) 10, 11, and 14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Mack.
Mack has been discussed above, and further teaches additional monomers for the resins which include radical accepting groups having a lone-pair electron donating group and/or electron donating group wherein additional monomers include acrylonitrile and vinyl acetate (see column 2, line 65 to column 3, line 11, examples 1 and 2), which include lone pairs of electrons, and comprise a nitrogen atom and oxygen atom, respectively, thus meeting the limitations of the instant claims 10 and 11.
Therefore, given the teachings of the reference, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the instant invention to prepare the material of Mack, choosing to include a polymer/ resin having a unit with a radical accepting group such as vinyl acetate or acrylonitrile.
Claim(s) 1-7 and 17-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Moon et al (2021/0333708).
Moon et al disclose a resist composition comprising an organotin compound having a structure falling within the scope of the instant formula 1.
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In the formula, the instant R11 is alkyl, cycloalkyl, alkenyl, aryl, and each of R2 to R4 (instant -OR12) is -ORa or -OC(=O)Rb, with Ra and Rb being alkyl, cycloalkyl, alkenyl, aryl, with the instant n being 1. Exemplified/ claimed compounds include the following, wherein the molecular weights are less than 3,000 g/mol (instant claim 3), and R11 includes a11 as 0, with X11 being alkyl (preferably), thus meeting the limitations of the instant claim 4, and claim 5 when the formula is 1-1.
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Furthermore regarding claims 2 and 4, the claims present limitations to R11 (claim 2) and R11 and R12 (claim 4), and
R13, and R14 when present. In the reference formulas, R12 is alkyl, not *-Sn(R13)m(OR14)(3-m), therefore R13, and R14 are not present in claims 2 and 4. Therefore, the reference formula includes a structure wherein R11 is a metal-carbon single bond, and wherein R11 and R12 are *-(L11)a11-X11 and *-(L12)a12-X12, with a11 and a12 being 0 and X11 and X12 being alkyl, cycloalkyl, aryl, alkenyl.
The reference further teaches that the composition may comprise a resin, which may be a phenol-based resin, but is not limited thereto. The exemplified aromatic rings do not include -OH groups, but the group would comprise at least one to be considered a phenol ([0053]-[0055]). The resin/ polymer having the phenol group would meet the limitations of the instant claim 1 for a polymer having a radical generating group, wherein there would be a -C-X bond, with X being oxygen as exemplified in the example in the instant specification. The polymer would meet the limitations of the instant claims 1, 6, and 7.
The method of patterning the resist includes applying the composition to a substrate, drying/pre-baking to form the film, exposing to EUV or ebeam radiation, post-baking, developing the resist to remove the unexposed portion ([0074]-[0085]; instant claims 17, 18, and 20). While the reference doesn’t specifically teach that chemical bonds are formed between the organometallic compound and the polymer, given that the compounds are the same and the method includes the same steps, one of ordinary skill in the art would have expected the material to form chemical bonds as instantly claimed given the similarity in the material and methods absent evidence to the contrary (instant claim 19).
Claim(s) 15 and 16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Naito et al.
Naito et al has been discussed above. The reference further teaches that the acid-reactive compound (which may be a polymer as preferred and used in examples) may be a polymerizable monomer or crosslinkable monomer having a polymerizable group. These monomers may include groups which change solubility in developing solution, including -OH groups. Therefore, the monomer as suggested by the reference may include both a -OH (radical generating group) and a polymerizable group, thus meeting the limitations of the instant claims 15 and 16 (column 19, line 18 to column 20, line 47).
Given the teachings of the reference, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the instant invention to prepare the material of Naito et al, choosing as the acid-reactive additive, a monomer having an -OH group and a polymerizable group as taught by the reference. The resultant material and compound would meet the limitations of the instant claims.
Claim(s) 9 and 14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Naito et al in view of Hatakeyama et al (9,023,587).
Naito et al has ben discussed above. The reference teaches a resist polymer having a variety of non-limiting common resist monomers. The reference teaches that a monomer having a hydroxyl group may be included, but fails to specifically disclose a unit having the structure of instant RG.
Hatakeyama et al disclose a resist composition and polymer wherein the polymer comprises a unit having a group similar to the instant RG, in combination with othr known monomers, such as those disclosed by Naito et al (may include lactone-containing (meth)acrylates, cyclic-containing (meth)acrylates having -OH groups, acid-generating units; column 20, line 56 to column 21, line 20).
The unit includes a phenyl or naphthyl group, with a -C(RR’-X1 group, and teaches the equivalence to those groups to the hydroxy-adamantyl group as disclosed by Naito et al.
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In the monomers of the reference each of instant R and R’ are H or alkyl (or join to form a ring), and X1 is -OH. The inclusion of the unit to the polymer improves etch resistance of the resist pattern for EUV and Ebeam lithography. The compound meets the limitations of the instant Formula 2-5 when L7 is CH, n7 is 1, R” is H or methyl, L8 is a single bond with n8 being 1, L9 is aryl or -C(=O)O-aryl, and Z1 is -OH.
Therefore, given the teachings of the references, it would have been obvious to one of oridnary skill in the art prior to the effective filing date of the instant invention to prepare the material of Naito et al, choosing as the -OH group containing unit, that as taught by Hatakeyama et al to improve etch resistance, especially in EUV and Ebeam lithography.
Claim(s) 9 and 14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Moon et al in view of Hatakeyama et al.
Both references have been discussed above. Moon et al teach that known resist resins, including those having units comprising aromatic ring having -OH groups may be included, but fails to specifically teach a unit comprising the instant formula RG.
Hatakeyama et al teach a unit having a structure comprising RG, and teaches that the inclusion of the unit and resin improves etch resistance of EUV and Ebeam resist lithography.
Therefore, given the teachings of the references, it would have been obvious to one of oridnary skill in the art prior to the effective filing date of the instant invention to prepare the material of Moon et al, choosing as the -OH group containing unit, that as taught by Hatakeyama et al to improve etch resistance, especially in EUV and Ebeam lithography.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Choi et al (2022/0334474) disclose a resist comprising a metal compound and a polymer, wherein the resin comprises a hydroxystyrene-based polymer meeting the limitations of the instant claim 1 for the radical generating and/or accepting group. The metal is preferably tin, and the ligand L may be halogen, alkyl, alkoxy, independently, however the reference teaches that the ligands are preferably all alkoxy groups and does not provide clear motivation to chose at least one to be alkyl
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMANDA C WALKE whose telephone number is (571)272-1337. The examiner can normally be reached Monday to Thursday 5:30am to 4pm.
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/AMANDA C. WALKE/ Primary Examiner, Art Unit 1722