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 5 are objected to because of the following informalities:
Claim 2 recites “… and a bond between M12 and R13 is an M12-carbon single bond” in line 3. Claim 2 depends from claim 1, wherein -OR12 may be *-M12(R13)m(OR14)(3-m) as an option for R12. Claim 1 does not require the presence of a M12-R13 bond, and claim 2 does not positively claim that R12 is *-M12(R13)m(OR14)(3-m), requiring the presence of a M12-R13 bond. It appears as though applicant intended to include a limitation requiring R12 to be *-M12(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 M12 and R13 is an M12-carbon single bond.
Claim 5 recites similar language and recites “when R11 and R13 are each … and/or R12 and R14”. As noted above, *-M12(R13)m(OR14)(3-m) is an option for R12, but is not required nor is claim 5 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 *-M12(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 § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 9-12, 16, and 17 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
The claims present limitations to a polymer comprising at least one of Formula 2. Formula 2 requires “X21” which is defined as being at least one of a halogen, R31SO3, R31CO2, R31PO4, or NO3. However, the definitions of X21 aside from a halogen atom are confusing and it is unclear as to what structure applicant is claiming.
The only example of the structure includes a halogen atom ([0147], [0151]), and it is unclear as to how the remaining structures are formed. As written, it appears as though R31 (a hydrocarbon group, [0131]) is bonded to the main structure, however that would leave the end group (SO3, CO2, PO4, and the group without R31, NO3) as charged, and the specification does not teach that the structure is charged monomer having an anionic group (see claim 1 and specification [0131]).
The examples of the structures are drawn below (R1 is the instantly claimed R31), but the specification and claims do not provide definitions which are clear and for one of skill in the art to prepare the polymer.
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Should the applicant intend for the group to attach at the other end, an example appears below (however the NO3 would be the same).
Or does applicant intend and acidic group:
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For purposes of examination, the claim will be interpreted in the broadest reasonable interpretation, which includes any of the above structures for Formula 2.
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) 1-10, 12-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kudo et al (2020/0257195) in view of Endo et al (JP 62-192412 and its machine translation).
Kudo et al disclose a photoresist composition comprising an organometallic complex having a structure falling within the scope of the instant Formula 1.
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Wherein in the formula, L is a ligand other than -OR1, and may be a monodentate ligand, and may include (meth)acrylate (which meets the limitations for the instant R11 for a C1 to C30 hydrocarbon group optionally containing one or more hetero atoms), and R1 is alkyl, cycloalkyl, aryl, heteroaryl, vinyl ([0039]), which falls within the scope of the instant R12.
In the formula x may be 0 to 6. Te meets the limitations of the instant M11. When x is 1 and L is a (meth)acrylate group, the instant Formula 1 is met. The compounds as exemplified are low molecular weight compounds and have molecular weights of less than 3,000 g/mol (see examples; instant claim 3). Compounds as discussed above for the broader teachings of the reference have a structure similar to that of the instant 1-1, for examples, wherein R11a alkyl, and OR12a to care alkoxy, with M being Te (instant claim 4, 6).
Regarding claims 2 and 5, the claims present limitations to M11 and R11 (claim 2) and R11 and R12 (claim 5), and to M12, R13, and R14 when present. In the reference formulas, R12 is alkyl, not *-M12(R13)m(OR14)(3-m), therefore M12, R13, and R14 are not present in claims 2 and 5. Therefore, the reference formula includes a structure wherein M11 and 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. Additionally, reference L, instant R11 can be (meth)acrylate, therefore R11 can be *-(L11)a11-X11, wherein a11 is 1, with L11 is -C=O, and X11 alkoxy (-C(=OO-O-alkyl).
The reference further teaches that the composition comprises resin (resist material), a solvent, an acid generator, an acid crosslinking agent, a polymerization initiator, a solvent, and other known and common resist components ([0050]; instant claim 15).
Examples of resist resins include phenolic and naphthol derivatives, novolac resins, and (meth)acrylic acid or derivatives thereof, but not limited thereto ([0051]).
Kudo et al fails to specifically disclose the resist resin, however, Endo et al disclose a resin comprising a vinyl aromatic monomer comprising a unit meeting the limitations of the instant formula 1, wherein R (the instant R21) is H or methyl, the instant R23 and R24 are each H, the instant R22 is H with b22 is 4, and the instant X21 is a sulfonium salt as part of a saturated ring (abstract, examples, page 101, column 1; formula 2-1, 20; instant claims 1, 8, 12, 16, 17):
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The ring meets the limitations of the instant claim 6, wherein X21 is sulfonium. Examples include a PF6- anion (Table 1(b), abstract) as required by the instant claim 7.
The additional monomers include a spiro-orthoester which is not acid-labile but crosslinks under action of light, and an additional monomer such as a methyl(meth)acrylate and other (meth)acrylates without tertiary carbon atoms or other acid-labile groups which are known to change under action of acid (instant claims 7).
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 Endo et al, choosing as the third monomer, those as taught by the reference and discussed above which have structures falling within the scope of the instant claims. The resultant composition would comprise an organometallic compound of formula 1 and a monomer of formula 2.
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 Kudo et al, choosing as the resin, that comprising the vinyl monomer of Endo et al taught to have improved crosslinking.
With respect to the instant claim 13, the primary reference teaches that the combined amount of the Te compound and the resin is 1 to 99 content ratio of the solid content to achieve desired performance including sensitivity, resolution, and developability ([0075]), and the resin is present in an amount of 1000 parts by mass or less, preferably 500 parts or less, 200 parts or less, most preferably 100 part to 100 parts by mass of the compound ([0051], [0052]). The broad range of parts by mass would fall within the scope of the parts by weight as set forth by the instant claim 13, wherein the organometallic compound is included in an amount of 10 to 1000 parts to 100 parts of the polymer (instant claim 13).
With respect to the instant claim 14, the references are silent with respect to the MW of the polymer, however, given it is known that the MW of a polymer affects the properties of the composition comprising it, one of ordinary skill in the art would have arrived at the claimed molecular weight through routine experimentation and optimization of the material properties such as sensitivity, developability, and resolution.
The composition is used in a pattern formation method including applying the composition and pre-baking to form the layer, exposing the resist layer to light including DUV, EUV, ion beam, and x-rays, then developing the resist, ebeam exposure in examples ([0080]-[0083], [0128]; instant claims 18, 19). 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 20).
Claim(s) 1-9, 12-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kudo et al in view of Mori et al (2005/026018).
Kudo et al has been discussed above. The reference fails to specifically disclose the resist resin, however, Mori et al disclose a resin comprising a vinyl aromatic monomer comprising a unit meeting the limitations of the instant formula 2.
Mori et al disclose a polymer comprising a monomer falling within the scope of the instant Formula 2, wherein the polymer does not comprise a unit which is acid-labile (instant claim 7) usable in polymer in heat and/or light sensitive materials.
In the exemplified compounds, R21 is H, R22 is H, R23 and R24 are H, and X21 is Cl or
-CO2R31, with R31 being aryl or methyl (instant claims 1, 8, 9, 12, 16; formulas 2-2 and 20 also).
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Furthermore, the reference teaches that the -CH2- group may have a -OCO-hydrocarbon or hlaogen substituent, but teaches more broadly that other substituents are equivalent to those and may be repalced for the -OCO- and halogen groups. These includecarboxylic acid and sulfonic acid groups, which meet R18CO2H and R18SO3H ([0047]-[0052]).
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 Kudo et al, choosing as the resin, that comprising the vinyl monomer, that known for use in heat and/or light sensitive materials as taught by Mori et al.
With respect to the instant claim 13, the primary reference teaches that the combined amount of the Te compound and the resin is 1 to 99 content ratio of the solid content to achieve desired performance including sensitivity, resolution, and developability ([0075]), and the resin is present in an amount of 1000 parts by mass or less, preferably 500 parts or less, 200 parts or less, most preferably 100 part to 100 parts by mass of the compound ([0051], [0052]). The broad range of parts by mass would fall within the scope of the parts by weight as set forth by the instant claim 13, wherein the organometallic compound is included in an amount of 10 to 1000 parts to 100 parts of the polymer (instant claim 13).
With respect to the instant claim 14, the references are silent with respect to the MW of the polymer, however, given it is known that the MW of a polymer affects the properties of the composition comprising it, one of ordinary skill in the art would have arrived at the claimed molecular weight through routine experimentation and optimization of the material properties such as sensitivity, developability, and resolution.
The composition is used in a pattern formation method including applying the composition and pre-baking to form the layer, exposing the resist layer to light including DUV, EUV, ion beam, and x-rays, then developing the resist, ebeam exposure in examples ([0080]-[0083], [0128]; instant claims 18, 19). 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 20).
Claim(s) 1-9 and 12-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kudo et al in view of Matsui et al (JP 64-9207 [01-009207] and its machine translation).
Kudo et al has been discussed above. The reference fails to specifically disclose the resist resin, however, Matsui et al disclose a resin comprising a vinyl aromatic monomer comprising a unit meeting the limitations of the instant formula 2.
Matsui et al disclose a crosslinkable fluorinated styrene polymer comprising no group having the property of structure change by action of acid, having a monomer of strcuture falling within the scope of the instant formula 2 (and formulas 2-2, 20).
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The examples of the monomers include those wherein R21 is hydrogen or methyl, R23 and R24 are hydrogen, and X21 is -CH2-O-CO-“R”, wherein “R” is an alkyl group. The structure is of -R31-OCO-R, meeting the limitations of the instant claims 1, 7-9, 12, and 16.
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 Matsui et al, choosing as the polymer, that comprising a unit as described above, which also falls within the scope of the instant formula 2.
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 Kudo et al, choosing as the resin, that comprising the vinyl monomer, that known for use as a crosslinking resin in various materials as taught by Matsui et al.
With respect to the instant claim 13, the primary reference teaches that the combined amount of the Te compound and the resin is 1 to 99 content ratio of the solid content to achieve desired performance including sensitivity, resolution, and developability ([0075]), and the resin is present in an amount of 1000 parts by mass or less, preferably 500 parts or less, 200 parts or less, most preferably 100 part to 100 parts by mass of the compound ([0051], [0052]). The broad range of parts by mass would fall within the scope of the parts by weight as set forth by the instant claim 13, wherein the organometallic compound is included in an amount of 10 to 1000 parts to 100 parts of the polymer (instant claim 13).
With respect to the instant claim 14, the references are silent with respect to the MW of the polymer, however, given it is known that the MW of a polymer affects the properties of the composition comprising it, one of ordinary skill in the art would have arrived at the claimed molecular weight through routine experimentation and optimization of the material properties such as sensitivity, developability, and resolution.
The composition is used in a pattern formation method including applying the composition and pre-baking to form the layer, exposing the resist layer to light including DUV, EUV, ion beam, and x-rays, then developing the resist, ebeam exposure in examples ([0080]-[0083], [0128]; instant claims 18, 19). 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 20).
Claim(s) 1-10 and 12-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Moon et al (JP2020-021071 and its machine translation) in view of Endo et al.
Moon et al disclose a resist composition comprising an organometallic compound falling within the scope of the instant formula 1.
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R1 is alkyl, cycloalkyl, alkenyl, aryl,, and arylalkyl, and R2 to R4 are each -ORa or -OC(=O)O-Rb, similar to that of general formula 1, wherein ,-(L)n-(R1) with Ra being a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, or a combination thereof, and
Rb being a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, It is a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, or a combination thereof.
Instant R11 is R1, with instant n being 1, and instant (4-n) being 3, and R2-R4 being instant -OR1a or -O-C(=O)-Rb (see examples), which equates to the instant -OR12 (instant claims 1, 4).
The exemplified compounds fall within the scope of the instant formula:
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Regarding claims 2 and 5, the claims present limitations to M11 and R11 (claim 2) and R11 and R12 (claim 5), and to M12, R13, and R14 when present.
In the reference formulas, R12 is alkyl, not *-M12(R13)m(OR14)(3-m), therefore M12, R13, and R14 are not present in claims 2 and 5. Therefore, the reference formula includes a structure wherein M11 and 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. For the examples, instant R12 is alkyl, alkenyl, wherein R12 may be *-(L12)a12-X12, with a12 being 1, L12 being -C=O, and X12 being -O-(alkyl or alkenyl).
The exemplified compounds meet the limitations of the instant claim 6 for 1-1. The exemplified compounds have molecular weights of less than 3000 g/mol (instant claim 3).
The content of the compound in the material is 0.01 to 10 % by mass based on the total mass of solids in the composition ([0055]).
The reference material further includes a resin preferably having a molecular weight of 500 to 20,000 ([0062]; instant claim 14).
The resin may include a resin, such as a phenolic resin, at least having an aromatic moiety as a preferred, but non-limiting examples ([0060]).
The resin is included in an amount of 0.1 to 50% by mass based on the total mass of the composition ([0063]).
With respect to the instant claim 13, given the teachings of the reference for the broad amounts of compound and resin taught by the reference, one of ordinary skill in the art would have arrived at the claimed amount of compound to resin, wherein the compound is present in an amount of 10 to 1000 parts by weight of 100 parts of the resin through routine experimentation and optimization of resist composition properties including etching resistance and heat resistance ([0064]; instant claim 13).
The resist composition further includes a solvent, and may includes additional known additives such as a surfactant, a leveling agent, a crosslinking agent ([0065]-[0069]; instant claim 15).
The method of patterning includes applying the resist to a substrate, drying/ pre-baking to form a film, exposing to preferably DUV, EUV, or ebeam radiation, post-baked, developed, then post-processing the substrate and/or under layers ([0070]-[0092]; instant claims 18-20).
Moon et al fails to specifically disclose the resist resin, however, Endo et al, as discussed above, disclose a resin comprising a vinyl aromatic monomer comprising a unit meeting the limitations of the instant formula 1, (instant claims 1, 8, 12, 16, 17):
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Given the teachings of the references, 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 Moon et al, choosing as the resin, that comprising the vinyl monomer of Endo et al taught to have improved crosslinking.
The resultant material and method would also meet the limitations of the instant claims.
Claim(s) 1-9 and 12-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Moon et al in view of Mori et al.
Moon et al fails to specifically disclose the resist resin, however, Mori et al, as discussed above,disclose a polymer comprising a monomer falling within the scope of the instant Formula 2, wherein the polymer does not comprise a unit which is acid-labile (instant claim 7) usable in polymer in heat and/or light sensitive materials.
In the exemplified compounds, R21 is H, R22 is H, R23 and R24 are H, and X21 is Cl or
-CO2R31, with R31 being aryl or methyl (instant claims 1, 8, 9, 12, 16; formulas 2-2 and 20 also).
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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 Moon et al, choosing as the resin, that comprising the vinyl monomer, that known for use in heat and/or light sensitive materials as taught by Mori et al.
Claim(s) 1-9 and 12-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Moon et al in view of Matsui et al.
Moon et al has been discussed above. The reference fails to specifically disclose the resist resin, however, Matsui et al disclose a resin comprising a vinyl aromatic monomer comprising a unit meeting the limitations of the instant formula 2.
Matsui et al disclose a crosslinkable fluorinated styrene polymer comprising no group having the property of structure change by action of acid, having a monomer of strcuture falling within the scope of the instant formula 2 (and formulas 2-2, 20).
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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 Moon et al, choosing as the resin, that comprising the vinyl monomer, that known for use as a crosslinking resin in various materials as taught by Matsui et al.
Allowable Subject Matter
Claim 11 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The cited references of record fail to fairly teach or suggest to one of ordinary skill in the art to prepare the material of claim 1, wherein the polymer comprises a unit of formula 2-1 having a salt, and 2-2 having a halogen, , R31SO3, R31CO2, R31PO4, or NO3.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Moon et al (2020/0041896) is cited for its teaching of a similar compound, however the reference formula requires R1 o R3 to be -OR and L may be a linking group comprising a carbon atom, but must comprise a metal atom, not a hetero atom Instant R12 may comprise an additional meal atom, and R13 and (OR14) but .there is no group equating to R11.
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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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Niki Bakhtiari can be reached at 571-272-3433. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMANDA C. WALKE/Primary Examiner, Art Unit 1722