DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-20 are pending.
The foreign priority document No. 10-2023-0128482 filed on September 25, 2023 in the Republic of Korea has been received and it is acknowledged.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-14 and 17-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 9, and 17-20 of copending Application No. 18/769,750 (US 2025/0237945). Although the claims at issue are not identical, they are not patentably distinct from each other because both applications claim the same organometallic compounds, the same resist composition, and the same method of forming a pattern.
The copending Application No. 18/769,750 claims a resist composition comprising an organometallic compound (claim 1), which may be represented by the formula:
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(claim 9).
This compound is an organometallic compound of Formula 1-2 in claims 1, 3-5, and 9 of the instant application, wherein M11 is tin(Sn), b11=2, b12=2, Q11 and Q12 are substituted C6 aryl groups, the substituents of the C6 aryl groups being C4 alkyl groups, the two adjacent groups Q11 and the two adjacent groups Q12 are bonded to each other to form condensed rings, R11 and R12 are hydrogen atoms, Y11 and Y12 are O(C=O), X11 and X12 are linear C2 hydrocarbons.
The compound above has a Sn-C bond dissociating energy of 21.64 kcal/mol (see par.0120) of the instant application. This value is within the range of claim 2 of the instant application.
The compound above is an organometallic compound of Formula 1-2 in claims 6 and 7 of the instant application, wherein *-C(Q11)b11(R11)(3-b11) is represented by the formula 2-11 and *-C(Q12)b12(R12)(3-b12) is represented by the formula 2-23, wherein R11c and R12c are hydrogen atoms, Q11a, Q11b, Q12a, and Q12b are substituted C6 aryl groups, the substituents of the C6 aryl groups being C4 alkyl groups, a11=1, a12=1, L11 and L12 are single bonds.
The compound above is an organometallic compound of Formula 1-2 in claims 8 and 10 of the instant application, wherein *-C(Q11)b11(R11)(3-b11) is represented by the formula 3-11 and *-C(Q12)b12(R12)(3-b12) is represented by the formula 3-21, wherein R11c and R12c are hydrogen atoms, A31 and A32 are C6 aryl groups, a11=1, a12=1, L11 and L12 are single bonds, b31=1, b32=1, R31 and R32 are C4 alkyl groups.
The compound above is one of the compounds in claim 11 of the instant application.
The resist composition in claims 1 and 9 of the copending Application No. 18/769,750 is equivalent to the resist composition in claim 12 of the instant application.
The copending Application No. 18/769,750 claims that the resist composition comprises the organometallic compound and an additive (claim 1), so it meets the limitations of claims 13 and 14 of the instant application.
The copending Application No. 18/769,750 further claims a method of forming a pattern comprising the steps of: applying the resist composition onto a substrate to form a resist film, exposing at least a portion of the resist film to high-energy rays to provide an exposed resist film, and developing the exposed resist film using a developer (claim 17), same as in claim 17 of the instant application.
The copending Application No. 18/769,750 further claims that the exposing is performed with deep ultraviolet rays (DUV), extreme ultraviolet rays (EUV), electron beams (EB) (claim 18), same as in claim 18 of the instant application.
The copending Application No. 18/769,750 further claims that the organometallic compound is subjected to a condensation reaction based on exposing the film (claim 19). The condensation reaction bonds molecules of organometallic compounds, as required in claim 19 of the instant application.
The copending Application No. 18/769,750 further claims that the exposed resist film includes an exposed portion and a non-exposed portion, and in the developing step the non-exposed portion is removed (claim 20), same as in claim 20 of the instant application.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-18 and 20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, 11, 15-17, and 20 of copending Application No. 19/062,708 (US 2026/0063990). Although the claims at issue are not identical, they are not patentably distinct from each other because both applications claim the same organometallic compounds, the same resist composition, and the same method of forming a pattern.
The copending Application No. 19/062,708 claims a resist composition comprising an organometallic compound (claim 1), which may be represented by the formula:
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(claim 5).
This compound is an organometallic compound of Formula 1-2 in claims 1, 3-5, and 9 of the instant application, wherein M11 is tin(Sn), b11=2, b12=2, Q11 and Q12 are substituted C6 aryl groups, the substituents of the C6 aryl groups being C4 alkyl groups, the two adjacent groups Q11 and the two adjacent groups Q12 are bonded to each other to form condensed rings, R11 and R12 are hydrogen atoms, Y11 and Y12 are O(C=O), X11 and X12 are linear C2 hydrocarbons.
The compound above has a Sn-C bond dissociating energy of 21.64 kcal/mol (see par.0120) of the instant application. This value is within the range of claim 2 of the instant application.
The compound above is an organometallic compound of Formula 1-2 in claims 6 and 7 of the instant application, wherein *-C(Q11)b11(R11)(3-b11) is represented by the formula 2-11 and *-C(Q12)b12(R12)(3-b12) is represented by the formula 2-23, wherein R11c and R12c are hydrogen atoms, Q11a, Q11b, Q12a, and Q12b are substituted C6 aryl groups, the substituents of the C6 aryl groups being C4 alkyl groups, a11=1, a12=1, L11 and L12 are single bonds.
The compound above is an organometallic compound of Formula 1-2 in claims 8 and 10 of the instant application, wherein *-C(Q11)b11(R11)(3-b11) is represented by the formula 3-11 and *-C(Q12)b12(R12)(3-b12) is represented by the formula 3-21, wherein R11c and R12c are hydrogen atoms, A31 and A32 are C6 aryl groups, a11=1, a12=1, L11 and L12 are single bonds, b31=1, b32=1, R31 and R32 are C4 alkyl groups.
The compound above is one of the compounds in claim 11 of the instant application.
The resist composition in claims 1 and 5 of the copending Application No. 19/062,708 is equivalent to the resist composition in claim 12 of the instant application.
The copending Application No. 19/062,708 claims that the resist composition comprises the organometallic compound and an additive (claim 1), so it meets the limitations of claims 13 and 14 of the instant application.
The copending Application No. 19/062,708 further claims that the resist composition further comprises a solvent, such as methyl ethyl ketone (claims 11 and 15). This is an aprotic organic solvent, as required in claims 15 and 16 of the instant application.
The copending Application No. 19/062,708 further claims a method of forming a pattern comprising the steps of: applying the resist composition onto a substrate to form a resist film, exposing at least a portion of the resist film to high-energy rays to provide an exposed resist film, and developing the exposed resist film using a developer (claim 16), same as in claim 17 of the instant application.
The copending Application No. 19/062,708 further claims that the exposing is performed with deep ultraviolet rays (DUV), extreme ultraviolet rays (EUV), X-rays, g-rays, a-rays, or electron beams (EB) (claim 17), same as in claim 18 of the instant application.
The copending Application No. 19/062,708 further claims that the exposed resist film includes an exposed portion and an unexposed portion, and in the developing step the unexposed portion is removed (claim 20), same as in claim 20 of the instant application.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
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.
Claims 1, 3, 4, 6, 7, 9, 12, 13, and 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2020/0348591) in view of Hatakeyama (US 2023/0021453) and in further view of Nemes et al. (“Difluorenylsilanes, -germanes, -stannanes Exhibiting an Unprecedented Parallel Arrangement of the Fluorene Units”).
With regard to claims 1 and 12, Kim et al. teach a photoresist composition which may comprise a compound of Chemical Formula 4:
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, wherein R may be a substituted or unsubstituted C6 to C30 aryl group, Rd, Re, and Rf are independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, or a substituted or unsubstituted C6-C30 aryl group (abstract, par.0012-0017, par.0028-0032).
Kim et al. teach that the “aryl group” may be a fused ring polycyclic functional group (par.0055), but do not teach a compound of formula 1-1 in claim 1.
However, it is well-known in the art that a C6-C30 aryl group may be a fluorenyl group (see par.0056 of Hatakeyama).
Additionally, Nemes et al. show that a fluorenyl group may be bonded to a Sn atom in an organometallic compound (see Chart 2 in the left column of page 1135).
Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to obtain the compound of Chemical Formula 4 of Kim et al. wherein R is a fluorenyl group, Rd, Re, and Rf are independently an unsubstituted C1-C20 alkyl group, an unsubstituted C3-C20 cycloalkyl group, an unsubstituted C2-C20 alkenyl group, an unsubstituted C2-C20 alkynyl group, or an unsubstituted C6-C30 aryl group.
Such compound is an organometallic compound of Formula (1-1) in claim 1, wherein M11 is Sn, b11=2, Q11 is an unsubstituted C6 aryl groups, and the groups Q11 are bonded to each other to form a condensed ring, R11 is hydrogen, Y11, Y12, and Y13 are O(C=O), X11, X12, and X13 are C1-30 monovalent hydrocarbon groups.
The photoresist composition of Kim modified by Hatakeyama and Nemes is the resist composition in claim 12 of the instant application.
With regard to claim 3, a compound of Chemical Formula 4 wherein R is a fluorenyl group, Rd, Re, and Rf are independently an unsubstituted C1-C20 alkyl group, an unsubstituted C3-C20 cycloalkyl group, an unsubstituted C2-C20 alkenyl group, an unsubstituted C2-C20 alkynyl group, or an unsubstituted C6-C30 aryl group is an organometallic compound of Formula (1-1) wherein M11 is Sn.
With regard to claim 4, a compound of Chemical Formula 4 wherein R is a fluorenyl group, Rd, Re, and Rf are independently an unsubstituted C1-C20 alkyl group, an unsubstituted C3-C20 cycloalkyl group, an unsubstituted C2-C20 alkenyl group, an unsubstituted C2-C20 alkynyl group, or an unsubstituted C6-C30 aryl group is an organometallic compound of Formula (1-1) wherein Q11 is an unsubstituted C6 aryl groups, the groups Q11 are bonded to each other to form a condensed ring, and R11 is hydrogen.
With regard to claims 6 and 7, a compound of Chemical Formula 4 wherein R is a fluorenyl group, Rd, Re, and Rf are independently an unsubstituted C1-C20 alkyl group, an unsubstituted C3-C20 cycloalkyl group, an unsubstituted C2-C20 alkenyl group, an unsubstituted C2-C20 alkynyl group, or an unsubstituted C6-C30 aryl group is an organometallic compound of Formula (1-1) wherein *-C(Q11)b11(R11)(3-b11) is represented by the formula 2-11, wherein Q11a and Q11b are unsubstituted C6 aryl groups, a11=1, and L11 is a single bond.
With regard to claim 9, a compound of Chemical Formula 4 wherein R is a fluorenyl group, Rd, Re, and Rf are independently an unsubstituted C1-C20 alkyl group, an unsubstituted C3-C20 cycloalkyl group, an unsubstituted C2-C20 alkenyl group, an unsubstituted C2-C20 alkynyl group, or an unsubstituted C6-C30 aryl group is an organometallic compound of Formula (1-1) wherein X11, X12, and X13 are independently an unsubstituted C1-C20 alkyl group, an unsubstituted C3-C20 cycloalkyl group, an unsubstituted C2-C20 alkenyl group, an unsubstituted C2-C20 alkynyl group, or an unsubstituted C6-C30 aryl group.
With regard to claims 13 and 15, Kim et al. teach that the photoresist composition may comprise the organometallic compound, solvent, and a resin (par.0095), and may further comprises a surfactant, a cross-linking agent, and leveling agent (par.0095).
Therefore, the photoresist composition does not comprise a photoacid generator and meets the limitations of claim 13.
Kim et al. further teach that the solvent is an organic solvent (par.0088), as required in claim 15.
With regard to claim 16, Kim et al. teach that the organic solvent may be an alcohol (par.0088), which are protic organic solvents.
With regard to claim 17, Kim et al. teach a process comprising the steps of:
-forming a photoresist layer (106) by coating the photoresist composition onto a substrate (fig.2, par.0110-0113);
-exposing the photoresist layer (106) with light having high-energy wavelength through a pattern mask (fig.3, par.0114-0115); and
-developing the exposed photoresist layer (fig.4, par.0119).
With regard to claim 18, Kim et al. teach that the light having high-energy wavelength may be EUV (extreme ultraviolet), E-Beam (electron beam) (par.0115).
With regard to claim 19, Kim et al. teach that a cross-lining reaction between organometallic compounds occurs in the exposed areas (par.0117).
With regard to claim 20, Kim et al. teach that the photoresist layer (106) comprises exposed region (106a) and non-exposure region (106b) (par.0117-0119).The non-exposure region (106b) of the photoresist layer is dissolved and removed using the developing solution (fig.4, par.0119).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure:
Jeon et al. (US 2026/0118751) teach an organometallic compound of formula:
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(par.0150).
Jeon et al. is not available as prior art.
Kobayashi et al. (US 2024/0116958) teach a compound of formula:
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(par.0026), wherein Q may be a substituted or unsubstituted aryl group with 6 to 30 carbon atoms (par.0020), and W may be represented by the formulas:
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(par.0022).
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/ANCA EOFF/Primary Examiner, Art Unit 1722
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