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
The disclosure is objected to because of the following informalities: Paragraph 0171 of the instant application’s specification provides a comparative example including a reaction scheme. The shown reaction scheme combines monobutyltin trichloride with 3 equivalents of acetic acid using NaOH to obtain the product according to Formula 15. However, the text underneath the specification recites that acrylic acid is used to produce the compound according to Formula 15. It is unclear if the reaction scheme is incorrect for showing acetic acid, or if the text is incorrect for stating acrylic acid.
Appropriate correction is required.
Regarding the specification, the Examiner notes that Synthesis Examples 1, 2, and 4 (refer to paragraphs 0158-0164 and 0168-0170 of the instant application’s specification) seemingly are intended to embody organotin compounds according to Formulas 3, 6, and 4, respectively, as recited by instant claims 6, 8, and/or 20. However, as written, claims 6 and/or 20 require that the aromatic heterocyclic rings of Formulas 3 and 4 have Ra4 or Ra7 be a (optionally substituted) C1 to C30 hydrocarbon group and claims 8 and/or 20 require that in Formula 6, Rb3 be a (optionally substituted) C1 to C30 hydrocarbon group. Whilst the specification as a whole provides support for the structures of claims 6, 8, and/or 20 (and thus, there is not an issue under 35 U.S.C. 112(a) or 112(b)), the Examiner notes that the compounds of Synthesis Examples 1, 2, and 4 do not represent inventive examples that provide support for Formulas 3, 6, and 4 as recited by instant claims 6, 8, and/or 20 as currently presented to the Examiner. It is unclear if this is the intent of the Applicant, which is why the Examiner makes note of this discrepancy.
Claim Rejections - 35 USC § 102
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-2, 9-10, 12-13, and 18-20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by KR 20210044591 A (hereby referred to as KR ‘591).
Regarding Claims 1-2, 9-10 12-13 and 18-20, KR ‘591 discloses a semiconductor resist composition and methods of forming patterns using the same. The resist composition comprises an organometallic compound represented by chemical formula 1 and a solvent (KR ‘591, paragraph 0010 of the English translation). The structure of chemical formula 1 is shown on page 6 of KR ‘591 and is reproduced below.
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In chemical formula 1, R1 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof (KR ‘591, paragraph 0014 of the English translation). X1 to X3 each independently represent a single bond, a hydrocarbon group, or an aromatic group (KR ‘591, paragraph 0015 of the English translation). Y1 is nitrogen (N), CH, COH, or CORb, wherein Rb is a hydrocarbon group or an aromatic group (KR ‘591, paragraph 0016-0018 of the English translation). KR ‘591 teaches several inventive examples showing specific organometallic compounds according to chemical formula 1 and their synthesis steps (KR ‘591, paragraph 0118-0136 of the English translation; refer also to pages 14-15 of the original KR ‘591 document). In particular, Synthesis Example 4, which yields the compound represented by Chemical Formula 5 (shown on page 15 of KR ‘591 and reproduced below), is of note.
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Chemical Formula 5 is an organometallic compound according to Formula 9 (as recited by instant claims 10 and 20), wherein Rc2 is an isopropyl group. Chemical Formula 5 represents an organometallic compound represented by Formula 1 (as recited by instant claims 1, 13, and 18), wherein M is tin (Sn), L1 is the ligand represented by Formula 8 (as recited by instant claims 9 and 19), R1 is an isopropyl group, the values of a and c are both zero, and the value of b is 1. KR ‘591 discloses that the compound according to Chemical Formula 5 is dissolved in a solvent to prepare a composition for a semiconductor photoresist (KR ‘591, paragraph 0145 of the English translation). The Examiner notes that in Chemical Formula 5, the value of a+b+c is 1 and the value of b+c is 1. Therefore, Chemical Formula 5 also anticipates instant claim 12.
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.
Claim(s) 3-8 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over KR 20210044591 A (hereby referred to as KR ‘591) in view of US 20210109442 A1 (hereby referred to as Moon) and US 20160222172 A1 (hereby referred to as Sotzing).
Regarding Claims 3-8 and 11, KR ‘591 discloses a photoresist composition comprising an organotin compound according to instant claim 1, as discussed above. However, KR ‘591 is silent in regards to a tridentate or tetradentate ligand according to instant claims 3-8 or an organometallic compound according to instant claim 11.
Moon teaches semiconductor photoresist compositions and methods of using the same. The semiconductor photoresist composition includes an organometallic compound including at least one selected from compounds represented by Chemical Formulae 1 to 3 and a solvent (Moon, paragraph 0059). Notably, Chemical Formula 1, which is reproduced below, is of a similar structure to the organometallic compounds represented by Formulae 3 and 6, as recited by instant claims 6 and 8.
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In Chemical Formula 1, R1 represents an optionally substituted C1 to C20 alkyl group, an optionally substituted C3 to C20 cycloalkyl group, and/or an optionally substituted C6 to C20 aryl group (Moon, paragraph 0061). X1 represents a substituted hydrocarbon group such as an ether or ester group (Moon, paragraph 0062-0063). Y1 represents an optionally substituted C1 to C20 aliphatic hydrocarbon group, an optionally substituted C3 to C20 alicyclic hydrocarbon group, and/or an optionally substituted C6 to C20 aromatic hydrocarbon group (Moon, paragraph 0064). The examples of Moon elucidate that the compound is synthesized from the reaction of an organotin precursor with a dicarboxylic acid (Moon, paragraph 0124-0125), wherein the structure of the acid determines the Y1 group. Thus, the broader disclosure of Moon teaches that the Y1 group may be a substituted aryl group or substituted alkyl group and resulting Y1 group is determined by the dicarboxylic acid compound utilized. Therefore, a structure represented by Formula 3 (according to instant claim 6) or Formula 6 (according to instant claim 8) may be obtained by appropriately selecting a dicarboxylic acid having a nitrogen atom between the two carboxylic acid groups. However, Moon’s compounds lack a third bonding site between the ligand that is analogous to L1 and the tin (Sn) atom.
Sotzing discloses organotin ester polymer compositions, methods of manufacture, and uses thereof. Particularly, paragraph 0066 of Sotzing discloses a synthesis method wherein 2,6-pyridinedicarboxylic acid (also known as dipicolinic acid) is dissolved in an aqueous solution of NaOH and reacted with dimethyltin dichloride dissolved in an organic solvent. This matches, for example, the synthetic route of Example 1 of the instant application (refer to paragraph 0158-0160 of the instant application’s specification), differing only in that Sotzing uses dimethyltin dichloride rather than dibutyltin dichloride. However, Sotzing discloses that the resulting product obtained is a polymeric material (Sotzning, paragraph 0066), whereas the instant application discloses a compound according to Formula 11. It is not clear to the Examiner why similar or identical reactants in similar reaction conditions yields two different types of products (compound instead of polymer). Nonetheless, Sotzing’s example from paragraph 0066 discloses a very similar synthetic route using similar or identical reactants as those disclosed by the Applicant and thus is deemed to render obvious the organometallic compound according to instant claims 3-6. The broader disclosure of Stozing further teaches the synthetic route involves reaction of an organic dicarboxy compound, such as a dicarboxylic acid, with a diorganotin dihalide (Stonzing, paragraph 0027). Suitable diorganotin dihalides include, for example, dimethyltin dichloride, dibutyltin dichloride, dioctyltin dichloride, and the like (Stonzing, paragraph 0029). The organic dicarboxyl compound is described as dicarboxylic acids and reactive derivatives thereof, such as acyl halides and esters (Stonzing, paragraph 0028). It is apparent from the broader disclosure of Stonzing that the choice of dicarboxylic acid (or derivative thereof) determines the A group as shown in formula (I) of Stonzing (Stonzing, paragraph 0019 and 0021). Thus, it would have been obvious to one having ordinary skill in the art prior to the effective filing date of the instant application to obtain an organometallic compound represented by Formula 6 of the instant application (refer to instant claim 8) by appropriately choosing an appropriate dicarboxylic acid species. For instance, the replacement of 2,6-pyridinedicarboxylic acid in the example disclosed in paragraph 0066 of Stonzing with a dicarboxylic acid such as iminodiacetic acid would yield the organotin compound according to Formula 6, as recited by instant claim 8. One having ordinary skill in the art would be motivated to make this substitution because Stonzing discloses that the A group may be a substituted hydrocarbylene or a heteroaryl (Stonzing, paragraph 0021), and thus the substitution would be prima facie obvious per MPEP 2143 I. E. Said substitution would yield an organometallic compound according to instant claims 7 and 8.
KR ‘591, Moon, and Sotzing are analogous art because each reference pertains to the synthesis of organotin compounds and their uses, including the use of said organotin compounds in resist compositions. It would have been obvious to one having ordinary skill in the art before the filing date of the instant application to replace the organotin compound disclosed by KR ‘591 with an organotin compound according to Formulas 3 and/or 6 of the instant application, as taught and/or suggested by the disclosures of Moon and Sotzing, because Moon teaches that the organometallic compound may exhibit less moisture penetration and thus has excellent storage stability (Moon, paragraph 0067) and because Sotzing teaches that the resulting polymer formed from the organotin compound exhibits high dielectric constant and low conductivity (Sotzing, paragraph 0018).
Claim(s) 14-17 are rejected under 35 U.S.C. 103 as being unpatentable over KR 20210044591 A (hereby referred to as KR ‘591).
Regarding Claims 14-17, KR ‘591 discloses a photoresist composition according to instant claim 13, wherein the photoresist composition comprises an organotin compound and a solvent, as discussed above. Furthermore, the organotin compound taught by KR ‘591 (for instance, Chemical Formula 5 as shown on page 15 of KR ‘591), is an organotin compound represented by Formula 9 of the instant application (refer to instant claims 10 and 20). However, KR ‘591 is silent in regards to the energy levels of the organotin compound in the various states of bonding with a water molecule, as recited by instant claims 14-17.
However, the organotin compound according to Chemical Formula 5 disclosed by KR ‘591 is a chemical analogue to the organometallic compound A-3 shown by the instant application’s specification (refer to paragraphs 0165-0167 of the instant application’s specification). The difference between Chemical Formula 5 of KR ‘591 and organometallic compound A-3 is the hydrocarbon group bonded to the tin atom (isopropyl for Chemical Formula 5, n-butyl for compound A-3). The instant application further suggests that when L1 of the organometallic compound is a tridentate or tetradentate ligand, the reactivity of the compound with water is reduced (refer to paragraph 0044-0051 of the instant application’s specification), and in particular, compound A-3 demonstrates a first reaction energy that satisfies instant claim 14 (refer to paragraphs 0184-0185 of the instant application’s specification). MPEP 2144.09 states that a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. In this case, the Chemical Formula 5 organotin compound disclosed by KR ‘591 is structurally similar to compound A-3 of the instant application, and KR ‘591 discloses the use of the organotin compound represented by Chemical Formula 5 in a photoresist composition, indicating similar utility. As compound A-3 of the instant application has been described by the Applicant as satisfying the respective energies associated with the various states when the organometallic compound is bonded to a water molecule (refer to paragraphs 0044-0051 and 0184-0185 of the instant application’s specification), it would be expected by one having ordinary skill in the art that the organotin compound represented by Chemical Formula 5, as disclosed by KR ‘591, possesses similar energy levels to compound A-3 (absent of evidence to the contrary), due to the close structural similarities of the two chemical structures. Refer to MPEP 2144.09. Furthermore, the broader disclosure of KR ‘591 discloses that in chemical formula 1 (the generalized structure of the organotin compound disclosed by KR ‘591), R1 may be a substituted or unsubstituted C1 to C20 alkyl group (KR ‘591, paragraph 0058 of the English translation). Thus, it would have been obvious to one having ordinary skill in the art before the filing date of the instant application to replace the isopropyl group in Chemical Formula 5 with a butyl group, per the teachings of KR ‘591, to obtain an organotin compound equivalent to organometallic compound A-3 of the instant application’s specification. Refer to MPEP 2143 I. E. Therefore, claims 14-17 of the instant application are rendered prima facie obvious in view of the disclosure of KR ‘591.
Conclusion
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/JAYSON D COSGROVE/Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734
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