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 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 1 (and all dependent claims 2-5, 11, 21, 23 and 26) and 25 (and dependent claim 28) are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as failing to set forth 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.
Regarding claims 1 and 25, the claimed requirements are unclear, since the limitations of B content of 10 at% to 35 at% and O content of 10 to 70 at% cannot be satisfied when the substituent R has higher number of atoms such as a C30 alkyl group. A C30 alkyl group in Formula 1, would result in 2.4 at% B and 3.5 at% O, which are outside the claimed ranges. Thus, applicant is encouraged to revise the substituents R such that they simultaneously satisfy the requirements at % of both boron or oxygen or change the at% of B and O.
Additionally, it is noted that applicant’s own inventive examples 5 and 7 (specification Table 1) fail to satisfy the B at% requirements. Therefore, it remains unclear if the limitation of B at% is an inventive feature of the invention.
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)(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.
Claims 1-3, 5, 11 and 26 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ishibe JP 2016018133.
Regarding claims 1 and 3, Ishibe teaches (para [0114]) a compound(2,4,6-triphenyl boroxin) represented by the following formula as shown below, which reads on Formula 1, with a =3.
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Resulting in boron content of 10.6 at%, and oxygen content 15.4 at%, which meets the claimed requirement.
The claimed preamble “hardmask-forming” which merely states the purpose or intended use of the compound of Formula 1, rather than provide any distinct definition of any of the claimed invention’s limitations, is not considered a limitation, See MPEP 2111.02 II.
Since the structure of the Ishibe’s boron compound meets the claimed requirement of Formula 1, it meets the requirement of hardmask-forming compound.
Regarding claim 2, Ishibe teaches (para [0114]) a hardmasking-forming compound(2,4,6-trioxy boroxin) represented by the following formula as shown below, which reads on Formula 1, with a =3.
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Resulting in boron content of 19 at%, and oxygen content 55 at%, which meets the claimed requirement.
Regarding claim 5, Ishibe teaches (para [0150]) 9-phenanthrene boronic acid, meeting the claimed requirement of fused polycyclic group substituent.
Regarding claim 11, Ishibe teaches (para [0147]) dissolving the boron compound in a solvent, meeting the claimed requirement.
Regarding claim 26, the required B-O network structure in the cured film (or layer) (para [0130]) of Ishibe which comprises the boron compound (para [0150], C-6 phenyl boronic acid), will be inherently generated by Ishibe’s boron compound phenyl boronic acid, which is identical to the applicant’s reactant (Formula 4, Synthesis Example 1). Applicant’s attention is directed to: Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
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.
Claim(s) 6-8, 10, 12, 21-22, 25 and 27-28 under 35 U.S.C. 103 as being unpatentable over Ishibe JP 2016018133, as applied to claims 1-3, 5, 11, 26 above.
Regarding claims 6, 7 and 22, Ishibe teaches a composition (overview, claim 2, para [0103]) comprising a boron compound of formula (2) as shown below.
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Ishibe notes that m can be 2 to 10 and that the substituents R3 may be different and which can be selected from alkyl groups having 1 to 20 carbon atoms or alkoxy groups having 1 to 20 carbon atoms.
Based on the teachings of Ishibe, it would have been obvious to one of ordinary skilled in the art before the effective filing date of the invention to have a composition with formula 2 which complies with the claimed requirement where m equals 10 such that b1=b2=5, when equal mol fractions of different R3: such as CH3 alkyl and OCH3 alkoxy form the repeat units, leading to required R1 as -CH3 alkyl and R2 as -OCH3 alkoxy as depicted below, which also meets the claimed b1/(b1 +b2) =0.5.
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The at% of B in the above structure is total atomic mass of B atoms/total atomic mass of all atoms = 110/500 = 22 at% B, similarly at % of O is = 240/500 =48 at%.
The claimed preamble “hardmask-forming” which merely states the purpose or intended use of the compound of Formula 2, rather than provide any distinct definition of any of the claimed invention’s limitations, is not considered a limitation, See MPEP 2111.02 II.
Since the obvious structure as shown above of the Ishibe’s boron compound (2) meets the claimed requirement of Formula 2, it meets the requirement of hardmask-forming compound.
Regarding claims 6 (this is an alternate rejection of claim 6) and 8, Ishibe teaches (overview, claim 2, para [0103]) boron compound (C) with formula (1) as depicted below.
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Where exemplified compound of Formula (1) are 2-methylpropyl boronic acid and phenyl boronic acid (para [0110]). Based on the teachings of Ishibe, it would have been obvious to one of ordinary skilled in the art before the effective filing date of the invention to create a composition where both the 2-methylpropyl boronic acid and phenyl boronic acid are present as reactants. Since these boron compound reactants are identical to the applicant’s reactants (instant specification Formula 3 and Formula 4 in synthesis example 1) the required polymer repeat units and structures would necessarily follow. Applicant’s attention is brought to "It is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose.... [T]he idea of combining them flows logically from their having been individually taught in the prior art." In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072.
Regarding claim 10, Ishibe teaches naphthyl boronic acid (para [0110]), thus making the claimed requirement obvious.
Regarding claim 12, Ishibe teaches (para [0147]) dissolving the boron compound in a solvent.
Regarding claim 21, Ishibe teaches (paras [0102] and [0103]) a composition comprising a boron compound of formula (2) as shown below.
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Where the substituent R3 may be -OCH3, and m can be 2 to 10, which overlaps with the claimed requirement.
Regarding claim 27, as discussed in the alternate rejection of claim 6, Ishibe teaches exemplified compounds of Formula (1) are 2-methylpropyl boronic acid and phenyl boronic acid (para [0110]). The required B-O network structure in the cured film (para [0130]) of Ishibe would be generated by Ishibe’s reactant compounds 2-methylpropyl boronic acid and phenyl boronic acid, which are identical to the applicant’s reactants (Formula 3 and Formula 4, Synthesis Example 1). Applicant’s attention is directed to: Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
Regarding claims 25 and 28, Ishibe teaches (overview, claim 2, paras [0102] and [0103]) a composition comprising a boron compound of formula (2) as shown below.
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Ishibe notes that m can be 2 to 10, which overlaps with applicant’s a, and that the substituent R3 may be an alkoxy groups having 1 carbon atom, which satisfies the boron and oxygen at% content.
Ishibe discloses the preparation of a radiation sensitive composition (overview), corresponding to applicant’s hardmask composition comprising the boron compound which is dissolved in a solvent where the solvent content is 50 to 95% by mass (para [0128]), thus implying that the solid content of the composition is 5% to 50 % by mass, which overlaps the claimed requirement.
Since the structure of the Ishibe’s boron compound meets the claimed requirement of Formula 1, it meets the requirement of hardmask-forming compound and would also generate the required B-O network structure in a cured film (corresponding to hardmask layer) derived from the overall composition (Ishibe, overview).
Claim(s) 4 and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Ishibe as applied to claims 1-3, 5, 11, 26 and claims 6-8, 10, 12, 21-22, 25 and 27-28, above, and further in view of Stoessel et al. US 2009/0134384 A1.
Regarding claims 4 and 9, as discussed when addressing claims 1 and 6 (alternate rejection) Ishibe teaches the utilization of phenyl boronic acid (and 2,4,6-triphenyl boroxin). Ishibe does not address cyclopentadiene based substituent on the boron compound, however analogous reference Stoessel who teaches overlapping boron compounds (paras [0019] and [0057]) considers C5 and C6 aromatic substituents to be equivalents (para [0051]).
Based on the teachings of Ishibe and Stoessel, it would have been obvious to one of ordinary skilled in the art before the effective filing date of the invention to have created a boron compound where the phenyl ring is substituted with cyclopentadiene, since it is prima facie obvious to substitute art recognized equivalents for the same purpose. See MPEP 2144.06 II.
Claim(s) 23 and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Ishibe as applied to claims 1-3, 5, 11, 26 and claims 6-8, 10, 12, 21-22, 25 and 27-28, above, and further in view of Niebylski US4,873,353.
Regarding claims 23 and 24, Ishibe fails to mention specific permutation of the suitable solvent, one of ordinary skill would take guidance from related disclosures to ascertain what might be used in that capacity. Analogous reference Niebylski who also teaches similar boron based structures (col 1, lines 46-68) recommends solvent 1-methyl-2-pyrrolidone for the creation of a coating solution (col 2, line 16 and line 26).
It would have been obvious to one of ordinary skilled in the art before the effective filing date of the invention to have utilized solvent 1-methyl-2-pyrrolidone for dissolving Stoessel’s boronic acid anhydrides derivatives as taught by Niebylski for the same application of creating a coating solution.
Response to Arguments
Applicant's arguments filed 05/18/2026 have been fully considered, please see the responses below.
Applicant discusses (pages 3-5, III. A and B) that the present claims are directed to hardmask-forming compounds (and compositions) including either a moiety represented by Formula 1 or Formula 2 and that Ishibe does not anticipate the present claims, since it does not teach a “hardmask-forming compound”, but provides a radiation-sensitive resin composition that can be used for the formation of a cured film. Applicant submits that Ishibe’s Formula 1 does not teach either present Formula 1 or
Formula 2 of the present claims.
In response, while it is acknowledged that Ishibe does not highlight the use of the boron compounds as hardmark forming compounds, since Ishibe’s boron compounds meet the structural requirements of Formula 1 and Formula 2 (as discussed in the rejection above), they would be inherently suitable as hardmark-forming compounds. Applicant is reminded that: "where a patentee defines a structurally complete invention in the claim body and uses the preamble only to state a purpose or intended use for the invention, the preamble is not a claim limitation"); Kropa v. Robie, 187 F.2d at 152, 88 USPQ2d at 480-81 (preamble is not a limitation where claim is directed to a product and the preamble merely recites a property inherent in an old product defined by the remainder of the claim); STX LLC. v. Brine, 211 F.3d 588, 591, 54 USPQ2d 1347, 1350 (Fed. Cir. 2000), see MPEP 2112.02 II.
With respect to applicant’s argument that Ishibe’s Formula (1) shown below does not teach the required Formula 1 or Formula 2.
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Ishibe’s Formula (1) with n=1, R1 as hydrogen and R2 as alkyl, alkoxy, and aryl groups meets the claimed Formula 1, where a=1. Additionally, applicant’s own examples (synthesis examples 1 and 2, which include Formulae 3-6) show structures which are consistent with Ishibe’s Formula (1). Therefore, applicant’s arguments against Ishibe not anticipating any of the claims is not convincing. The amended claims 1-3, 5, 11 and 26 are anticipated by Ishibe.
Applicant adds (page 5, 3.) that Ishibe’s Formula (2) because of broad disclosure of R3 does not anticipate the present claims including Formula 1. As discussed in the main rejection Ishibe’s disclosure of compound (2,4,6-triphenyl boroxin) which complies with Ishibe’s Formula (2), meets all the amended claimed requirements of claim 1. Applicant’s attention is directed to: "A generic claim cannot be allowed to an applicant if the prior art discloses a species falling within the claimed genus." The species in that case will anticipate the genus. In re Slayter, 276 F.2d 408, 411, 125 USPQ 345, 347 (CCPA 1960); In the instant case the species (2,4,6-triphenyl boroxin) anticipates the amended claim 1.
With respect to applicant’s argument (page 6, 4.) that Ishibe does not anticipate Formula 2, since there is no indication in Ishibe that there should be specifically different R3 groups that are each part of a repeating unit.
While it is recognized that Ishibe’s provides various possible R3, however all the R3 disclosed meet the requirements of R1 and R2 of applicant’s Formula 2. Ishibe provides a clear guidance that R3 can be different and that the total repeat units can be 10, one of ordinary skill in the art would at once envisage the specific compound (as discussed in the main rejection) within the generic chemical Formula (2) of Ishibe, which meets the claimed Formula 2. Ishibe’s disclosure renders the amended claim 6 requirements obvious.
Applicant notes (page 6, C. and page 7) that the present claims 1 and 25 are not obvious over Ishibe, since Ishibe does not teach the required content of boron or oxygen, and that one would not pick and choose any particular compound of Ishibe to achieve the recited boron and oxygen. In response, reference Ishibe teaches 2,4,6-trimethoxyboroxin and 2,4,6-triphenyl boroxin (para [0150]), which satisfy the boron and oxygen content, as preferred boron compounds for compositions used for formation of cured films in the inventive examples (Table 1, para [0151]). Ishibe continues to anticipate the requirements of claim 1. The requirements of claim 25 are obvious over the disclosure of Ishibe.
Applicant submits (page 8, 2.) that claims that include Formula 2 are not obvious over Ishibe, since there is no guidance in Ishibe to lead to two repeating units to meet the b1/(b1+b2) range. As discussed in the main rejection the required Formula 2 would be readily envisaged by one of ordinary skilled in the art, given the overlapping repeat units of Ishibe’s Formula (2) and R3 units which meet the requirements of R1 and R2. Since Ishibe notes that R3 can be different, equal mole fractions of two different R3 groups would result in the required range of b1/(b1+b2) range as discussed in the main rejection.
Applicant notes (page 8, 3.) the distinction of the required solvents of claims 23 and 24 over Ishibe. While Ishibe does not provide the specific solvents, the required solvents are made obvious over Ishibe and Niebylski.
Applicant’s arguments (page 9, 4.) against Ishibe in view of Moon are moot, since Moot is not relied for the rejection as presented above.
Applicant’s Examiner Interview summary conducted on April 24, 2026 is acknowledged (remarks page 1, I.), applicant notes that advantageous features are added to the amended claims which are not taught by Ishibe’s radiation sensitive compositions for display applications. In response it is noted that the additional features of boron and oxygen content do not provide a distinguishing feature over Ishibe. Ishibe teaches the required boron compounds and the compositions derived from them and therefore anticipates claim 1 and renders the claimed Formula 2 obvious.
Applicant’s arguments are found to be unconvicting and reference Ishibe continues to provide the support for maintaining the rejection.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Surbhi M Du whose telephone number is (571)272-9960. The examiner can normally be reached M-F 9:00 am to 5:00pm.
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/S.M.D./
Examiner
Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765
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