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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 01/16/2024, 11/08/2024, 04/09/2025, and 07/08/2025 are being considered by the examiner.
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) 1-16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Heo et al (KR 20160099997 A).
Regarding Claim 1, 5,7, 8 and 11-14 Heo teaches a polymer, organic film composition, and patterning process using such (Background Technique), wherein the polymer material may be used in a hardmask for use in lithographic processing.
Heo does not explicitly provide an experimental embodiment meeting the limitations of the claims.
These limitations are met by the general disclosure of the reference.
The polymer embodiment conforms to the general formula presented at [0013], wherein
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X1-X4 each may independently be a substituted or unsubstituted aromatic ring group
At least one of X1-X4 is a polycyclic aromatic ring group that may be substituted or unsubstituted.
* is a linking point
X1-X4 may each independently be chosen from Group 1
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The polymer may contain a plurality of moeities corresponding to formula 1, and may have different structures independently that still conform to formula 1 ([0059])
Preferably, at least one of the aromatic ring groups presented from X1-X4 bears a hydroxy group, wherein the number of hydroxy groups is not particularly limited.
Preferably, at least two of X1-X4 are a polycyclic group such as naphthalene or coronene ([0066])
Exemplary embodiments of the polymer may be those presented at [0067]-[0077] as chemical formulas 1-1 through 1-3.
The polymer of should bear a molecular weight ranging from 1,000 to 200,000 (claim 11), and is included in the composition in an amount ranging from 0.1wt% to 30wt% based on the total amount of the composition (claim 12) ([0081]).
In the experimental examples, a monomer conforming to chemical formula A is generated as described at [0103]-[0104].
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The compound above is used in a synthetic scheme where it is reacted with hydroxypyrene in the presence of p-toluenesulfonic acid and 1,4-dioxane as per [0114]-[0115].
The resultant polymer has the following structure 1aa
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The coronene structure meets the limitations of claim 1 for where claimed B is coronene (claim 5, where the coronene is unsubstituted), and the -C-(naphthalene)- linkages meet the limitations of the claim for where X1 and X2 are each naphthalene as claimed.
Claimed structure A is not present in the experimental result provided. However, the reference clearly teaches that X1 (corresponding to the reference’s experimentally embodied hydroxypyrene and claimed structure A) (claim 7, 8 where naphthalene is present in both the claimed groups) may be a substituted aryl group such as naphthalene, wherein the group may have any number of hydroxyl groups thereon. Chemical formula [1-2] further depicts a multi-hydroxy-substituted (d=0-4) naphthalene subunit in the position corresponding to the above hydroxypyrene - a person having ordinary skill in the art would have found it obvious to substitute a hydroxypyrene for a dihydroxy-substituted naphthalene as the reference establishes that these aryl groups and substituted variants thereof are equivalents to one another by nature of their presentation together. Such substitution would amount to the selection of a small number of embodiments that are taught by the reference to be roughly comparable in properties/performance and thus behave predictably when substituted for one another.
Further - Applicant’s own specification recites the same monomer of chemical formula a (Specification’s Compound A) in similar reaction conditions using heating, p-toluenesulfonic acid, and dioxane, except where 1,5-dihydroxynaphthalene is used in place of hydroxypyrene (Specification [00125]-[00127) - it is clear that the substitution is chemically feasible to produce a product.
The polymer is included in a composition comprising a surfactant, thermal acid generator, plasticizer, crosslinking agent, or other additive, as well as solvent ([0079]-[0086]). Suitable solvents include but are not limited to propylene glycol, propylene glycol diacetate, methoxy propanediol, N,N-dimethylformamide, N,N-dimethylacetamide, or another solvent described in [0080](claim 13).
The composition is used as a hardmask layer or other suitable layer as per [0087] – the composition may be used as a hardmask composition, wherein the material composition is coated onto a substrate and cured such as through a heat treatment (claim 14).
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date by the simple substitution of dihydroxynapthalene or another multi-substituted naphthalene into the synthetic procedure of the reference and from the generally disclosed embodiments of arylene moeities presented regarding chemical formula 1 from the reference with the expectation that the substitution of various arylene embodiments therein would result in a chemically similar product predictably capable of being used in a hardmask layer composition.
Regarding claims 2, 3 and 4, Heo teaches the limitations of the claim as discussed above regarding claim 1, where the embodiment generated when a di-hydroxy or multi-hydroxy-substituted naphthalene is present in the chemical formula 1 (and/or substituted for the hydroxypyrene in the chemical example of Heo) meets the limitations of the claim for where claimed R1 is a hydroxy group and subscript n is an integer of 2-4. This embodiment meets the limitations of claim 4 for chemical formula 2-1 where subscript n is 2-3.
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date by the simple substitution of dihydroxynapthalene or another multi-substituted naphthalene into the synthetic procedure of the reference and from the generally disclosed embodiments of arylene moeities presented regarding chemical formula 1 from the reference with the expectation that the substitution of various arylene embodiments therein would result in a chemically similar product predictably capable of being used in a hardmask layer composition.
Regarding Claim 6, Heo teaches the limitations of the claim as discussed above regarding claim 1.
However, Heo does not disclose an experimental embodiment wherein the coronene (corresponding to claimed structure B of claim 1) is substituted with a hydroxy, halogen, or other group as claimed.
This limitation is met by the general disclosure of the reference.
Heo teaches, as discussed above regarding claim 1, that the arylene groups X1-X4 may each independently be substituted. As such, the hydroxy-substitution of a coronene embodiment for use in a polymer as prompted by the art is within the scope of the disclosure – as is substitution with a halogen based on the disclosure at [0064].
Further, in the general formula [1-1] at [0068], a hydroxy-substituted coronene group is clearly depicted, where b=0-4 as stated at [0075].
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date by the simple substitution of a hydroxycoronene or halocoronene into the synthetic procedure of the reference and from the generally disclosed embodiments of arylene moeities presented regarding chemical formula 1 from the reference with the expectation that the substitution of various arylene embodiments therein would result in a chemically similar product predictably capable of being used in a hardmask layer composition.
Regarding Claim 9 and 10, Heo teaches the limitations of the claim as discussed above regarding claim 1,
However, Heo does not disclose an experimental embodiment wherein the polymer chain meets the structural limitations of the claims.
These limitations are met by the general disclosure of the reference.
Referring back to the rejection of claim 1, when dihydroxy naphthalene is used in the synthetic procedure described in [0113]-[0115] in place of the hydroxypyrene unit, the resultant structure meets the limitations of claim 1, and the formula unit would comprise the structures of claim 9’s Chemical Formula [1-2] where X12 and X22 are naphthalene, and claim 10’s Chemical Formula [1-8].
The reference clearly teaches that X1 (corresponding to the reference’s experimentally embodied hydroxypyrene and claimed structure A) may be a substituted aryl group such as naphthalene, wherein the group may have any number of hydroxyl groups thereon. Chemical formula [1-2] further depicts a multi-hydroxy-substituted (d=0-4) naphthalene subunit in the position corresponding to the above hydroxypyrene - a person having ordinary skill in the art would have found it obvious to substitute a hydroxypyrene for a dihydroxy-substituted naphthalene as the reference establishes that these aryl groups and substituted variants thereof are equivalents to one another by nature of their presentation together. Such substitution would amount to the selection of a small number of embodiments that are taught by the reference to be roughly comparable in properties/performance and thus behave predictably when substituted for one another.
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date by the simple substitution of dihydroxynapthalene or another multi-substituted naphthalene into the synthetic procedure of the reference and from the generally disclosed embodiments of arylene moeities presented regarding chemical formula 1 from the reference with the expectation that the substitution of various arylene embodiments therein would result in a chemically similar product predictably capable of being used in a hardmask layer composition.
Regarding Claim 15 and 16, Heo teaches the limitations of the claim as discussed above regarding claim 1.
However, Heo does not explicitly disclose an experimental example wherein a composition comprising an experimental example of the claimed polymer is used in a pattern forming method.
These limitations are met by the general disclosure of the reference.
Heo teaches a method of forming a pattern using the taught organic composition from [0089]-[0099], wherein a material layer is deposited onto a substrate, and then the taught organic composition is deposited onto a substrate and heated to form a hardmask layer, then a silicon containing thin film layer is formed atop the hardmask. After this, a photoresist layer is formed on the hardmask layer. The photoresist is exposed and developed to form a photoresist pattern. After, the silicon layer is selective removed, the hardmask layer is selectively removed using the silicon layer as a mask, and the material layer is exposed through the selectively removed hardmask layer. The material layer is then etched on the exposed part(s).
Heat treatment of the organic hardmask composition may take place at a temperature ranging from 100 to 500 degrees Celsius (claim 16 – [0093]) for 10 seconds to 1 hour.
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the filing date from the general disclosure of the reference by applying the taught method of Heo to the composition of Heo, using a known method to treat an art-taught composition in order to arrive at the predictable result of a lithographic patterned hardmask and associated products stemming from the processing thereof.
Conclusion
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/A.P.T./Examiner, Art Unit 1737
/SALLY A MERKLING/SPE, Art Unit 1738
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