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 01/13/2023 and 09/20/2024 are being considered by the examiner.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1, 10, 17-18, 20, 25, 26, and 36 is/are rejected under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Pokora et al (US 4647952 B2, granted 03/03/1987).
Regarding Claims 1, 10, and 17-18, , Pokora discloses a formaldehyde-free resin conforming to the general formula (1):
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Where:
n is an integer greater than or equal to 2
Subunits are bonded through positions ortho- or -para to the hydroxyl group
Y is meta- or para- to the hydroxy group
Y is alkyl, halogen, aryl, phenylalkyl, allyl, carboxylic acid ester or acid,
Z is H, alkyl, halogen, aryl, phenyl alkyl, or a carboxylic acid ester or acid
Z may be bonded with the adjacent meta position to form a condensed benzene ring
Phenols used in preparing the resin conform to subunit (III) as described at Column 4 Lines 5-30, such as 4-aminosalicylic acid, 3-ethylphenol, and p-phenylphenol.
The resins are prepared by a free radical addition polymerization using a peroxide-peroxidase system, wherein the system facilitates the oxidation of the phenol.
Resins may be between 500 and 5,000 in molecular weight as a result of the polymerization.
Example 1 comprises a reaction system using potassium phosphate buffer, horseradish peroxidase, hydrogen peroxide, ethanol as a solvent, and a p-phenylphenol monomer. After reaction, the product was obtained by filtration.
Examples 2-9 maintain the same reaction solvent, oxidant system, and buffer, but use differing monomers:
Across the examples, the following relevant monomers are used:
P-phenylphenol
4-aminosalicylic acid
Bisphenol A
4-t-butylphenol
These monomers meet the limitations of the claim for where the polyphenolic resin has repeating units derived from at least one monomer selected from the group consisting of aromatic hydroxy compounds represented by the formulas (1A) and (1B) – specifically for where the aromatic hydroxy compound(s) meet the limitations of formula (1B) where:
Subscript m is 1, R2 is one of
Phenyl (C6 aryl group), as per p-phenylphenol
An isopropyl group (C3 alkyl) having a phenol substituent thereon, as per Bisphenol A
A t-butyl group (C4 alkyl), as per 4-tbutylphenol
Subscript m is 2
One of R2 is an amino group, the other R2 is a carboxylic acid group, as per 4-aminosalicylic acid
Example 7/8 features a copolymer made from 4-t-butylphenol and p-phenylphenol, Example 9 features a copolymer made from bisphenol A and p-phenylphenol (claim 12). Both of these examples use the same oxidizing agent as Example 1 (Claim 23).
As these monomers are polymerized in solution, while in solution the resultant polymer is part of a composition comprising a solvent (claim 17 and claim 18).
Regarding Claim 20, the reference makes no mention of the presence of metal impurities - and concerning the instant specification, none of Cu, Mn, Fe, Co, Ru, Cr, Ni, Sn, Pb, Ag, and/or Pd are present in the reference’s reagents. It can be inferred that the reference does not teach/disclose the presence of metal impurities in the composition(s) – and inferred that there are no metal impurities.
Regarding Claims 25, 26, 31, and 36, the preambles of these claims are being interpreted as “intended use”, as there are no further limitations that delimit film formation or resist compositions or optical members in a manner distinct from the polycyclic aromatic resin composition of claim 1, which is anticipated as discussed above.
The only practicable/definite limitation of claim 25 is the polycyclic phenolic resin according to claim 1. The resin of claim 1 is anticipated by the art and as such inherently must function as a composition for film formation.
Claim 26 recites the composition of claim 25 as the only definite/practicable limitation. The composition of claim 25 has been anticipated by nature of being the resin of claim 1, which is likewise anticipated as discussed above.
Claim 31 recites a composition for underlayer film formation for lithography comprising the composition of claim 25. The composition of claim 25 has been anticipated by nature of being the resin of claim 1, which is likewise anticipated as discussed above.
Claim 36 recites a composition for optical member formation comprising the composition for film formation according to claim 26, which correspondingly recites the composition for film formation of claim 25, which correspondingly recites the resin of claim 1. As for claims
Regarding claim 27, the limitations of the claim are met above as discussed regarding claims 1,25, and 26, where the composition comprises a solvent when it is synthesized as per the synthetic examples.
Claim(s) 1, 9, 13-14, and 17-18 is/are rejected under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Nonaka et al (US 2014033692 A1).
Regarding Claim 1, 9, 13-14, 17-18, 20, 25-27, 21-33, and 36, Nonaka discloses a resist underlayer film used in a lithography process, a process for applying the film as a composition, and a process for heat-treating the film (Abstract).
The resist underlayer film of Nonaka is generally described from [0052]-[0100], wherein the film is formed by applying a composition for forming to a substrate, then heat-treating the composition under an oxidative atmosphere at a temperature range of 150 to 600 degrees Celsius, wherein this heating results in a crosslinking reaction by oxidative coupling ([0055]-[0056]).
Synthetic Examples 1 and 2 disclosed at Tables 1 and 2 detail the compositions and resultant polymeric structures resulting from the application of a compound 1 with a compound 2, wherein the compound 2 is formaldehyde (formalin) used to facilitate a crosslinking reaction (claim 9) (Applicant’s own Specification discloses this use of aldehydes in this context – at [0163-[0165]). Synthetic example 2 features 200g of fluorenebisphenol, 75g of 37% formalin solution, and 5g of oxalic acid catalyst to be reacted at 100 degrees Celsius for 24 hours. After completion, the product was dissolved in methyl isobutyl ketone and the oxalic acid catalyst and metal impurities were removed with water. After processing, the resultant polymer was obtained having a molecular weight of 6,500 (claim 13) and a dispersity of 5.20.
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The above fluorene derivative in example 2 meets the limitations of the claim as Resin (1A) where:
R1 is a fluorene group (2-valent group having 13 carbons)
Subscript n is 1
Subscript m is 0
The resultant polymer embodiment from this reaction is presented in Table 2, which is not replicated here for brevity.
The polymer was dissolved in propylene glycol monomethyl ether acetate and filtered to prepare a solution for forming a resist underlayer film ([0135]) (claims 17 and 18). 10 parts by mass were dissolved in 100 parts of PGMEA – a solubility of 10% by mass (claim 14).
Regarding Claim 20, the reference claims that metal impurities are removed during the purification of the polymer and does not mention further impurities in the composition – the reference seems to indicate that there are 0 (0ppb) metal impurities.
Regarding Claims 25, 26, 31, and 36, the preambles of these claims are being interpreted as “intended use”, as there are no further limitations that delimit film formation or resist compositions or optical members in a manner distinct from the polycyclic aromatic resin composition of claim 1, which is anticipated as discussed above.
The only practicable/definite limitation of claim 25 is the polycyclic phenolic resin according to claim 1. The resin of claim 1 is anticipated by the art and as such inherently must function as a composition for film formation.
Claim 26 recites the composition of claim 25 as the only definite/practicable limitation. The composition of claim 25 has been anticipated by nature of being the resin of claim 1, which is likewise anticipated as discussed above.
Claim 31 recites a composition for underlayer film formation for lithography comprising the composition of claim 25. The composition of claim 25 has been anticipated by nature of being the resin of claim 1, which is likewise anticipated as discussed above – though the reference in this instance Also is directed to a resist underlayer film composition.
Claim 36 recites a composition for optical member formation comprising the composition for film formation according to claim 26, which correspondingly recites the composition for film formation of claim 25, which correspondingly recites the resin of claim 1. As for claims
Regarding claim 27 and 32, the limitations of the claim are met above as discussed regarding claims 1,25, and 26, and separately 1, 25, and 31, where the composition comprises a solvent when it is dissolved in PGMEA.
Regarding Claim 33, the composition of Example 2 discussed above regarding claims 1, 25, and 31 is applied to a silicon substrate and baked at 250 degrees under a 5% O2 nitrogenous atmosphere, then baked at 350 degrees Celsius to obtain a hardened film ([0136).
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) 34 and 35 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nonaka et al (US 2014033692 A1).
Regarding Claim 34 and 35, Nonaka disclsoses the limitations of the claim as discussed above regarding claim 1.
Nonaka however does not disclose a particular experimental embodiment wherein the composition is used to form a resist film on a substrate using the resist composition, exposed to radiation, and then developed.
This limitation is met by the general disclosure of the reference.
Nonaka discloses that the composition may comprise an acid generator at [0096], wherein the acid generator generates acid upon thermal decomposition of the component or by light irradiation.
The resist underlayer film is deposited onto a substrate, then a silicon-containing resist intermediate film is deposited thereatop, and a resist upper layer film is deposited atop the intermediate film. The resist upper layer film is patterned by mask-wise exposure to radiation having a wavelength of 300nm and then developed by alkali developing solution or organic solvent.
After development of the upper layer resist, the intermediate layer is etched such as with a fluorocarbon gas by using the upper layer pattern as a mask. After etching the intermediate layer, the resist underlayer film is etched using an oxygen or hydrogen gas using the intermediate film pattern as a mask. After etching the resist underlayer film, the substrate is etched using the resist underlayer film pattern as a mask ([0102]-[0117]).
Nonaka ascribes reduced unevenness to the underlayer film layer imparted by the composition and processing thereof, and that such reductions in unevenness results in a high precision pattern transfer into the substrate.
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 disclosure of Nonaka by using the resist underlayer film and trilayer patterning process taught to arrive at a processed substrate having a more precisely transferred pattern thereon.
Claim(s) 28-30 are rejected under 35 U.S.C. 103 as being unpatentable over Nonaka et al (US 2014033692 A1) as applied to claim 1 above, and further in view of Koes (US 5308744 B2) .
Regarding Claims 28-30, Nonaka disclsoses the limitations of the claim as discussed above regarding claim 1 and 25.
Nonaka disclsoses that the compositions may be 10 parts by mass solids dissolved in 100 parts by mass of PGMEA solvent – or, the solid may be present 9.1 parts by mass per 100 parts of total composition and the solvent be present in 90.9 parts per 100 parts of composition (Examples – [0136]).
Nonaka however does not disclose a particular experimental embodiment wherein the composition comprises a diazonaphthoquinone compound - Nonaka discloses that the composition may comprise an acid generator at [0096], wherein the acid generator generates acid upon thermal decomposition of the component or by light irradiation. The acid generator is not specifically named in the reference. Nonaka also does not specifically use the resist underlayer film composition as a photoresist layer though it is used in a photoresist patterning process as an underlying layer.
These limitations are met by Koes.
Koes teaches a photoacid generator having a structure delimited by Formula 1, wherein the compound is a diazonaphthoquinone derivative having a phenolic substituent. A preferred embodiment is made through the reaction of a 2,6-dimethylol-3,5-dinitro-p-alkyl phenol (Abstract)
Koes teaches a photosensitive composition comprising the diazonaphthoquinone derivative as a photoacid generator present in 5-40% by weight of the composition (Column 3 Lines 45-67). The composition may include vinyl polymers, or condensation polymers having acid labile groups as per Column 4 (The composition of Nonaka uses phenolic polymers made from condensation reactions), and organic solvents, wherein the composition may comprise solids in an amount ranging from 25 to 75% by weight.
The composition of Koes is coated onto a substrate to form a resist film, then exposed to radiation, and then developed to form a resist pattern as described in the examples of Columns 5-8
Koes ascribes improved performance to the photoacid generator used due to improved quantum yield in the irradiation step (Abstract).
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention from the disclosures Nonaka and the teachings of Koes by incorporating the diazonaphthoquinone photoacid generator into the composition of Nonaka and using the resultant composition in a photopatterning process to arrive at a patterned resist having improved patterning characteristics as imparted by the improved performance of the photoacid generator.
Claim(s) 10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nonaka et al (US 20140335692 A1) as applied to claim 1 above, and further in view of Ito et al (US 20090081376 A1).
Regarding Claim 10, Nonaka disclsoses the limitations of the claims as set forth above regarding claim 1.
Nonaka however does not disclose an experimental embodiment wherein a subunit having an ether bond formed by condensation of a phenolic hydroxy group is present.
This limitation is met by Ito.
Ito teaches a prepolymer that is excellent in heat resistance and can form a cured product having improved oil and water repellence (Abstract) for use in a photosensitive composition ([0001]), wherein the prepolymer is produced from the reaction of compounds having aromatic rings having halogens that are reactive to phenol groups with a phenolic compound in the presence of a hydrogen fluoride scavenger (such as a base), where an ether bond is formed as per reaction scheme (2) at [0062].
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 incorporating fluorinated aromatic compounds as per Ito into the reaction synthesis of Nonaka so as to arrive at polymeric embodiments having increased thermal resistance for use in the resist underlayer film.
Conclusion
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/A.P.T./Examiner, Art Unit 1737
/SALLY A MERKLING/SPE, Art Unit 1738
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