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 .
Response to Amendment
Applicant’s Amendment filed 10/14/2025 has been entered and is being considered. Claims 1 and 18 are amended. Claim 9 is canceled. No new matter has been added with this amendment.
Response to Arguments
Applicant’s arguments, see remarks filed 10/14/2025, with respect to the 35 USC 102 and 103 rejections of claims 1-3, 8-14, 16, and 18 have been fully considered but is not persuasive. Applicant argues that the polymer of structure (II) in Wang does not satisfy the newly amended claim limitation of “said resin includes solely repeating units having a ring structure in a side chain”, citing the methacrylate ester monomer having an R3 side chain group. The Examiner disagrees with this argument since the R3 group off of the methacrylate ester further includes dicyclopentyl, adamantyl groups and other cyclic side groups (paragraph 15, page 3). See the detailed action below.
Examiner thanks Applicant for pointing out a typographical error that included the reference Mihara in the rejection of Claim 7, and Applicant is correct to assume the rejection of Claim 7 was based solely on Wang in view of Mihara.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1, 3-6, 8, 10-13, 16, 18 are rejected under 35 U.S.C. 103 as obvious over Wang (CN 105669889, reference citations from the English translation).
Regarding Claims 1, 3, and 16, Wang teaches styrene a copolymer of a photoacid-containing styrene derivative having the structural formula shown in Formula (I) (paragraph 11). The method of preparing the compound of Formula (I) involves first step comprising reacting a styrene sulfonate salt of sodium, ammonium, or potassium, p-acetoxystyrene and methacrylate or methacrylic acid to form the copolymer represented by Formula (II) (paragraph [16-17]) (Claim 16). The potassium and ammonium salts of styrene sulfonate satisfy the compound of formula (P-1) where R1 is H, L1 is a single bond, Arp1 is an aromatic ring, and M+ is potassium or ammonium cation and the formula (P-2) where M+ is potassium or ammonium cation (Claim 3). The p-acetyoxystyrene monomer satisfies the copolymerizable monomer of formula (A-1) where R2 is methyl, Ara1 aromatic ring, n is 1, Y is an acetoxy substituent wherein the acetoxy substituent is an acid-decomposable group. Additionally, Wang discloses in Example 3 the polymerization of styrene sulfonate sodium salt, acetoxy styrene, and dicyclopentyl methacrylate, all of which contain cyclic side groups (paragraph [75-77]).
The polymer of Example 3 comprises a sodium counterion, not a potassium or ammonium counterion.
However, Wang discloses styrene sulfonate salts may have the counterions sodium, ammonium, or potassium and are discussed as equivalents to one another. Thus, it would have been obvious for one of ordinary skill in the art to have substituted the sodium counterion of Example 3 with a potassium or ammonium counterion through routine experimentation. One of ordinary skill would reasonably expect such a modification to form a resist polymer with similar resist properties.
Regarding the lithium counterion, Wang is silent to the counterion of styrene sulfonate having a lithium counterion.
However, since Wang discloses both sodium and potassium ions as working counterions, it would have been obvious for one of ordinary skill in the art to envision similar counterions such as lithium. Sodium, potassium, and lithium are all group 1 elements on the periodic table, and one of ordinary skill would reasonably expect the substitution for one Group 1 cation for another to behave similarly. A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963). See MPEP 2144.09.
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Regarding Claims 4-6, Wang further discloses that in the terpolymerization step with styrene sulfonate salt, it is necessary to select a solvent having a relatively high polarity such as DMSO, methanol, or DMF (paragraph 22). While Wang explicitly uses DMSO in the polymerization step involving the styrene sulfonate salt (paragraph 49-50), other solvents disclosed having a high polarity are also suitable to perform the polymerization step. Based on the disclosure of Wang, the possible solvents envisioned include polar solvents such as methanol which is an alcohol. Nevertheless, it would further have been obvious for one of ordinary skill in the art to have selected the polymerization solvent to be methanol based on the disclosure of Wang. Wang discloses the polar solvents as equivalent solvents in the polymerization step involving the styrene sulfonate salt. One of ordinary skill would reasonably expect this modification to successfully polymerize the aforementioned monomers. This modification would make 100% of the solvent an alcohol-based solvent such as methanol.
Regarding Claim 8, the discussion of Claim 1 is relied upon as above. Wang further discloses the subsequent steps of deprotecting the acetoxy group into a phenolic hydroxyl group under acid catalyzed conditions to obtain polymer represented by general formula (III) and further subjecting the polymer represented by formula (III) to an ion exchange reaction with an onium salt compound to obtain the polymer derivative represented by formula (IV) (paragraph 17-20).
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Regarding Claim 10 and 11, the discussion of Claim 1 is relied upon as above. The acetoxystyrene monomer of Wang satisfies the formula where Y1 is represented by (AY-2) where Ra3 is an alkyl group. Furthermore, the acetoxystyrene monomer of Wang satisfies the formula (A-4) where Rb3 is an alkyl group.
Regarding Claim 12, the discussion of Claim 11 is relied upon as above. Wang further discloses the step involving deprotecting the acetoxystyrene-containing copolymer under acid catalyzed conditions to obtain a copolymer having the repeating unit represented by (AP-1) (paragraph 18).
Regarding Claim 13, the discussion of Claim 12 is relied upon as above. Wang further discloses the step involving reacting the partial phenolic hydroxyl in the formula (IV) with di-tert-butyl dicarbonate in the presence of an organic base to form a tert-butoxycarbonyl (t-BOC) group as shown in the general formula (I) (paragraph 20). This conversion from vinylphenol to t-BOC satisfies the repeating unit represented by Formula (AP-2) where Y2 is a group that leaves due to an action of an acid.
Regarding Claim 18, Wang teaches the method of preparing the compound of Formula (I) involves first step comprising reacting a styrene sulfonate salt of sodium, ammonium, or potassium, p-acetoxystyrene and methacrylate or methacrylic acid to form the copolymer represented by Formula (II) (paragraph [16-17]). The polymerized potassium and ammonium salts of styrene sulfonate satisfy the compound of formula (P-1) where R1 is H, L1 is a single bond, Arp1 is an aromatic ring, and M+ is potassium or ammonium cation and the acetoxystyrene satisfies Formula (A-2) where Rb3 is methyl. Additionally, Wang discloses in Example 3 the polymerization of styrene sulfonate sodium salt, acetoxy styrene, and dicyclopentyl methacrylate, all of which contain cyclic side groups (paragraph [75-77]).
The polymer of Example 3 comprises a sodium counterion, not a potassium or ammonium counterion.
However, Wang discloses styrene sulfonate salts may have the counterions sodium, ammonium, or potassium and are discussed as equivalents to one another. Thus, it would have been obvious for one of ordinary skill in the art to have substituted the sodium counterion of Example 3 with a potassium or ammonium counterion through routine experimentation. One of ordinary skill would reasonably expect such a modification to form a resist polymer with similar resist properties.
Regarding the lithium counterion, Wang is silent to the counterion of styrene sulfonate having a lithium counterion.
However, since Wang discloses both sodium and potassium ions as working counterions, it would have been obvious for one of ordinary skill in the art to envision similar counterions such as lithium. Sodium, potassium, and lithium are all group 1 elements on the periodic table, and one of ordinary skill would reasonably expect the substitution for one Group 1 cation for another to behave similarly. A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963). See MPEP 2144.09.
Claim 7 is rejected under 35 U.S.C. 103 as obvious over Wang (CN 105669889, reference citations from the English translation) as applied to Claim 1 in view of Mihara (US 20150152208).
Regarding Claim 7, the discussion of Claim 1 is relied upon as above. Wang is silent to passing the monomer through a filter.
However, Mihara discloses curable compositions that in order to prevent defects in recessed and raised portion of a cured product caused by particulate contaminants, after the components are mixed a curable composition may be passed through a filter having a pore size in the range of 0.001 to 5 micrometers (paragraph [0098]).
It would have been obvious for one of ordinary skill in the art to have modified the method of Wang to filter the monomers using a filter with a pore size in the range of 0.001 to 5 micrometers. One of ordinary skill would have been motivated to make this modification to prevent defects in recessed and raised portions as suggested by Mihara.
Claims 14 and 15 are rejected under 35 U.S.C. 103 as obvious over Wang (CN 105669889, reference citations from the English translation) as applied to Claims 11 and 13 in view of Malik (US Patent No. 6,159,653).
Regarding Claim 14 and 15, the discussion of Claims 11 and 13 are relied upon as above. Wang discloses a step of deprotecting acetoxystyrene through an acid-catalyzed process to form phenol groups, and further protecting the phenol groups with tBOC (paragraph 17-20). Wang further discloses formulating and patterning the chemically amplified resist compositions (paragraph 85).
However, Wang is silent to explicitly using vinylphenol as the polymerizable monomer such that a deprotection step to alter the acetoxystyrene to a phenol group is not needed. Furthermore Wang is silent to alternative acid-labile groups represented by Y2 represented by the formula (AY-4).
Malik discloses a process for generating mixed acetal polymers by reacting a hydroxyl containing polymer or monomer with vinyl ether and alcohol in the presence of acid catalyst (abstract). Example 1 shows the synthesis of mixed phenethyl and tertiary-butyl acetals of polyhydroxystyrene using polymerized polyhydroxystyrene (PHD) as the starting polymer (Col 16, Ln 45-65). Further, Malik contemplates the degree of acetalization by modulating the vinyl ether to alcohol ratios in the synthesis of Examples 3-19 (Col 17, Ln 40-65, also Table 1). The reaction in Example 1 with tertiary-butyl vinyl ether and phenethyl alcohol would form an acetal of the formula (AY-4) where Rc11 and Rc12 are hydrogen or a methyl group and Rc2 is an alkyl group. Additionally, Malik discloses that the copolymers may further be modified to incorporate t-BOC (Col 9, Ln 55-65). Malik formulates the examples into photoresist compositions with excellent resolution and good sensitivity (Col 21, Ln 12-15).
The teachings of Wang and Malik demonstrate the feasibility of starting with hydroxystyrene as the monomer feedstock in the resin since it is capable of undergoing different reactions with tBOC as demonstrated by Wang or acetal groups as demonstrated by Malik. It would have been obvious for one of ordinary skill in the art to have modified the acetoxystyrene monomer in Wang with hydroxystyrene as shown by Malik. One of ordinary skill would reasonably expect such a modification to result in a final polymer having the desired acid-labile group.
Furthermore, it would have been obvious for one of ordinary skill in the art to have substituted the t-BOC acid-labile protecting group in Wang with the acetal protecting group of Malik. Both protecting groups perform the same function and are deprotected upon exposure to acid and are used in resist compositions. One of ordinary skill would reasonably expect this modification to form a photoresist composition with similar patterning capabilities.
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 KEVIN JAMES DRUMMEY whose telephone number is (703)756-5419. The examiner can normally be reached Monday - Friday 7:30am-5:00pm EST.
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/K.J.D./Examiner, Art Unit 1737
/MARK F. HUFF/Supervisory Patent Examiner, Art Unit 1737