CTNF 18/483,895 CTNF 75663 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Claim Objections 07-29-01 AIA Claim s 1-20 are objected to because of the following informalities: The instant independent claim 1 recites that R11 to R13 optionally comprises a heteroatom, then recites that at least one of R11 to R13 comprises an iodine atom. It appears as though applicant intended to be worded such that at least of R11 to R13 comprises an iodine and each may optionally comprise a heteroatom in addition to the at least one iodine . Appropriate correction is required. Claim Rejections - 35 USC § 103 07-06 AIA 15-10-15 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. 07-20-aia AIA 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. 07-21-aia AIA Claim (s) 1-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Wada et al (7,341,817) . Wada et al disclose a photoresist composition comprising a photoacid generator, a resin, a dissolution inhibitor, a basic compound (instant quencher), a surfactant, and a solvent, wherein the acid generator has a basic structure similar to that as instantly claimed for A11+ and B11- (see examples, claims; instant claim 15-17). PNG media_image1.png 276 296 media_image1.png Greyscale PNG media_image2.png 86 310 media_image2.png Greyscale In the formulas, the instant X is S (instant claims 1 and 2), with the instant R11 to R13 equating to the reference R201 to R203, and they may be a cyclohydrocarbon (cycloalkyl, aromatic) or linear or branched alkyl. Any two may join to form a ring, and any may include a substituent such as alkyl, cycloalkyl, halogen, and alkoxy, and may be present on any or each, and wherein halogen would include iodine, and as examples below with one ring or three rings having substituents the compound clearly contemplates one to three substituents, and the structure would mee the exemplified structures of 1A-1, 1A-11 having at least one to three as in the instant claim 7 (see examples below; instant claims 3-7). PNG media_image3.png 176 294 media_image3.png Greyscale The anion includes a sulfonic acid bonded to a phenyl ring as in the instant formula, and further includes at least one substituent having a structure as claimed for the instant n11 group. For examples, in the examples below, the instant L21 may be a single bond or linking group, the instant L22 may be a single bond or linking group, and instant R21 cycloalkyl such as cyclohexyl, adamantyl, as seen below. The reference equates the alkyl groups with the cycloalkyl, and in the examples below, the alkyl group may be replaced by cycloalkyl. For examples L21 and L22 may be a single bond, L21 a single bond with L22 being alkyl, L22 a -CH2CH2O- group, as examples, and c11 may be 1 to 4, with F (instant claims 8-14, wherein R22 is H). The fourth structure is present on page 9 in the instant claim 14, and the similar compound with an adamantyl group as seen below is also set forth in the instant claim 14. PNG media_image4.png 88 178 media_image4.png Greyscale PNG media_image5.png 106 210 media_image5.png Greyscale PNG media_image6.png 86 216 media_image6.png Greyscale PNG media_image7.png 102 256 media_image7.png Greyscale PNG media_image8.png 216 536 media_image8.png Greyscale PNG media_image9.png 96 266 media_image9.png Greyscale PNG media_image10.png 244 286 media_image10.png Greyscale PNG media_image11.png 214 302 media_image11.png Greyscale PNG media_image12.png 200 318 media_image12.png Greyscale The compound is present in an amount of 0.1 to 20 mass %, wicb falls within the scope of the 0.1 to 40 % by weight as set forth by the instant claim 18. The resist is employed in a method comprisng the steps as set forth by the instant claims 19 and 20 including coating the resist onto a substrte, exposing to DUV, and developing the resist(examples, column 184, the paragraph that spans column 144 to 145 indicates that UV, DUV, Eb, EUV are also sutiable). Given the teachings of the reference, it would have been obvious to one of ordinary skill in the art prior to the effective filind date of the instant invention to prepare the material of Wada et al, choosing as the cation substitutent, iodien ats the halogen atom, with the resultant compound and composition also meeting the limitations of the instant claims . 07-21-aia AIA Claim (s) 6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Wada et al in view of Hatakeyama et al (11,720,021) . Wada et al has been discussed above. The reference teaches sulfonium cations which may have halogen/ iodine substiution, and that two of th ethree groups bonded to the sulfur atom mat join to form a ring. The reference exemplifies non-limiting options , but fails to specifically disclose a ring structure as set forth 1A-12. Hatakeyama et al disclose sulfonium cations having a similar geeral strcutre as that of Wada et al, wherein the reference teaches that rings formed by alkyl chains joing to form a ring and those wherein a linking group between aryl groups joins to form a ring are known and equivalent: PNG media_image13.png 344 282 media_image13.png Greyscale PNG media_image14.png 90 272 media_image14.png Greyscale Given the teachings of the references, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the instant invention to prepare the material of Wada e tal, choosing as the sulfonium cation which joins to form a ring, that as taught by Hatakeyama et al as known and equivalent to those disclosed by Wada et al, wherein the resultant compound would fall within the scope of the instant formula 1A-12 . Conclusion 07-96 AIA The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. References teaching similar cations and anions are known. Ober et al (2015/0021289) teach that Te and Se cations are known, but none of the cited references teaching the cation structure fairly provide motivation to one of skill in the art to replace S or I with Se or Te . Fujiwara et al (2020/0089112) disclose a resist composition comprising a photoacid generator (PAG; salt), a base polymer, a quencher, and a solvent (tables 1-3, claims 1 and 3-5; instant claims 15-17), wherein the salt has a basic structure meeting the limitations of the instant claims: PNG media_image15.png 104 388 media_image15.png Greyscale In the formula, the structure has the A11+B11- structure, where A11+ includes the instant X as S, and R11 to R13 as a combination of R5(3-r) and the group r, wherein R5 is a hydrocarbon group, and wherein two R5 may bond to form a ring, wherein preferred examples of R5 are phenyl groups, come join to for a cyclic or heterocyclic ring ([0059]). The “r” group includes at least one iodine atom. PNG media_image16.png 154 200 media_image16.png Greyscale PNG media_image17.png 222 242 media_image17.png Greyscale However, the reference teaches that the anion X may be a carboxylic acid anion, amic acid anion, and fluorine-free sulfonic acid anion ([0061]) wherein the instant B11- must comprise fluorine. Miyoshi et al (2021/0165325) al disclose a resist composition and PAG having a sulfonic acid anion, wherein the compound has a basic structure falling within the scope of the instant B11-. PNG media_image18.png 304 320 media_image18.png Greyscale PNG media_image19.png 458 300 media_image19.png Greyscale PNG media_image20.png 284 284 media_image20.png Greyscale PNG media_image21.png 170 508 media_image21.png Greyscale However, reference citing similar cations to those as claimed require fluorine-free anions or anions wherein the SO3- group in linked to a tertiary fluorinate carbon atom. Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMANDA C WALKE whose telephone number is (571)272-1337. The examiner can normally be reached Monday to Thursday 5:30am to 4pm. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Niki Bakhtiari can be reached at 571-272-3433. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /AMANDA C. WALKE/ Primary Examiner, Art Unit 1722 Application/Control Number: 18/483,895 Page 2 Art Unit: 1722 Application/Control Number: 18/483,895 Page 4 Art Unit: 1722 Application/Control Number: 18/483,895 Page 5 Art Unit: 1722
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