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 § 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.
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.
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.
Response to Arguments
Applicant's arguments filed 9/8/2026 have been fully considered but they are not persuasive. Applicant has amended the claims to clarify the definition of R11 to R13 regarding the heteroatom, and the claim objections have been withdrawn.
Regarding the art rejections over Wada et al, applicant has argued that the reference fails to fairly teach or suggest the salt as claimed wherein the salt comprises the cation and anion as claimed. Applicant argues that the cation of Wada belongs to a broad genus of sulfonium cations and does not expressly disclose at last one of the three hydrocarbon groups comprise at least one iodine atom (response, page 22, C.) As discussed above, the reference teaches a sulfonium cation having three substituents, R201 to R203, which are defined as being selected from linear, branched, or cyclic alkyl groups and aromatic groups, wherein the R201 to R203 groups may have a substituent selected from the small group of alkyl, cycloalkyl, aryl, hydroxyl, halogen, phenylthiol, and alkoxy groups (column 28, line 53 or column 29, line 3). One of ordinary skill in the art would immediately recognize halogen as one of the finite list of F, Br, I, and Cl. Furthermore, exemplified cations include at least one, and preferably three (one per ring/group) substituents.
Given the small list of seven classes of substituents, and the finite list of halogens, one of ordinary skill in the art would have been motivated to include a halogen, with the halogen atom being iodine. Additionally, similar substituents are listed for R204 and R205 to the iodonium cation, with the substituents on the aryl groups specially notes I, Br, and Cl are preferred aryl group substituents, further indicating that iodine is a halogen contemplated by the reference. Furthermore, the reference specifically notes iodine in its list of halogens for substituents on the anion, further indicating that iodine is contemplated for use as the halogen broadly in the compounds.
Applicant has also argued that Wada does not discuss achieving the properties the instant invention seeks to achieve by including the specific substituents, however, the fact that the reference does not aim to solve the same problem as applicant and does not have the same motivation to include the compound in its material does not overcome a rejection (response, page 25, paragraph 1-3).
Applicant has further argued that the instant specification discloses the advantages of including iodine over other halogen atoms. As discussed in the interview of 7/20/2026 and now presented in the response, the applicant has argued that iodine has a high light absorption rate, resulting in a cation/ salt having enhanced absorbance, lower molecular weight, and improved resolution (response, page 24, paragraph 2). As discussed in the interview, a showing of these improvements in combination with these arguments would likely overcome the rejections over Wada, however, upon consideration of the examples in the specification, the examples are not commensurate in scope with the claims nor demonstrate unexpected and superior results are argued by applicant.
The exemplified compounds in the specification are not commensurate in scope with the instant independent claim, and do not provide any direct comparisons to the closest prior art and/or compounds not having at least one iodine atom on an R11 to R13 group. The exemplified compounds as highlighted by applicant (see response, page 19) in examples 1 and 4 have the same structure with the exception of the cation containing two iodine atoms. Further examples are presented in [0241], Table 1, compound A-D and 1-4 ([0425], [0252], wherein each cation comprises one or two iodine atoms, and no examples have triphenyl sulfonium cations with no halogen/ iodine atoms, or say with a fluorine or alkyl/ alkoxy/ hydroxyl as a substituent instead of an iodine, similar to the those of Wada, or to demonstrate any unexpected results in Z factor (resolution and sensitivity) and dark-loss by showing the improvements between cations not having an iodine atom and those having at least one, or a group as preferred by the closed prior art. Only one example presents a comparison between compounds having an R21 group as claimed as compared to an aryl group in the same position (D and 3), with the examples having preferred R21 groups which are not commensurate in scope with the compounds defined by claim 1. The examples do not demonstrate the results argued by applicant as demonstrating that the compounds of the instant invention possess unexpected and superior properties.
Therefore, upon consideration of the arguments and the examples of record in the instant specification, the arguments are unpersuasive and the rejections of record are maintained.
Conclusion
THIS ACTION IS MADE FINAL. 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 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
Prosecution Insights