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, 4-6 and 9-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ichikawa et al (JP 2021-035936 and its machine translation).
Ichikawa et al disclose a resist composition comprising a PAG having a sulfonium cation and a sulfonate anion, wherein the cation and anion have structures meeting the limitations of the instant claims.
The cation has a structure meeting the limitations of the instant formula (1) (instant claim 1).
PNG
media_image1.png
120
374
media_image1.png
Greyscale
PNG
media_image2.png
150
396
media_image2.png
Greyscale
In the formula, the instant L is a single bond, s is 1, R4 is alkyl, and at least one of p, q, r is 1, with R1-R3 being halogen in most examples (F).
The polymer (instant claim 4) preferably comprises an additional unit having an acid-labile group, falling within the scope of the instant (a1), wherein RA is H or methyl, and R11 is a alkyl-cycloalkyl group as required by the instant claim 5.
PNG
media_image3.png
142
470
media_image3.png
Greyscale
The resist is preferably a positive resist (instant claim 6), and further includes a solvent (instant claim 9), a quencher (instant claim 10), as demonstrated in examples ([0223]).
The patterning process includes the steps as claimed, wherein the composition is applied, dried/pre-baked, exposed, and developed, with the light exposure performed by ArF, KrF, EUV, or electron beam ([0211], examples; instant claims 12 and 13).
The reference teaches a salt and resist composition as discussed above, but the reference further teaches that the composition may comprise a surfactant ([0208], [0209]; instant claim 11), and an acid-labile group-containing unit of the instant formula (a2), and have an anion meeting the limitations of the instant formulas.
First, the salt may further comprise halogen or perfluoralkyl groups on any of the rings (see R4 to R6, instant R1-R3), and is not limited to the preferred examples.
Therefore, the reference teaches one of ordinary skill in the art prior to the effective filing date of the instant invention to prepare the material of the reference, choosing for the instant R1 to R3 (and in turn p to r to be each 0 to 3) to be halogen or trifluoromethyl (abstract).
The anion of the reference has a structure similar to that of the instant formula (2)-1 and (2)-2 (instant claims 2 and 3).
PNG
media_image4.png
84
260
media_image4.png
Greyscale
In the formula z can be 1 and R1 and R2 fluorine atoms ([0012]), and wherein X1 and L1 (instant X1 and X2, and X3 and X4, respectively) are linking groups including -COO-, -OCO-, O-CO-O-, and a single bond, alkyl group ([0012]). Examples appear below, wherein the end group include an phenyl substituted by a halogen. While the halogen atom exemplified is F, one of ordinary skill in the art would have envisaged another from the finite group of halogens, including iodine ([0014]-[0018]).
PNG
media_image5.png
98
320
media_image5.png
Greyscale
When the compound is as described above, wherein z 1 1 and R1 and R2 are F, and the fluorine atom on phenyl ring is replaced by iodine, the anion meets the limitations of the instant claim 1. Regarding newly added claim 14, the aryl ring may have any of the five positions substituted, therefore one of ordinary skill in the art would have envisaged 1 to 5 substituents.
The acid-labile groups-containing unit may have the structure of the instant (a2), taught to be equivalent to that of (a1) above.
PNG
media_image6.png
132
176
media_image6.png
Greyscale
PNG
media_image7.png
110
252
media_image7.png
Greyscale
Therefore, 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 Ichikawa et al , choosing as the anion, that as taught by the reference wherein the end group is a phenyl group having an iodine substituent, wherein the acid-labile group-containing unit is that as that of instant formula (a2), or wherein material further comprises a surfactant as a known additive, each as taught to be known by the reference.
Claim(s) 1 and 4-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over LaBeaume (10,274,825) in view of Ichikawa et al.
LaBeaume disclose a resist composition comprising an acid generator having a structure falling within the scope of the instant claims.
PNG
media_image8.png
258
260
media_image8.png
Greyscale
PNG
media_image9.png
122
222
media_image9.png
Greyscale
PNG
media_image10.png
142
186
media_image10.png
Greyscale
PNG
media_image11.png
140
206
media_image11.png
Greyscale
PNG
media_image12.png
168
208
media_image12.png
Greyscale
In the formula, D (instant L) is a single bond, carbonyl, CH2, ether, sulfide, sulfonyl, s is 1 and includes the instantly claimed -OR4 acid labile group, e-g (instant p-r) are 0-4, and A-B (instant R1 to R3) is hydrogen or a substituent such as halogen (fluorine), trifluoromethyl meeting the limitations of the instant formula (1) of claim 1 (preferred substituents, column 5, line 62 to column 6, line 64, nitro, methoxy, F, CF3, aryl, -OH used in examples).
The resist further comprises a polymer (instant claim 4; claim 25), wherein the polymer includes positive and negative-acting resists, wherein the resist includes an acid-labile groups, or a polar group (positive and negative [phenols], respectively; column 10, lines 29-59, column 17, lines 36-55, each equally preferred; instant claims 6-8).
The positive resist includes acid-labile group-containing units includes t-butyl (meth)acrylate (formula (a1); instant claim 5).
PNG
media_image13.png
268
402
media_image13.png
Greyscale
The resist further comprises a solvent, a surfactant, and a base/ quencher (see examples and column 17, line 61 to column 18, line 40 which describes the additives in the examples; instant claims 9-11).
The method of the reference includes the steps of applying, drying/ pre=baking, exposing to EUV or ebeam, then developing (column 19, lines42-67, examples; instant claims12 and 13).
LaBeamue teaches that suitable anions of their sulfonium cation include known anions, and preferred compounds include fluorinates sulfonic acids (column 4, line 51 to column 5, line 3), however, the reference fails to specifically teach the claimed anion.
However, as discussed above, Ichikawa et al disclose a similar sulfonium cation and fluorinated sulfonic acid anion, wherein the disclosed anions fall within the scope of the instant claims 1 and 14 (formulas (2)-1 and (2)-2).
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 LaBeaume, choosing as the fluorinate sulfonic acid anion, that taught to be known and useful with similar cations by Ichikawa et al. The resultant cation and anion would also meet the limitations of the instant claims.
Response to Arguments
Applicant's arguments filed 9/4/2026 have been fully considered but they are not persuasive. Applicant has amended claim 1 to incorporate the limitations of claims 2 and 3, now cancelled.
The amendments overcomes the 102 rejections over Ichikawa and LeBeaume. Each reference rejected claims 2 and 3 under 103, and the 102 rejections have been withdrawn, and 103 rejections reformulated in response to the claim amendments.
Applicant has argued that the Ichikawa reference (which is relied upon is all art rejections as it is included in the 103 over LeBeaume) fails to fairly teach or suggest the claimed salt comprising an anion having an aryl ring with at least one iodine atom, and a cation having the structure as set forth by the instant formula (1).
Applicant has argued that the instant specification teaches that the inclusion of an iodine atom having a large absorption of EUV light on the anion increases the absorption of the photoacid generator and the degradation efficiency in exposure (response, paragraph spanning pages 9 to page 10), which applicant argues improves LWR and CDU.
Applicant specifically notes that the office relies on Ichikawa as teaching a cation falling within the scope of the instant claims, and an anion wherein the phenyl ring includes a halogen atom, which may be iodine. Specific examples of the anion have a basic structure meeting the limitations of the instant formulas (2)-1 and (2)-2, including specific examples of (2)-1, wherein the ring includes halogen substitution, wherein the halogen in those examples in fluorine. As set forth above, the ring may ben substituted by a halogen atom, wherein a finite group of possible halogen atoms includes fluorine and iodine. One of ordinary skill the art would have envisaged using any halogen, not only fluorine. While the reference more preferably includes fluorine, the reference is not limited to its most preferred teachings and only to its examples, therefore applicant’s arguments that the reference prefers fluorine is not persuasive (response, page 10 to page 11).
Additionally, applicant argues that the reference fails to recognize the benefit of iodine over fluorine, but again, halogens include F, Br, Cl, and I, which is a small group, and by the reference teaching the ring may have a halogen substituent, one of skill in the art would have envisaged using any halogen including iodine (response, page 11, last paragraph). Applicant has further argued in the paragraph that the reference fails to recognize the specific benefit for including iodine over other halogen atoms (increased absorption of EUV light that improves degradation efficiency, absorption contrast, and LWR and CDU improvement), however, the reference does not need to have the same motivation as applicant for adding a compound to a composition or modifying a compound, and the fact the reference does not aim to solve the same problem and achieve the same benefits as applicant does not overcome a rejection.
Applicant further argues that LaBeaume in view of Ichikawa also fails to fairly teach the claimed salt, and argues that Ichikawa fails to cure the deficiency of LaBeaume regarding the PAG anion structure (response, page 13, paragraph 2). Arguments to the combination of references are to the teachings of Ichikawa which have been discussed at length above to the rejection over Ichikawa alone, and the Labeaume in view of Ichikawa rejections are maintained as the arguments are unpersuasive as the were to Ichikawa alone.
The double patenting rejection is withdrawn in light of the amendment.
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 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