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.
Response to Amendment
Applicant’s Amendments filed 12/09/2025 has been considered and entered. Claims 1 and 4 have been amended, claims 7 and 9 have been amended to corrected dependency.
Response to Arguments
Applicant’s Amendments to claims 7 and 9 have corrected the issues regarding the 35 USC 112(b) rejection made in the prior office action. These rejections are withdrawn.
Applicant’s Amendments to the claims has changed the scope of the claims and as such these rejections are withdrawn.
After further search and consideration, the Examiner sets forth a new grounds of rejection as detailed below. These new grounds are necessitated by Applicant’s amendments to the claims.
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) 1-11 are rejected under 35 U.S.C. 103 as being unpatentable over Sasami et al US 20200218154 A1).
Regarding Claim 1-3,6, and 8-11, Sasami discloses a resist composition comprising a polymer compound having acid-generating moieties thereupon, as well as other structural units. The composition also comprises a solvent (Abstract).
The reference however does not disclose an experimental example wherein a polymer having the formula limitations of the claim are met.
These limitations are met by the general disclosure of the reference.
The composition of Sasami is generally disclosed from [0009]-[0108], where specific components such as the resin are described from [0029]-[0074], sulfonium/iodonium salts that may be added to the composition are described from [0075]-[0086, solvents are described from [0087]-[0089], and other component such as nitrogen-containing compounds and surfactants are discussed from [0090]-[0110].
The polymer resin of Sasami comprises one or two of the subunits (p-1) through (p-3), a unit (a-1), a unit (a-2), and a unit (b-1), as described in [0009]-[0010] and [0029]-[0050].
The repeating units (p-2) conform to the following formula:
PNG
media_image1.png
160
368
media_image1.png
Greyscale
Where:
R4 is a H, Me
Z2 is a single bond, or a group comprising a C1-12 alkanediyl group and a carboxyl or ether group where the alkanediyl group may also be carbonyl/ester/ether substituted.
R5 is an H or CF3 group
M1+ is a sulfonium, iodonium , or ammonium cation
Exemplary structures of the sulfonium cation include those shown in [0046] such as the one below:
PNG
media_image2.png
164
166
media_image2.png
Greyscale
The above subunit meets the limitations of the claimed repeating unit B comprising an organic acid moeity and a sulfonium cation having an organic aromatic ring structure with a fluorine atom, and further reads upon claim 3 at formula (3) where RA is H/Me, RY and RZ are each F, Y2 is a -C(=O)-O-Y21 group where Y21 is a C2 alkanediyl group having one carbon difluoro-substituted, or a C3 alkanediyl group having one carbon substituted with 3x F and one carbon substituted with 2x F atoms.
The repeating unit (a-1) is discussed from [0051]-[0057], conforming to the general structure below:
PNG
media_image3.png
226
384
media_image3.png
Greyscale
Exemplary monomers conforming to this formula are disclosed in [0055], of which some are replicated below
PNG
media_image4.png
300
336
media_image4.png
Greyscale
PNG
media_image5.png
180
242
media_image5.png
Greyscale
Where the above units read upon the claimed Cy and Rx of the instantly claimed repeating unit A as per formula (1) for where:
Rx is a C2-C4 hydrocarbon group
Cy is a C7-C10 polycyclic alicyclic hydrocarbon group (norbornyl, adamantyl)
An additional unit (b-1) is described from [0064]-[0067],
PNG
media_image6.png
416
362
media_image6.png
Greyscale
Specific embodiments of the monomer are depicted in [0066]:
PNG
media_image7.png
190
134
media_image7.png
Greyscale
PNG
media_image8.png
162
134
media_image8.png
Greyscale
PNG
media_image9.png
126
94
media_image9.png
Greyscale
The above monomer meets the limitations of the reference (as incorporated into the resin of prior art) where it comprises an iodine-substituted aromatic ring structure, and further reads upon the limitations of claim 6 for having a phenolic hydroxy group.
The composition comprises other components, such as solvents ([0087] like cyclohexanone, and acid generators such as acid diffusion controlling agents that produce acids having pKa values higher than those of the resin (claims 2 and 9)
Acid diffusion controlling agents include that of experimental examples at [0118] and Table 2-1, where polymer P-15 is mixed in a solvent (PGMEA) along with onium salt 1-3 to make Resist R-15:
PNG
media_image10.png
146
336
media_image10.png
Greyscale
This compound functions as an acid diffusion controller as it will generate an acid having a pKa higher than that of the fluorosulfonic acid of the resin P-15. (This salt is also present in applicant’s own specification at [0204] Formula 55). As per claim 9, the salt comprises an iodinated aromatic ring.
In order to form patterned films, the compositions of Sasami are coated onto a substrate having an antireflection film thereupon, baked on a hot plate, exposed to EUV using an NXE3300 apparatus, post-exposure baked, and then developed using an aqueous TMA developer ([0122]) (claims 10 and 11).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the filing date from the general disclosure of the reference, which discloses materials and methods for arriving at a photoresist composition and patterned resist film having high resolution and good pattern shape.
Regarding claims 4, 5, and 7, Sasami discloses a resist composition comprising a polymer compound having acid-generating moieties thereupon, as well as other structural units. The composition also comprises a solvent (Abstract).
The composition of Sasami is generally disclosed from [0009]-[0108], where specific components such as the resin are described from [0029]-[0074], sulfonium/iodonium salts that may be added to the composition are described from [0075]-[0086, solvents are described from [0087]-[0089], and other component such as nitrogen-containing compounds and surfactants are discussed from [0090]-[0110].
Sasami however does not disclose an experimental embodiment having an onium salt comprising an organic acid anion moeity and a sulfonium cation having an aromatic ring structure with a fluorine atom.
This limitation is met by the general disclosure of the reference as detailed below:
The resin comprises one or two subunits having acid-generating moieties p-1 through p-3:
PNG
media_image11.png
416
346
media_image11.png
Greyscale
Where R1, R4, and R6 are H or Me groups; Z1 is a single bond, phenylene, or group outlined in [0043]; Z2 is a single bond, -Z21-COO-, Z21-O-, or Z21-O(C=O)- group where Z21 is an alkanediyl group having 1-2 carbons that may be substituted with carbonyl, ester or ether bonds; R2 and R3 are each a monovalent hydrocarbon group that may be substituted; R5 is a H or CF3 group; Z3 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, -Z31-(C=O)O-, Z31-O-, or Z31-(C=O)-NH-, where Z31 is an alkylene group of 1-6 carbons that may comprise carbonyl, ester, or ether substitution. M1+ represents a counteraction that may be sulfonium, ammonium, or iodonium. M0- represents a counter anion that is nonnucleophilic, such as a sulfonate.
Formula p-3 reads upon the instantly claimed invention of claim 4 for where it is a subunit having an onium cation moeity and acid anion moeity.
Further, it reads upon claim 7 for general formula (5) where:
RB is H or Me
Y2 is Z3, where Z3 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, -Z31-(C=O)O-, or Z31-(C=O)-NH-. where Z31 and Y21 overlap for alkanediyl groups of 1-6 carbons that may optionally have carbonyl groups, ester linkages, or ether linkages
Additional repeating units (a-1) are disclosed from [0051]-[0057], conforming to the general formula below:
PNG
media_image12.png
136
350
media_image12.png
Greyscale
R7 is a methyl or hydrogen atom
Y is a group that changes the polarity of the unit by action of an acid so as to increase solubility in alkali.
Examples of these units are given in [0055]
PNG
media_image4.png
300
336
media_image4.png
Greyscale
PNG
media_image5.png
180
242
media_image5.png
Greyscale
Where the above units read upon the claimed Cy and Rx of the instant claim for where:
Rx is a C2-C4 hydrocarbon group
Cy is a C7-C10 polycyclic alicyclic hydrocarbon group (norbornyl, adamantyl)
Additional units are described from [0058]-[0074], (b-1) is described from [0064]-[0067],
PNG
media_image6.png
416
362
media_image6.png
Greyscale
Specific embodiments of the monomer are depicted in [0066]:
PNG
media_image7.png
190
134
media_image7.png
Greyscale
PNG
media_image8.png
162
134
media_image8.png
Greyscale
PNG
media_image9.png
126
94
media_image9.png
Greyscale
The above monomer meets the limitations of the reference (as incorporated into the resin of prior art) where it comprises an iodine-substituted aromatic ring structure.
A salt may be present in the composition, where the salt conforms to the formula (B), or (B1) ([0075]-[0081],
PNG
media_image13.png
26
332
media_image13.png
Greyscale
PNG
media_image14.png
84
350
media_image14.png
Greyscale
Where M2+ is a cation that may be ammonium, iodonium, or sulfonium; Ma is a linear/branched/cyclic hydrocarbon that may be substituted and bears 1-35 carbon atoms.
R18-R19 may be H, F, CF3; R20 is linear/branched/cyclic C1-C20 alkyl, C6-C30 carbon aryl, OH, or Hydrogen. Example anions are presented in [0081]. The carboxylic anion has a lower acid strength than the sulfonium salt of the resin and as such this salt functions as a quencher or acid-diffusion control agent ([0081].
A fluorosulfonate salt (B2) that functions as an additional acid generator is disclosed from [0082]-[0086].
The reference does not specifically exemplify the cations of these salts, but does present sulfonium, iodonium, and ammonium cations elsewhere in the reference at [0046]-[0048]:
PNG
media_image15.png
172
170
media_image15.png
Greyscale
PNG
media_image16.png
134
234
media_image16.png
Greyscale
An ordinarily skilled artisan would have found it obvious to arrive at the claimed invention prior to the filing date from the general disclosure of Sasami - a person of ordinary skill in the art would naturally look to the total disclosure of the reference for arriving at one or both of the salts (B1) and (B2) and would find it obvious to try a mixture of cations from [0046]-[0048] with the taught anions of (B1) and/or (B2) to arrive at an optimized composition having an acid generator and/or acid diffusion controller to improve the patterning of the composition’s resultant films.
Claim(s) 8 is rejected under 35 U.S.C. 103 as being unpatentable over Sasami et al US 20200218154 A1).
Regarding Claim 8, Sasami discloses the limitations of the claim as discussed above regarding claim 1 above.
Sasami does not, however, disclose an experimental embodiment meeting the limitations of claim 1 that also meets the limitations of claim 8 for the structural unit (6) as claimed.
This limitation is met by the general disclosure of the reference. Polymer P-15 (see discussion regarding claim 1) discloses a subunit E-2 out of several different embodiments of E subunits.
The reference also discloses subunit E4 and E5:
PNG
media_image17.png
348
352
media_image17.png
Greyscale
E4 and E5 read upon the instantly claimed formula (6) for where (when polymerized):
RT is a methyl group
X is a methanediyl group or oxy (-O-) group
Subscript n6 is 0
The reference presents the E subunits as alternatives to one another (See Table 1, also see {0068]-[0074], where all of these subunits bear a lactam group therein. A person of ordinary skill in the art would have found it obvious to try the substitution of one alternative unit for another with recognition that they should behave similarly due to chemical similarity and because the art recognizes them as alternatives.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention from the generally disclosed embodiments of lactam-bearing subunits in Sasami’s polymer resin, recognizing that art-recognized alternatives and chemically similar embodiments should behave in a similar manner and enable the generation of a resist composition having improved LWR and patterning performance.
Claim(s) 12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sasami et al US 20200218154 A1) as applied to claims 1 and 3 above, and further in view of Anryu et al (US 20190315684, published 11/17/2019).
Regarding Claim 1, Sasami discloses the limitations of the claim as discussed above regarding claims 1 and 3 above.
Sasami however does not disclose an instance wherein the sulfonium cation electrostatically bound to a polymer subunit anion group conforming to the limitations of formula (2) or (3) further conforms to the limitations that R1-R3 or R4-R6 are each independently a monovalent hydrocarbon and at least one of these groups is an aromatic ring having four or more fluorine atoms or at least two of these groups each is an aromatic ring having two or more fluorine atoms.
This limitation is met by Anryu.
Anryu discloses a photosensitive composition comprising a base resin and a photoacid generator, wherein the photoacid generator bears a cation described from [0022]-[0041], and an anion as described from [0042]-[0158], where the cation is preferably one of an embodiment selected from those below, but generally conforms to formula (I) presented in the reference at [0005]-[0011]:
PNG
media_image18.png
238
334
media_image18.png
Greyscale
PNG
media_image18.png
238
334
media_image18.png
Greyscale
The above cation reads upon the instantly claimed formula’s cation where at least two aromatic rings bear at least two fluorine atoms. The reference describes that resist patterns produced from compositions using the salt bear satisfactory line edge roughness. Incorporating the salt into the resist composition of Sasami, which is dissolved in solvent, necessitates a degree of ion exchange which would arrive at the cation-anion pairing of the anion of claimed formula (3) as discussed above regarding Sasami with one of the above cations. This inclusion, and/or the outright substitution of a fluorinated sulfonium cation already taught by Sasami for another fluorinated sulfonium cation (as above) would be expected to arrive at improved patterning properties as prompted by Anryu.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the filing date in view of the disclosures of Anryu and Sasami, incorporating the cation of Anryu into the polymeric salt subunits of Sasami in order to improve line edge roughness.
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 ANDREW PRESTON TRAYWICK whose telephone number is (571)272-2982. The examiner can normally be reached Monday - Friday 8-5.
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, Mark Huff can be reached at 571-272-1385. 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.
/A.P.T./Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734
Prosecution Insights