Prosecution Insights
Last updated: August 18, 2026
Application No. 18/319,757

DRY PHOTORESIST OR HARDMASK FOR EUV LITHOGRAPHY

Final Rejection §102§103§112
Filed
May 18, 2023
Examiner
ANGEBRANNDT, MARTIN J
Art Unit
1737
Tech Center
1700 — Chemical & Materials Engineering
Assignee
International Business Machines Corporation
OA Round
2 (Final)
55%
Grant Probability
Moderate
3-4
OA Rounds
0m
Est. Remaining
90%
With Interview

Examiner Intelligence

Grants 55% of resolved cases
55%
Career Allowance Rate
759 granted / 1370 resolved
-9.6% vs TC avg
Strong +34% interview lift
Without
With
+34.2%
Interview Lift
resolved cases with interview
Typical timeline
3y 1m
Avg Prosecution
66 currently pending
Career history
1448
Total Applications
across all art units

Statute-Specific Performance

§101
0.4%
-39.6% vs TC avg
§103
44.4%
+4.4% vs TC avg
§102
21.0%
-19.0% vs TC avg
§112
20.5%
-19.5% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1370 resolved cases

Office Action

§102 §103 §112
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 . The election of 2/5/2026 has been received. The restriction stands and claims 23-25 are withdrawn and the election is in force. The response of the applicant has been read and given careful consideration. Responses to the arguments are presented after the first rejection they are directed to. The following is a quotation of 35 U.S.C. 112(b): (b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention. The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. Claims 28-33 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claims 28-33 use a notation with a backslash (eg.. “R1/1”), the claims structures use a comma rather than the slash. Please correct this as it is not clear what is being referred to. 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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action: A person shall be entitled to a patent unless – (a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. 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. Claims 16-22 and 26-40 are rejected under 35 U.S.C. 103 as being unpatentable over Totsune JP 2009280724 as evidenced by Nah et al., “Comparisonal studies of surface modification reaction using various silylating agents for silica aerogel”, J. Sol.-gel Sci. Technol. Vol. 96 pp 346-359 (2020) Totsune JP 2009280724 (machine translation attached) teaches bismuth oxide precursors bounded by formula PNG media_image1.png 33 232 media_image1.png Greyscale Where R .sup.1 is an organic group, an alkyl group, a halogenated alkyl group, an aryl group, a halogenated aryl group, or a cycloalkyl group, R .sup.2 is an alkyl group or aryl group having 1 to 6 carbon atoms, and a is 0 or 1 It is. Here, examples of the alkyl group for R .sup.1 include a methyl group, an ethyl group, an isopropyl group, a normal butyl group, and an isobutyl group. Examples of the halogenated alkyl group include a trichloromethyl group, a trifluoromethyl group, and a pentachloroethyl group. Examples of the aryl group include a phenyl group and a styryl group. A methyl group and a phenyl group are preferable. Examples of the alkyl group or aryl group for R .sup.2 include a methyl group, an ethyl group, an isopropyl group, a normal butyl group, an isobutyl group, and a phenyl group [0011-0012]. The blending amount of bismuth oxide (III) is preferably 5% by mass or more and 50% by mass or less in the optical material composition. If the amount is less than 5% by mass, a material composition having a sufficient Abbe number and anomalous dispersion cannot be obtained. If the amount exceeds 50% by mass, the fluidity of the material composition is lost, and the processing of the optical element becomes difficult [0015]. In the examples 1-acryloxy-4-methoxynaphthalene as the organic compound (B1) having one polymerizable functional group and 9,9-bis [4- (2-acryloyl) as the organic compound (B2) having two polymerizable functional groups Oxyethoxy) phenyl] fluorene, a photopolymerization initiator bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide as a polymerization initiator (C), mixed in a blending amount described in Table 1 in mass% to obtain Mixing fine particles of bismuth oxide (III) (A) having an average particle size of 15 nm and a 90% particle size of 20 nm so as to be 5, 10, 30, 50% by mass with respect to the total amount of the obtained polymerizable composition, and wet The composition was prepared by dispersing in a bead mill for 1 hour using beads having a diameter of 0.05 mm. As a preparation method of the material composition of the present embodiment, fine particles (A) of bismuth oxide (III) are added to the organic compound (B) and the polymerization initiator (C), and a bead mill, a ball mill, a jet mill, a homogenizer, etc. And a known dispersion apparatus in which all components are uniformly dispersed to obtain a material composition. The dispersion state of the material composition is adjusted by setting the material and size of the media such as beads and balls used for dispersion and the conditions of the dispersion device. At this time, depending on the dispersion state of the material composition, a dispersant may be added as long as it is in an amount that does not impair the abnormal dispersibility and workability, and a solvent may be temporarily added. However, it is necessary to remove this solvent before finally processing as an optical element [0034]. PNG media_image2.png 459 568 media_image2.png Greyscale Nah et al., “Comparisonal studies of surface modification reaction using various silylating agents for silica aerogel”, J. Sol.-gel Sci. Technol. Vol. 96 pp 346-359 (2020) illustrates the hydrolysis/condensation of solgel reactions of methyltrimethoxysilane. PNG media_image3.png 359 462 media_image3.png Greyscale Totsune JP 2009280724 does not exemplify a composition including the elected bismuth compound in an amount of more than 5wt% as the exact composition of the bismuth oxide nanoparticles of the examples are not described. It would have been obvious to one skilled in the art to modify the examples of Totsune JP 2009280724 containing 5, 10, 30 or 50 wt% bismuth oxide nanoparticles by forming the bismuth oxide nanoparticles using methylbismuth dialkoxides which are embraced by formula PNG media_image4.png 52 363 media_image4.png Greyscale when a is 1, R1 is methyl and R2 is an alkyl group as taught at [0011-0012]. The resulting nanoparticles will include at least Me-Bi(OR2)-O- Bi(OR2)-Me, PNG media_image5.png 66 102 media_image5.png Greyscale , Me-Bi(OR2)-O--Bi(Me)-O- Bi(OR2)-Me, Me-Bi(OR2)-O--Bi(Me)-O-Bi(Me)-O- Bi(OR2)-Me, and PNG media_image6.png 171 169 media_image6.png Greyscale as the methyl group is not a leaving group in the hydrolysis/condensation of solgel reactions as evidenced in Nah et al., “Comparisonal studies of surface modification reaction using various silylating agents for silica aerogel”, J. Sol.-gel Sci. Technol. Vol. 96 pp 346-359 (2020), so the resulting bismuth oxide nanoparticles will includes bismuth oxide compounds bounded by b,c and e, as well as formulae (II) or III . The position of the examiner is that the resultant coating will inherently contain 5-50 wt% of bismuth oxide nanoparticles will includes bismuth oxide compounds bounded by b,c and e, as well as formulae (II) or III. Also due to the bismuth oxide content, the composition will be resistant to etching and as it is photopolymerizable and includes a photoinitiator, it is able to act as a photoresist. In the arguments of 6/5/2026, the applicant requests rejoinder. The claims are not in condition for allowance, so the request is premature. The added wt% limitation is met by the teachings in Totsune JP 2009280724 which also describes the use of PNG media_image4.png 52 363 media_image4.png Greyscale or hydrolyzates as bismuth oxide precursors. The examiner notes that the claims allow for trace amounts of solvent in composition and that the references describe temporarily including a solvent, but that this is removed before finally processing as an optical element. It is not clear if this refers to removing the solvent prior to curing or prior to lamination on the surface of an optical substrate [0008] Claims 16-22 and 26-40 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Wieber et al., “Zur synthese von tetramethyldibismutan und dessen spaltung zu bis(dimethylbismut)oxide oder -sufide bzw. Phenyldimethylbismutan”, Zeitshift fuer Naturforschung, Teil B, Anorganische Chimie, Organische Chemie, Vol. 39B(7) pp 887-889 (1984). Wieber et al., “Zur synthese von tetramethyldibismutan und dessen spaltung zu bis(dimethylbismut)oxide oder -sufide bzw. Phenyldimethylbismutan”, Zeitshift fuer Naturforschung, Teil B, Anorganische Chimie, Organische Chemie, Vol. 39B(7) pp 887-889 (1984) exemplifies PNG media_image7.png 52 309 media_image7.png Greyscale on page 887. bis(dimethylbismut)oxide is synthesized on page 888 by reacting dimethylbismut bromide with petroleum ether and oxygen is introduced to form a solution which is almost colorless. The bis(dimethylbismut)oxide is precipitated, washed several times with more petroleum ether and then dried. The decomposition temperature is 16 degrees C. bis(dimethylbismut)sulfide is synthesized on page 889 by reacting dimethylbismut bromide with petroleum ether and sulfur is introduced to form a solution. The bis(dimethylbismut)oxide is precipitated as a yellow solid, washed several times with more petroleum ether and then dried. The decomposition temperature is 28 degrees C. Bis(dimethylbismut)oxide is bounded by formula II, where R1-R3 are methyl, A is oxygen and n is 1. It is also embraced by formula b (claims 28 an d is recited in the claims as dimethylbismuthanyloxy(dimethyl)bismuthane (claims 37-39) The Bis(dimethylbismut)oxide where it is part of a solution./dispersion in petroleum ether meets the claims. While this is not the elected compound, it is structurally similar. The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Wieber et al., “Sauerstoff- und schwefelhaltige monoorganobismutine: dialkoxumethyl- und bis(alkylthio)methylbismutine, 2-methyl-1.3.2-diheterobismole und bismolane”, Z. Anorg., Allg. Chem., Vol. 423, pp 40-46 (1976) exemplifies PNG media_image8.png 54 377 media_image8.png Greyscale on page 41 and compounds PNG media_image9.png 190 430 media_image9.png Greyscale on page 42. Breunig et al., “Novel sterically congested monoorganobismuth(III) compounds: synthesis, structure and bismuth-arene p interaction in ArBiXY ..”, Organometallics Vol. 28(4) pp 1202-1211 (2009} teaches compounds similar to the elected compound, but include aryl groups, rather than alkyl groups as ligands. Miersch et al., “Organic-inorganic hybrid materials starting from the novel nanoscaled bismuth oxido methacrylate cluster….” Chem. Commun. Vol. 47 pp 6353-6355 (2011) teaches bismuth oxide clusters similar to the elected compound, but does not use alkyl ligands. Sharutin et al., “Organic compounds of bismuth: Synthesis, structure and applications.”, Russian J. Coordination Chem. Vol. 47(12) pp 791-860 (2021) teaches PNG media_image10.png 68 84 media_image10.png Greyscale (page 837) and PNG media_image11.png 55 92 media_image11.png Greyscale (page 838), but the ligands are not methyl or alkyl. 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 Martin J Angebranndt whose telephone number is (571)272-1378. The examiner can normally be reached 7-3:30 pm EST. 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, Ching-Yu (Coris) Fung can be reached at 571-270-5713. 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. MARTIN J. ANGEBRANNDT Primary Examiner Art Unit 1737 /MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 July 2, 2026
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Prosecution Timeline

May 18, 2023
Application Filed
Mar 10, 2026
Non-Final Rejection mailed — §102, §103, §112
May 08, 2026
Interview Requested
May 28, 2026
Applicant Interview (Telephonic)
May 28, 2026
Examiner Interview Summary
Jun 05, 2026
Response Filed
Jul 07, 2026
Final Rejection mailed — §102, §103, §112 (current)

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Prosecution Projections

3-4
Expected OA Rounds
55%
Grant Probability
90%
With Interview (+34.2%)
3y 1m (~0m remaining)
Median Time to Grant
Moderate
PTA Risk
Based on 1370 resolved cases by this examiner. Grant probability derived from career allowance rate.

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