Prosecution Insights
Last updated: April 19, 2026
Application No. 18/319,757

DRY PHOTORESIST OR HARDMASK FOR EUV LITHOGRAPHY

Non-Final OA §102§103§DP
Filed
May 18, 2023
Examiner
ANGEBRANNDT, MARTIN J
Art Unit
1737
Tech Center
1700 — Chemical & Materials Engineering
Assignee
International Business Machines Corporation
OA Round
1 (Non-Final)
55%
Grant Probability
Moderate
1-2
OA Rounds
3y 3m
To Grant
90%
With Interview

Examiner Intelligence

Grants 55% of resolved cases
55%
Career Allow Rate
745 granted / 1351 resolved
-9.9% vs TC avg
Strong +34% interview lift
Without
With
+34.5%
Interview Lift
resolved cases with interview
Typical timeline
3y 3m
Avg Prosecution
86 currently pending
Career history
1437
Total Applications
across all art units

Statute-Specific Performance

§101
0.1%
-39.9% vs TC avg
§103
59.6%
+19.6% vs TC avg
§102
4.2%
-35.8% vs TC avg
§112
2.1%
-37.9% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1351 resolved cases

Office Action

§102 §103 §DP
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 is repeated for completeness. The arguments are addressed below. Restriction to one of the following inventions is required under 35 U.S.C. 121: I. Claims 1-15, drawn to a boron compound bounded by the formulae of the claims, classified in C07F9/94. II. Claims 16-22, drawn to a boron compound bounded by the formulae and hardmasks or resists composed of them, classified in G03F7/0042 (inorganic resist) or G02F7/09 (hardmask). Claim 16 is grouped with claims 17-22 as it does not require anything other than coating, which does not involve a chemical transformation (as the exposure and development in the patterning does). III. Claims 23-25, drawn to a process of patterning the bismuth layer directly using exposure, classified in G03F7/20+ The inventions are independent or distinct, each from the other because: Inventions group I and group III are related as product and process of use. The inventions can be shown to be distinct if either or both of the following can be shown: (1) the process for using the product as claimed can be practiced with another materially different product or (2) the product as claimed can be used in a materially different process of using that product. See MPEP § 806.05(h). In the instant case the compound can be used as an intermediate material to form another compound. Inventions group II and group III are related as product and process of use. The inventions can be shown to be distinct if either or both of the following can be shown: (1) the process for using the product as claimed can be practiced with another materially different product or (2) the product as claimed can be used in a materially different process of using that product. See MPEP § 806.05(h). In the instant case the bismuth layer can be left unpatterned or patterned using a masked deposition or an etch mask of a different material. Groups I and II would be examined together as the mere deposition/formation of the layer does not necessarily result in any chemical transformation. Restriction for examination purposes as indicated is proper because all the inventions listed in this action are independent or distinct for the reasons given above and there would be a serious search and/or examination burden if restriction were not required because one or more of the following reasons apply: They have acquired a separate status in the art as evidenced by their different classification and would require a divergent search Applicant is advised that the reply to this requirement to be complete must include (i) an election of an invention to be examined even though the requirement may be traversed (37 CFR 1.143) and (ii) identification of the claims encompassing the elected invention. The election of an invention may be made with or without traverse. To reserve a right to petition, the election must be made with traverse. If the reply does not distinctly and specifically point out supposed errors in the restriction requirement, the election shall be treated as an election without traverse. Traversal must be presented at the time of election in order to be considered timely. Failure to timely traverse the requirement will result in the loss of right to petition under 37 CFR 1.144. If claims are added after the election, applicant must indicate which of these claims are readable upon the elected invention. Should applicant traverse on the ground that the inventions are not patentably distinct, applicant should submit evidence or identify such evidence now of record showing the inventions to be obvious variants or clearly admit on the record that this is the case. In either instance, if the examiner finds one of the inventions unpatentable over the prior art, the evidence or admission may be used in a rejection under 35 U.S.C. 103 or pre-AIA 35 U.S.C. 103(a) of the other invention. This application contains claims directed to the following patentably distinct species various bismuth compounds with the recited (organic) ligands. The species are independent or distinct because they have different functionality (due to their different ligands) and utility. The search of the entire group of bismuth compounds would represent a serious burden. In addition, these species are not obvious variants of each other based on the current record. Applicant is required under 35 U.S.C. 121 to elect a single disclosed species, or a single grouping of patentably indistinct species, for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable. Currently, each of claims 1,16 and 23 are generic. There is a serious search and/or examination burden for the patentably distinct species as set forth above because at least the following reason(s) apply: The bismuth organometallic compounds have different functionality (due to their different ligands) and utility. The search of the entire group of bismuth organometallic compounds would represent a serious burden, noting that claim 13 alone recites 192 individual bismuth organometallic compounds. In addition, these species are not obvious variants of each other based on the current record. The applicant is directed to choose a single compound as a point for the search and examination to begin as well as elect either (the combination of groups I and II) or group III. The applicant should also identify which claims embrace the elected compound. Applicant is advised that the reply to this requirement to be complete must include (i) an election of a species to be examined even though the requirement may be traversed (37 CFR 1.143) and (ii) identification of the claims encompassing the elected species or grouping of patentably indistinct species, including any claims subsequently added. An argument that a claim is allowable or that all claims are generic is considered nonresponsive unless accompanied by an election. The election may be made with or without traverse. To preserve a right to petition, the election must be made with traverse. If the reply does not distinctly and specifically point out supposed errors in the election of species requirement, the election shall be treated as an election without traverse. Traversal must be presented at the time of election in order to be considered timely. Failure to timely traverse the requirement will result in the loss of right to petition under 37 CFR 1.144. If claims are added after the election, applicant must indicate which of these claims are readable on the elected species or grouping of patentably indistinct species. Should applicant traverse on the ground that the species, or groupings of patentably indistinct species from which election is required, are not patentably distinct, applicant should submit evidence or identify such evidence now of record showing them to be obvious variants or clearly admit on the record that this is the case. In either instance, if the examiner finds one of the species unpatentable over the prior art, the evidence or admission may be used in a rejection under 35 U.S.C. 103 or pre-AIA 35 U.S.C. 103(a) of the other species. Upon the allowance of a generic claim, applicant will be entitled to consideration of claims to additional species which depend from or otherwise require all the limitations of an allowable generic claim as provided by 37 CFR 1.141. A telephone call was made to Kelsey Skoje (77205) on December 1, 2025 to request an oral election to the above restriction requirement, but did not result in an election being made. The examiner had considered allowing the case to return to the general pendency reduction docket, but decided to begin the prosecution. Applicant is reminded that upon the cancelation of claims to a non-elected invention, the inventorship must be corrected in compliance with 37 CFR 1.48(a) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. A request to correct inventorship under 37 CFR 1.48(a) must be accompanied by an application data sheet in accordance with 37 CFR 1.76 that identifies each inventor by his or her legal name and by the processing fee required under 37 CFR 1.17(i). The examiner has required restriction between product or apparatus claims and process claims. Where applicant elects claims directed to the product/apparatus, and all product/apparatus claims are subsequently found allowable, withdrawn process claims that include all the limitations of the allowable product/apparatus claims should be considered for rejoinder. All claims directed to a nonelected process invention must include all the limitations of an allowable product/apparatus claim for that process invention to be rejoined. In the event of rejoinder, the requirement for restriction between the product/apparatus claims and the rejoined process claims will be withdrawn, and the rejoined process claims will be fully examined for patentability in accordance with 37 CFR 1.104. Thus, to be allowable, the rejoined claims must meet all criteria for patentability including the requirements of 35 U.S.C. 101, 102, 103 and 112. Until all claims to the elected product/apparatus are found allowable, an otherwise proper restriction requirement between product/apparatus claims and process claims may be maintained. Withdrawn process claims that are not commensurate in scope with an allowable product/apparatus claim will not be rejoined. See MPEP § 821.04. Additionally, in order for rejoinder to occur, applicant is advised that the process claims should be amended during prosecution to require the limitations of the product/apparatus claims. Failure to do so may result in no rejoinder. Further, note that the prohibition against double patenting rejections of 35 U.S.C. 121 does not apply where the restriction requirement is withdrawn by the examiner before the patent issues. See MPEP § 804.01. Applicant's election with traverse of groups I and II with the species elected being 2,4-dimethyl-1,3,2,4-dioxabismetane in the reply filed on 02/06/2026 is acknowledged. The traversal is on the ground(s) that the claims are in Markush format, there is no burden and that the examiner has not articulated why the bismuth compounds are not patentably distinct This is not found persuasive because there are hundreds of specific compounds recited in the claims which constitutes a significant burden. An election of species is clearly permitted under Markush practice as set forth in MPEP 803.02. It is not clear what single structural similarity the members of the asserted Markush group share and the applicant has not discussed this in their response, so it is not clear if this is properly a Markush group. The examiner can require an election of “a single species” as discussed at 803.02(III). The examiner holds that each is distinct and other than pointing to this, the applicant has not refuted that point. If the applicant wishes to asserts that they are obvious variants, they should do so clearly in the written record. The requirement is still deemed proper and is therefore made FINAL. Claims 23-25 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on 02/05/2026. Claims 1,2 (formula III), 3, claim 4 (formula d),claims 5-22 embrace the elected compound. Claims 23-25 are directed to the non-elected process of use which was elected without traverse. 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 1-22 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Machida JP H11199233 Machida JP H11199233 (machine translation attached) teaches dissolving as trialkylbismuth solution and vaporizing the trialkylbismuth in the presence of oxygen to form a bismuth oxide film [0029]. Example 1 vaporizes trimethylbismuth from a solution using toluene as the solvent without an explosion [0032]. In example 4, trimethylbismuth was vaporized and allowed to come into contact with oxygen in a furnace contusing a silicon substrate. The heating at 165-260 degrees C yielded a bismuth oxide film on the substrate [0038-0039]. Examples 5 and 6 are similar, but use dioxane as the solvent and yielded a bismuth oxide film [0040-0043]. Example 7 is similar, but uses 1-2-diethoxyane as the solvent [0044-0045]. Examples 8-10 are similar to example 1 and yield a bismuth oxide film [0046-0051]. Example 12 combined trimethylbismuth and tetraisopropyl titanium, heat these in the presence of oxygen to form a bismuth titanate film [0054-0055] Example 13 forms a strontium calcium bismuth copper oxide [0056-0058]. Example 14 forms a film of strontium tantalum bismuth oxide [0059-0061]. In other Embodiments, instead of trimethylbismuth, triethylbismuth, tri-n-propylbismuth, triiso-propylbismuth, tri-n-butylbismuth, triiso-butylbismuth, trisec- The same operation was performed using butyl bismuth and trivinyl bismuth. As a result, a similar film was formed [0062]. The position of the examiner is that the reaction between the trimethylbismuth and oxygen to yield the bismuth oxide films of the cited examiner proceeds as follows. First reaction: Two Bi(CH3)3 + O yields (CH3)2Bi-O-Bi(CH3)2 Second reactions: (CH3)2Bi-O-Bi(CH3)2 + O yields PNG media_image1.png 92 71 media_image1.png Greyscale (CH3)2Bi-O-Bi(CH3)2 + O + Bi(CH3)3 Yields ((CH3)2BiO)2-Bi(CH3) Third reactions includes : PNG media_image2.png 111 144 media_image2.png Greyscale + two O +two Bi(CH3)3 yields bismuth oxide As well as the reactions ((CH3)2BiO)2-Bi(CH3) + O , ((CH3)2BiO)2-Bi(CH3) + O + Bi(CH3)3 and ((CH3)2BiO)2-Bi(CH3) + two O + Bi(CH3)3 and ((CH3)2BiO)2-Bi(CH3) + two O + two Bi(CH3)3 which form other precursors which further react to form the bismuth oxide coating. With respect to claims 1-15, the position of the examiner is that the elected compound is inherently formed as an intermediate in the CVD process reacting trimethylbismuth and oxygen resulting in the formation of a bismuth oxide film on the substrate and the claims are anticipated. With respect to claims 16, the position of the examiner is that the elected compound is inherently formed as an intermediate in the CVD process reacting trimethylbismuth and oxygen resulting in the formation of a bismuth oxide film on the substrate and the claimed are anticipated as the organometallic compound is provided. With respect to claims 17 and 20-22, the position of the examiner is that the elected compound is inherently formed as an intermediate in the CVD process reacting trimethylbismuth and oxygen resulting in the formation of a bismuth oxide film on the substrate and the claims are anticipated. The hardmask claims rejected under this heading do not require anything beyond the compound. With respect to claims 17 and 19-22, the position of the examiner is that the elected compound is inherently formed as an intermediate in the CVD process reacting trimethylbismuth and oxygen resulting in the formation of a bismuth oxide film on the substrate and the solvent is also present in the gas phase. The claims are anticipated. The hardmask claims rejected under this heading do not require anything beyond the compound. With respect to claims 17 and 19-22, the position of the examiner is that the elected compound is inherently formed as an intermediate in the CVD process reacting trimethylbismuth and oxygen resulting in the formation of a bismuth oxide film on the substrate and the nitrogen is also present in the gas phase as a diluent/solvent. The claims are anticipated. The hardmask claims rejected under this heading do not require anything beyond the compound. With respect to claims 17,18 and 20-22, the position of the examiner is that the elected compound is inherently formed as an intermediate in the CVD process reacting trimethylbismuth and oxygen resulting in the formation of a bismuth oxide film on the substrate and the oxygen is also present in the gas phase as a reactant. The claims are anticipated. The hardmask claims rejected under this heading do not require anything beyond the compound. The position of the examiner is that the language in claim 17 “the organometallic compound comprising” embraces the presence of other bismuth containing organometallic component and has interpreted claim 18 as including other organometallic compounds in the recited 5-95, 10-90 and 20-80 wt% With respect to claims 17-22, the position of the examiner is that the elected compound is inherently formed as an intermediate in the CVD process reacting trimethylbismuth and oxygen resulting in the formation of a bismuth oxide film on the substrate and the oxygen is also present in the gas phase as a reactant and substrate and the solvent is also present in the gas phase. The claims are anticipated. The hardmask claims rejected under this heading do not require anything beyond the compound. The examiner also asserts that the bismuth oxide is not a complete oxide and that at some of the elected compound is present in the coated film is present in the coated film. Claims 1-22 are rejected under 35 U.S.C. 103 as being unpatentable over Machida JP H11199233, in view of Xue et al. WO 2021146138. Xue et al. WO 2021146138 teaches embodiments where the precursor includes bismuth, such as in BiR.sub.3, wherein each R is, independently, halo, optionally substituted C.sub.1-12 alkyl, mono-C.sub.1-12 alkylamino (e.g., -NR.sup.1H), di-C.sub.1-12 alkylamino (e.g., -NR.sup.1R.sup.2), optionally substituted aryl, optionally substituted bis(trialkylsilyl)amino (e.g., -N(SiR.sup.1R.sup.2R.sup.3).sub.2), or a diketonate (e.g., -OC(R.sup.4)-Ak- (R.sup.5)CO-). In particular embodiments, each R.sup.1, R.sup.2, and R.sup.3 is, independently, C.sub.1-12 alkyl (e.g., methyl, ethyl, isopropyl, /-butyl, or neopentyl); and each R.sup.4 and R.sup.5 is, independently, H or optionally substituted C.sub.1-12 alkyl (e.g., methyl, ethyl, isopropyl, /-butyl, or neopentyl). Nonlimiting bismuth precursors include BiCb, BiMes, BiPhs, Bi(NMe.sub.2).sub.3, Bi[N(SiMe3)2]3, and Bi(thd)3, in which thd is 2,2,6,6-tetramethyl-3,5-heptanedionate [0165]. The processes herein can be used to deposit a thin metal oxide or metal by ALD or CVD. Examples include tin oxide (SnO.sub.x), bismuth oxide (BiO.sub.x), and Te [0211] Processes herein can be used to achieve a surface modification. In some iterations, a vapor of the precursor may be passed over the wafer. The wafer may be heated to provide thermal energy for the reaction to proceed. In some iterations, the heating can be between about 50°C to about 250°C. In some cases, pulses of the precursor may be used, separated by pump and/or purging steps. For instance, a first precursor may be pulsed between pulses of a second precursor pulses resulting in ALD or ALD-like growth. In other cases, both precursors may be flowed at the same time. Examples of elements useful for surface modification include I, F, Sn, Bi, Sb, Te, and oxides or alloys of these compounds [0210] Suitable vapor deposition processes include chemical vapor deposition (CVD), atomic layer deposition (ALD), plasma-enhanced chemical vapor deposition (PECVD), or plasma-enhanced atomic layer deposition (PEALD) [0184]. Machida JP H11199233does not fairly teach the recited compound being coated on the substrate surface as a major component of the coating. It would have been obvious to modify the process of forming the bismuth oxide coating of Machida JP H11199233 by using atomic layer deposition (ALD) in place of the CVD process and providing the trimethylbismuth reactant first as taught in Xue et al. WO 2021146138 with a reasonable expectation of forming a bismuth oxide layer based upon the disclosure of ALD as an alternative to CVD in Xue et al. WO 2021146138 at [0184,0211] and the disclosure of precursors which embrace the trimethylbismuth in Xue et al. WO 2021146138 at [0165]. The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Ermert et al. 20230126125 teaches tin compounds useful in resists including those bounded by formula (I) PNG media_image3.png 175 349 media_image3.png Greyscale and formula IV PNG media_image4.png 195 195 media_image4.png Greyscale and VI PNG media_image5.png 199 229 media_image5.png Greyscale [0018] Daiss et al. WO 2011051108 (machine translation attached) teaches siloxanes of formula IV on page 18. Rosthauser et al. 6020283 teaches tin compounds PNG media_image6.png 81 206 media_image6.png Greyscale Tokitoh, “New aspects in the chemistry of low-coordinated inter-element compounds as heavier group 15 elements. J. Organometallic Chem., Vol. 611 pp 217-227 (2000) teaches cyclic bismuth compounds on pages 220 and 223. PNG media_image7.png 148 128 media_image7.png Greyscale PNG media_image8.png 184 351 media_image8.png Greyscale Suzuki et al. “Organobismuth chemistry”, Elevier 2001 (637 pages) exemplifies on page 368 compounds: PNG media_image9.png 359 218 media_image9.png Greyscale OK et al., KR 20130026183 (machine translation attached) teaches Bi-O polymers 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, Mark F 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. MARTIN J. ANGEBRANNDT Primary Examiner Art Unit 1737 /MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 February 27, 2026
Read full office action

Prosecution Timeline

May 18, 2023
Application Filed
Feb 27, 2026
Non-Final Rejection — §102, §103, §DP (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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1-2
Expected OA Rounds
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Grant Probability
90%
With Interview (+34.5%)
3y 3m
Median Time to Grant
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