Prosecution Insights
Last updated: May 29, 2026
Application No. 18/329,976

ORGANOMETALLIC COMPOUND, RESIST COMPOSITION INCLUDING THE SAME AND PATTERN FORMING METHOD USING THE SAME

Final Rejection §102§103
Filed
Jun 06, 2023
Priority
Dec 27, 2022 — RE 10-2022-0186393
Examiner
EOFF, ANCA
Art Unit
1722
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Samsung Electronics Co., Ltd.
OA Round
2 (Final)
80%
Grant Probability
Favorable
3-4
OA Rounds
0m
Est. Remaining
91%
With Interview

Examiner Intelligence

Grants 80% — above average
80%
Career Allowance Rate
992 granted / 1241 resolved
+14.9% vs TC avg
Moderate +11% lift
Without
With
+11.3%
Interview Lift
resolved cases with interview
Typical timeline
2y 8m
Avg Prosecution
31 currently pending
Career history
1280
Total Applications
across all art units

Statute-Specific Performance

§101
0.2%
-39.8% vs TC avg
§103
84.4%
+44.4% vs TC avg
§102
7.7%
-32.3% vs TC avg
§112
5.1%
-34.9% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1241 resolved cases

Office Action

§102 §103
DETAILED ACTION The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Claims 1-20 are pending. The foreign priority application No. 10-2022-0186393 filed on December 27, 2022 has been received and it is acknowledged. Double Patenting The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969). A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b). The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13. The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer. Claims 1-7, 9, 11-14, 17, 18, and 20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 12, 15-18, and 20 of copending Application No. 18/620,240 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because both applications claim the same compounds, the same photoresist composition, and the same pattern forming method. The copending Application No. 18/620,240 claims a resist composition comprising a first organometallic compound which may be represented by the formulas: PNG media_image1.png 102 260 media_image1.png Greyscale PNG media_image2.png 100 252 media_image2.png Greyscale PNG media_image3.png 124 260 media_image3.png Greyscale PNG media_image4.png 100 254 media_image4.png Greyscale PNG media_image5.png 138 256 media_image5.png Greyscale PNG media_image6.png 92 272 media_image6.png Greyscale and PNG media_image7.png 102 264 media_image7.png Greyscale , wherein n is an integer from 1 to 4 (claims 1 and 12). The compounds above are compounds of formulas 1-1 to 1-4 in claims 1-7 and 9 of the instant application. The compounds above wherein n=2 are compounds in claim 11 of the instant application. The resist composition in claims 1 and 12 of copending Application No. 18/620,240 is equivalent to the resist composition in claim 12 of the instant application. The copending Application No. 18/620,240 further claims that the resist composition does not comprise a photoacid generator (claim 15), same as in claim 13 of the instant application. The copending Application No. 18/620,240 further claims that the resist composition does not comprise a compound having a molecular weight of 1,000 or more (claim 16), same as in claim 14 of the instant application. The copending Application No. 18/620,240 further claims a pattern forming method comprising: forming a resist film by applying the resist composition onto a substrate, exposing at least a portion of the resist film to high-energy rays to provide an exposed resist film, developing the exposed resist film using a developer (claim 17), same as in claim 17 of the instant application. The copending Application No. 18/620,240 further claims that the exposing at least a portion of resist film is performed by irradiating the resist film using at least one of deep ultraviolet (DUV) rays, extreme ultraviolet (EUV) rays, or electron beams (EBs)(claim 18), same as in claim 18 of the instant application. The copending Application No. 18/620,240 further claims that the exposed film includes an exposed portion and a non-exposed portion, and in the developing step the non-exposed portion is removed (claim 20), same as in claim 20 of the instant application. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Claims 1-7, 9, 11-14, 17, 18, and 20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 7, 15-18, and 20 of copending Application No. 18/635,761 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because both applications claim the same compounds, the same photoresist composition, and the same pattern forming method. The copending Application No. 18/635,761 claims a resist composition comprising a first organometallic compound which may be represented by the formulas: PNG media_image1.png 102 260 media_image1.png Greyscale PNG media_image2.png 100 252 media_image2.png Greyscale PNG media_image3.png 124 260 media_image3.png Greyscale PNG media_image4.png 100 254 media_image4.png Greyscale PNG media_image5.png 138 256 media_image5.png Greyscale PNG media_image6.png 92 272 media_image6.png Greyscale and PNG media_image7.png 102 264 media_image7.png Greyscale , wherein n is an integer from 1 to 4 (claims 1 and 7). The compounds above are compounds of formulas 1-1 to 1-4 in claims 1-7 and 9 of the instant application. The compounds above wherein n=2 are compounds in claim 11 of the instant application. The resist composition in claims 1 and 7 of the copending Application No. 18/635,761 is equivalent to the resist composition in claim 12 of the instant application. The copending Application No. 18/635,761 further claims that the resist composition does not comprise a photoacid generator (claim 15), same as in claim 13 of the instant application. The copending Application No. 18/635,761 further claims that the resist composition does not comprise a compound having a molecular weight of 1,000 or more (claim 16), same as in claim 14 of the instant application. The copending Application No. 18/635,761 further claims a pattern forming method comprising: forming a resist film by applying the resist composition onto a substrate, exposing at least a portion of the resist film to high-energy rays to provide an exposed resist film, developing the exposed resist film using a developer (claim 17), same as in claim 17 of the instant application, The copending Application No. 18/635,761 further claims that the exposing at least a portion of resist film is performed by irradiating the resist film using at least one of deep ultraviolet (DUV) rays, extreme ultraviolet (EUV) rays, or electron beams (EBs)(claim 18), same as in claim 18 of the instant application. The copending Application No. 18/635,761 further claims that the exposed film includes an exposed portion and a non-exposed portion, and in the developing step the non-exposed portion is removed (claim 20), same as in claim 20 of the instant application. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Claims 1-7, 9, 11-18, and 20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, 12, 16-18, and 20 of copending Application No. 18/921,412 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because both applications claim the same compounds, the same photoresist composition, and the same pattern forming method. The copending Application No. 18/921,412 claims a resist composition comprising a first organometallic compound which may be represented by the formulas: PNG media_image1.png 102 260 media_image1.png Greyscale PNG media_image2.png 100 252 media_image2.png Greyscale PNG media_image3.png 124 260 media_image3.png Greyscale PNG media_image4.png 100 254 media_image4.png Greyscale PNG media_image5.png 138 256 media_image5.png Greyscale PNG media_image6.png 92 272 media_image6.png Greyscale and PNG media_image7.png 102 264 media_image7.png Greyscale , wherein n is an integer from 1 to 4 (claims 1 and 5). The resist composition further comprises a solvent comprising an aprotic polar solvent (claims 1 and 12). The compounds above are compounds of formulas 1-1 to 1-4 in claims 1-7 and 9 of the instant application. The compounds above wherein n=2 are compounds in claim 11 of the instant application. The resist composition in claims 1, 6, and 12 of the copending Application No. 18/921,412 is equivalent to the resist composition in claims 12, 14, 15, and 16 of the instant application. The copending Application No. 18/921,412 further claims that the resist composition does not comprise a photoacid generator (claim 16), same as in claim 13 of the instant application. The copending Application No. 18/921,412 further claims a pattern forming method comprising: forming a resist film by applying the resist composition onto a substrate, exposing at least a portion of the resist film to high-energy rays to provide an exposed resist film, developing the exposed resist film using a developer (claim 17), same as in claim 17 of the instant application, The copending Application No. 18/921,412 further claims that the exposing at least a portion of resist film is performed by irradiating the resist film using at least one of deep ultraviolet (DUV) rays, extreme ultraviolet (EUV) rays, or electron beams (EBs)(claim 18), same as in claim 18 of the instant application. The copending Application No. 18/921,412 further claims that the exposed film includes an exposed portion and a non-exposed portion, and in the developing step the non-exposed portion is removed (claim 20), same as in claim 20 of the instant application. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Claim Rejections - 35 USC § 102 The following is a quotation of the appropriate paragraph of 35 U.S.C. 102 that forms 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. Claims 1, 2, 4-8, and 10 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Levashov et al. (“Lewis acid promoted direct synthesis of tetraalkynylstannates”). With regard to claim 1, Levashov et al. teach the compounds of formula: PNG media_image8.png 38 98 media_image8.png Greyscale , wherein R may be PNG media_image9.png 52 80 media_image9.png Greyscale or PNG media_image10.png 52 88 media_image10.png Greyscale (compounds (2) and (4) in Table 1, page 1871). These are compounds of formula 1-3, wherein L11-L14 are linear C2 divalent hydrocarbon groups, a11-a14=1, R11-R14 are unsubstituted C6 aryl groups, X11-X14 are a halogen atom or a nitro group, and n11-n14=1. With regard to claim 2, the compounds above are compounds of formula 1-3, wherein M11 is Sn. With regard to claim 4, the compounds above are compounds of formula 1-3, wherein R11-R14 are unsubstituted C6 aryl groups. With regard to claim 5, the compounds above are compounds of formula 1-3, wherein X11-X14 are a halogen atom or a nitro group. With regard to claims 6, 7, and 10, the compounds above are compounds of formula 1-3, wherein: *-R11-(X11)n11 is represented by the formula 2-3, *-R12-(X12)n12 is represented by the formula 2-23, *-R13-(X13)n13 is represented by the formula 2-43, *-R14-(X14)n14 is represented by the formula 2-63, X11c, X12c, X13c, and X14c are a halogen atom or a nitro group. With regard to claim 8, the compounds above are compounds of formula 1-3, wherein the sum of n11, n12, n13, and n14 is 4. Claims 1-9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zhang (CN 108864174 B). With regard to claim 1, Zhang teaches tri(o-chlorobenzyl)tin salicylate of formula: PNG media_image11.png 146 136 media_image11.png Greyscale (abstract), which is a compound of formula 1-2, wherein M11 is Sn, Y11 is O, R15 is *-(L15)a15-X15, a15=1, L15 is C=O, X15 is a cyclic monovalent hydrocarbon having a heteroatom-containing substituent, a11-a13=1, L11-L13 are linear divalent hydrocarbon groups, R11-R13 are unsubstituted C6 aryl groups, n11-n13=1, X11-X13 are halogen atoms. The examiner would like to note that par.0080 of the specification allows for X15 to be an aryl group substituted with a hydroxyl group. With regard to claim 2, the compound above is a compound of formula 1-2, wherein M11 is Sn. With regard to claim 3, the compound above is a compound of formula 1-2, wherein L11-L13 are unsubstituted C1 alkylene groups. With regard to claim 4, the compound above is a compound of formula 1-2, wherein R11-R13 are unsubstituted C6 aryl groups. With regard to claim 5, the compound above is a compound of formula 1-2, wherein X11-X13 are halogen atoms. With regard to claims 6 and 7, the compounds above are compounds of formula 1-2, wherein: *-R11-(X11)n11 is represented by the formula 2-1, *-R12-(X12)n12 is represented by the formula 2-21, *-R13-(X13)n13 is represented by the formula 2-41, X11c, X12c, and X13c are halogen atoms. With regard to claim 8, the compound above is a compound of formula 1-2, wherein the sum of n11, n12, and n13 is 3. With regard to claim 9, the compound above is a compound of formula 1-2, wherein Y11 is O. Claims 1-9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kiyoyanagi et al. (JP 04-107568). With regard to claim 1, Kiyoyanagi et al. teach the compound (19) of formula: PNG media_image12.png 102 186 media_image12.png Greyscale , wherein R1 is PNG media_image13.png 30 80 media_image13.png Greyscale , R2 is -pCl, and R3 is H (see Table on page 3). Kiyoyanagi et al. also teach the compound (30) of formula: PNG media_image12.png 102 186 media_image12.png Greyscale , wherein R1 is PNG media_image14.png 64 184 media_image14.png Greyscale , R2 is -pNO2, and R3 is H (see Table on page 3). The compound (19) is a compound of formula (1-1) wherein M11 is Sn, Y11 and Y12 are O, R15 and R16 are represented by *(L15)a15-X15, L15 is C=O, a15=1, X15 is a cyclic monovalent C6 hydrocarbon group which contains a heteroatom, L11 and L12 are linear C1 divalent hydrocarbon groups, a11=1, a12=1, R11 and R12 are unsubstituted C6 aryl groups, n11=0, and n12=0. The compound (30) is a compound of formula (1-1) wherein M11 is Sn, Y11 and Y12 are O, R15 and R16 are represented by *(L15)a15-X15, L15 is C=O, a15=1, X15 is a cyclic monovalent C6 hydrocarbon group which contains a heteroatom, L11 and L12 are single bonds, a11=1, a12=1, R11 and R12 are unsubstituted C6 aryl groups, n11=1, n12=1, X11 and X12 are hydroxyl groups. With regard to claim 2, the compounds (19) and (30) are compounds of formula (1-1) wherein M11 is Sn. With regard to claim 3, the compound (19) is a compound of formula (1-1) wherein L11 and L12 are unsubstituted C1 alkylene groups. With regard to claim 4, the compounds (19) and (30) are compounds of formula (1-1) wherein R11 and R12 are unsubstituted C6 aryl groups. With regard to claim 5, the compound (30) is a compound of formula (1-1) wherein X11 and X12 are hydroxyl groups. With regard to claims 6 and 7, the compound (30) is a compound of formula (1-1) wherein *-R11-(X11)n11 is represented by the formula 2-3 and *-R12-(X12)n12 is represented by the formula 2-23, wherein X11c and X12c are hydroxyl groups. With regard to claim 8, the compound (30) is a compound of formula (1-1) wherein the sum of n11 and n12 is 2. With regard to claim 9, the compound (19) is a compound of formula (1-1) wherein Y11 and Y12 are O. Allowable Subject Matter Claim 19 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. Response to Arguments Applicant’s arguments with respect to claims 1-20 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument. The examiner would like to note that: -the objection to the disclosure is withdrawn after the applicant’s amendments to par.0009 and par.0050; -the objections to claims 1-20 are withdrawn after the applicant’s amendments to claims 1 and 5; -the rejection of claims 1 and 3-8 under 35 U.S.C. 102(a)(1) as being anticipated by Toida et al. (EP 3 451 059 A1) is withdrawn after the applicant’s amendment to claim 1; -the rejection of claims 1-3, 5, 8-10, 12-15, and 17-20 under 35 U.S.C. 102(a)(1) as being anticipated by Soo et al. (KR 20210128796A, with machine translation made of record on January 16, 2026) is withdrawn after the applicant’s amendment to claim 1; -the rejection of claims 1-6 under 35 U.S.C. 102(a)(1) as being anticipated by Dolle et al. (US Patent 3,313,731) is withdrawn after the applicant’s amendment to claim 1; and -the rejection of claim 16 under 35 U.S.C. 103 as being unpatentable over Soo et al. (KR 20210128796A, with machine translation made of record on January 16, 2026) is withdrawn after the applicant’s amendment to claim 1. However, new grounds of rejection for claims 1-18 and 20 are shown in paragraphs 4-11 above. Conclusion The prior art made of record and not relied upon is considered pertinent to applicant's disclosure: Tan et al. (“Syntheses, Structures and Anticancer Activities of Two Tri(o-halobenzyl)tin Substituted Benzoates”) teach tri(o-chlorobenzyl)tin 2,4,6-trimethylbenzoate and tri(o-bromobenzyl)tin salicylate (abstract). Tri(o-chlorobenzyl)tin 2,4,6-trimethylbenzoate is represented by the formula: PNG media_image15.png 224 308 media_image15.png Greyscale , and tri(o-bromobenzyl)tin salicylate is represented by the formula: PNG media_image16.png 226 258 media_image16.png Greyscale . Kuang et al. (“Synthesis and Crystal Structure of Tetra(o-cyanobenzyl)tin”) teach tetra(o-cyanobenzyl)tin of formula: PNG media_image17.png 236 258 media_image17.png Greyscale . Applicant's amendment necessitated the new grounds 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 ANCA EOFF whose telephone number is (571)272-9810. The examiner can normally be reached Mon-Fri 10am-6:30pm. 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. /ANCA EOFF/ Primary Examiner, Art Unit 1722
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Prosecution Timeline

Show 2 earlier events
Feb 15, 2026
Interview Requested
Feb 24, 2026
Examiner Interview Summary
Feb 24, 2026
Applicant Interview (Telephonic)
Apr 08, 2026
Response Filed
Apr 23, 2026
Final Rejection mailed — §102, §103
May 06, 2026
Interview Requested
May 12, 2026
Examiner Interview Summary
May 12, 2026
Applicant Interview (Telephonic)

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Prosecution Projections

3-4
Expected OA Rounds
80%
Grant Probability
91%
With Interview (+11.3%)
2y 8m (~0m remaining)
Median Time to Grant
Moderate
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