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 .
DETAILED ACTION
Claims 1-8 and 10-37 of R.E. Jilek et.al. US 17/682,586 (02/28/2022) are pending. Claims 5, 7-8, 11 and 17-35 are withdrawn as drawn to non-elected Groups or not read on the elected species. Applicant added new claims 36-37 in the reply filed on 08/06/2025 and canceled claim 9 in the reply filed on 12/17/2025, which resulted in the elected Group (I) drawn to claims 1-8, 10-16 and 36-37. Claims 1-4, 6, 10 and 12-16, 36-37 are under examination on merits and are rejected.
Withdrawal of Office Action Finality
A request for continued examination of US 17/682,586 under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 12/17/2025 has been entered.
Election/Restrictions
Applicant elected Group (I) drawn to now claims 1-8,10-16 and 36-37 , without traverse, in the Reply to Restriction Requirement filed on 04/15/2025. Claims 17-35 drawn to non-elected Groups (II)-(III) are withdrawn from consideration pursuant to 37 CFR 1.142(b). The restriction requirement is maintained as FINAL.
Pursuant to the election of species requirement, Applicant elected, without traverse, nonadeutero-tert-butyltin tris(tert-butoxide) as the species for the general RSnL3, in the reply filed on 04/15/2025, for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable.
PNG
media_image1.png
200
400
media_image1.png
Greyscale
The elected species was searched and determined to be unpatentable as discussed in the 103 rejection below. The searching has been extended another compound as mentioned in the 103 rejection. The provisional species election requirement is in effect and claims 5, 7-8, 11 are withdrawn as not reading on the elected species.
Withdrawal Claim Rejections - 35 USC § 102
Rejection of claims 1-3 under 35 U.S.C. 102(a)(1) as being anticipated by the CAS abstract RN 76178-63-7 (1984) is withdrawn in view of claim amendment that is the instant claim 1 has been amended by Applicant further limitation of the ligand L.
Rejection of claims 1-3, 13-15 and 36-37 under 35 U.S.C. 102(a)(1) as being anticipated by E. Kaletová, et al. 137 Journal of the American Chemical Society 12086-12099 (2015)(“Kaletová”) is withdrawn in view of claim amendment that is the instant claim 1 has been amended by Applicant further limitation of the ligand L.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See, MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01. It is also appropriate to look to how the claim term is used in the prior art, which includes prior art patents, published applications, trade publications, and dictionaries. MPEP § 2111.01 (III).
Interpretation of the term “hydrolysable ligand”
Independent claim 1 recites the term “hydrolysable ligand” in the following context:
1. An organotin compound represented by the formula RSnL3, wherein R is a deuterated hydrocarbyl group and L is a hydrolysable ligand.
The specification provides the following discussion with respect to the claimed “hydrolysable ligand”:
As described herein, the hydrolysable ligand is a ligand that promotes reaction of water with an organotin molecule to produce an organotin oxide hydroxide composition illustrated by the following reaction:
RSnL3+2H2O-- RSnOOH + 3 HL. (1).
. . .
Hydrolysis of the RSnL3 composition above generally yields hydroxide and oxide rich products where two or more RSn moieties are condensed to form Sn-O and Sn-OH bonds
Specification at page 6, line 1-9.
Therefore, consistent with the specification, the term “hydrolysable ligand” is broadly and reasonably interpreted as any ligand binding to the Sn atom of an organotin atom and the ligand can be hydrolyzed with water to from an organotin oxide hydroxide; wherein the organotin oxide hydroxide comprises both at least one Sn-O bond and at least one Sn-OH.
Interpretation of the term “a natural abundance of deuterium”
The specification defines that “The natural abundance of deuterium is about 0.016% of hydrogen”. Specification at page 18, line 21. Therefore, the term of “a natural abundance of deuterium” is interpreted as defined by the specification.
Maintained 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.
Claims 1-4, 6, 10-16, 36-37 and the elected species are rejected under 35 USC § 103 Rejection over S. Meyers, et al, US10228618B2(2019)(“Meyers”) in view of X-C.C. Li, et al, US2002076576A1 (2002)(“Li”) for the same reason as given in the previous Office action and is repeated below.
S. Meyers, et al, US 10228618B2 (2019) (“Meyers”)
Meyers teaches a coated substrate comprising a substrate with a surface and a coating on the surface comprising an organometallic composition represented by the y (RzSnO(2−(z/2)−(w/2))(OH)w.zMO((m/2)−1/2)(OH)l where 0<z≤2, 0<(z+w)≤4, m=formal valence of Mm+, 0≤l≤m, y/z=(0.05 to 0.6), and M=M′ or Sn, where M′ is a non-tin metal of groups 2-16 of the periodic table, and R is hydrocarbyl groups with 1-31 carbon atoms.
Meyers at col. at col. 3, line 11-18, emphasis added..
Meyers teaches that the coating can be formed through the following method:
the method comprising inputting into a deposition chamber closed from the ambient atmosphere separately a first precursor vapor comprising a compound RnSnX4−n where n=1 or 2, wherein R is a hydrocarbyl group with 1-31 carbon atoms, and X is a hydrolysable or oxidizable ligand and a second precursor vapor comprising an oxygen containing compound capable of hydrolyzing or oxidizing the first precursor vapor under conditions in the deposition chamber to form a hydrolyzed or oxidized composition.
Meyers at col. 2, line 67 to col.3, line 10, emphasis added.
Meyers teaches that the coated substrate can be used as an inorganic semiconductor layer and a radiation sensitive coating material. Meyers at col. 3, line 23-25.
Meyers teaches examples of the precursor RnSnX4−n such as the compound of tBuSn(OtBu)3 and compound of tBuSn(NEt2)3
PNG
media_image2.png
200
400
media_image2.png
Greyscale
Meyers at col. 18, Table 1, row 3 and col 19, line 24-25.
PNG
media_image3.png
436
472
media_image3.png
Greyscale
Meyers at col. 18, Table 1, row 1 and col 19, line 19.
Therefore, Meyers fairly teaches one ordinary skilled artisan that tBuSn(OtBu)3 and tBuSn(NEt2)3 are alternative as precursors.
Meyers also teaches a composition comprising 3.0 mmol of tBuSn(NEt2)3 and 15 ml of 4-methyl-2-pentanol for coating. Meyers col. 26, Example 1, line 59-65.
Meyers further teaches that:
Tert-butyltin oxide hydroxide photoresist films were deposited from precursor coating solutions from Example 4 prepared from tBuSn(NEt2)3 and, for some coating solutions, Sn(NMe2)4 or Sn(OtBu)4, and then exposed with EUV radiation. Thin films for EUV contrast curves were deposited on silicon wafers (100-mm diameter) with a native oxide surface.
Meyers col. 30, Example 5, line 5-11, emphasis added.
Difference between Meyers and the Claims
The Meyers differs from the instant claims only in that Meyers does not teach the tBu group in tBuSn(NEt2)3 or tBuSn(OtBu)3 is deuterated and the deuterium enrichment greater than natural abundance.
X-C.C. Li, et al, US2002076576A1 (2002)(“Li”)
Li teaches that:
Deuterium is a non-radiative isotope of hydrogen, which is sometimes called heavy hydrogen due to its doubled atomic mass. The difference between hydrogen and deuterium has fairly small chemical effects; however, there are important physical effects because of the mass difference between the isotopes. The heavier isotope, deuterium, lies lower in the potential well, and hence has a lower zero-point energy and vibration frequency, and smaller vibration amplitude than hydrogen. Because of the asymmetry of the potential well, bond lengths and bond angles involving deuterium are different than those involving hydrogen. The observed smaller amplitude of the C-D stretching and bending motion, relative to C-H, should be best accounted for with a smaller van der Waals radius for D than for H. The weak vibronic coupling in the deuterated system has been used to theoretically predict higher fluorescence quantum yield [A. L. Burin and M. A. Ratner, J. Chem. Phys., 1998, 109, 6092]. Spectroscopic studies indicate that deuterated phenanthrene has a smaller non-radiative triplet rate constant than its aromatic molecule [S. M. Ramasamy, R. j. Hurtubise, Appl. Spectroscopy, 1996, 50(9), 1140]. Deuterium is also found to act as an apparent electron-donating inductive substituent relative to hydrogen. The isotope effects may be applied in the design of new luminescent materials with enhanced charge-injection ability. Additionally, it is know that the C-D bond is shorter than the C-H as a result of the anharmonicity of the bond stretching potential. [M. L. Allinger and H. L. Flanagan, j. Computational Chem. 1983, 4(3), 399]. This means the carbon-deuterium chemical bond is stronger, more stable, and reacts more slowly than the carbon-hydrogen chemical bond, so that the deuterated organic system has better thermal stability, and longer lifetime in optoelectronic devices.
Li at page 1, [008] to page 2, [0009], emphasis added.
Obviousness Rational of Claims 1-4, 6, 9-10 and 13-16, 36-37
It would have been prima facie obvious for one skilled artisan to arrive at the instantly claimed invention based on the teachings from Meyers and Li with a reasonable expectation of success before the effective filing date of the claimed invention.
Obviousness of a claimed compound can be supported where there is motivation to substitute particular chemical moieties in a prior art compound for others so as to arrive at a claimed compound. MPEP § 2143(I)(B). For example, in the pharmaceutical arts, the rational is stated as motivation to select a known compound and also motivation to structurally modify the selected compound in a particular way to achieve a claimed compound. MPEP § 2143(I)(B) (see for example, MPEP § 2143(I)(B) Example 9, citing Eisai Co. Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 87 USPQ2d 1452 (Fed. Cir. 2008).
One skilled artisan seeking tert-butyltin oxide hydroxide containing photoresist films is motivated to modify the Meyers precursor tBuSn(NEt2)3 by replacing all the hydrogen atoms in the tBu group by deuterium atoms as indicated below and use it as a precursor to deposit a film as taught by Meyers.
PNG
media_image4.png
394
1113
media_image4.png
Greyscale
The proposed compound maps the formula RSnL3 in claims 1-3, 6, 8-10; and 36-37 as:
R is -C(CD3)3 which is a perdeuterated branched alky,
L is –N(CH2CH3)2 which is a hydrolysable ligand.
It meets each and every limitation of claims 1-3, 6, 9-10 and 36-37, therefore, claims 1-3, 6, 9-10 and 36-37 are obvious.
One skilled artisan has a motivation to do so with a reasonable expectation of success because:
(i). Meyers teaches that tBuSn(NEt2)3 can be used as a precursor to deposit tert-butyltin oxide hydroxide containing photoresist films, and
(ii). Li teaches that the carbon-deuterium chemical bond is stronger, more stable, and reacts more slowly than the carbon-hydrogen chemical bond, so that the deuterated organic system has better thermal stability, and longer lifetime in optoelectronic devices.
Claims 13, 15-16 are obvious because one ordinary skilled artisan is motivated to prepare a composition comprising 3.0 mmol of (tBu-d9)Sn(NEt2)3 and 15 ml of 4-methyl-2-pentanol (3 mmol/15 ml=0.33 M) as taught by Meyers for coating, thereby arrive at composition meeting each and every limitation of claims 13, 15-16, therefore, claims 13, 15-16 are obvious.
Claim 14 is also obvious because one ordinary skilled artisan is also motivated to include a second precursor such as Sn(NMe2)4 or Sn(OtBu)4 into the solution as taught by Meyers.
Obviousness Rational of Claim 12 and the elected Species
Claim 12 and the elected species are obvious because one ordinary skilled artisan seeking tert-butyltin oxide hydroxide containing photoresist films is also motivated to modify the Meyers precursor tBuSn(OtBu)3 by replacing all the hydrogen in the tBu group by Deuterium as indicated below, thus arrive at the elected species which is the first claimed species in claim 12, and use it as a precursor to deposit a film as taught by Meyers
.
PNG
media_image5.png
394
1113
media_image5.png
Greyscale
One ordinary skilled artisan is motivated to do so with a reasonable expectation of success because Meyers teaches that tBuSn(OtBu)3 is an alternative of (tBu-d9)Sn(NEt2)3 as the precursor to deposit photoresist films.
Applicant’s Argument
Applicant argues on the motivation for the proposed modification because compounds disclosed by Li and Meyers have different applications. Response to the Claim Rejections under 35 U.S.C. 103 over Meyers and Li, page 10-12, Remarks submitted on 12/17/2025.
These arguments have been fully considered but not persuasive. While the compounds disclosed by Li and Meyers have different applications, however, thermal stability of a compound is not change with its different applications. Given Li teaches that carbon-deuterium chemical bond is stronger, more stable than carbon-hydrogen chemical bond because C-D bond is shorter than the C-H; and Meyers teaches tBuSn(NEt2)3 and/or tBuSn(OtBu)3 can be used as a precursor to form tert-butyltin oxide hydroxide containing photoresist films, one ordinary skill is motivated to replacing all the hydrogen atoms in the tBu group by deuterium atoms as proposed in the previous Office action and above as the replacement can enhance the thermal stability of tert-butyltin oxide hydroxide in the film and extend lifetime of the film.
Maintained 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).
Double Patenting Rejection over US 11498934B2 (2022)
Claim 1-4, 6, 9-10, 12-13,15 and 36-37 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 10 of U.S.11498934B2 in view of X-C.C. Li, et al, US2002076576A1 (2002)(“Li”) is maintained for the same reason as given in the previous Office action and is repeated below.
Conflicting Claims
Conflicting claim 1 claims a composition comprising a solvent and monoalkyl tin trialkoxide (RSn(OR′)3) or monoalkyl tin triamide (RSn(NR′2)3) with a tin concentration from about 0.005M to about 0.5M dissolved in the solvent.
Conflicting claim 4 claims further claims that the composition of claim 1 comprising a monoalkyl tin trialkoxide.
Conflicting claim 10 claims further claims that the composition of claim 1 comprising a monoalkyl tin trialkoxide, R comprising methyl (CH3-), ethyl (CH3CH2-), isopropyl (CH3CH3HC-), t-butyl ((CH3)3C-), t-amyl (CH3CH2(CH3)2C-), sec-butyl (CH3(CH3CH2)CH-), neopentyl (CH3)3CCH2-), or a combination thereof, and R′ comprising a methyl group, ethyl group, isopropyl group, t-butyl group or a combination thereof.
One ordinary skill is motivated to perform the combination of the conflicting claims 1,4 and 10 by election of t-butyl as both R and R’, thus arrive at a solution comprising tBuSn(OtBu)3 with a tin concentration from about 0.005M to about 0.5M dissolved in the solvent. The rational supporting the election is obvious to try. MPEP 2143-(I)(E).
A reference specification may be reviewed to construe the conflicting claims. MPEP § 804(II)(B)(1). Further, those portions of the specification which provide support for the conflicting claims may also be examined and considered when addressing the issue of whether a claim in the application defines an obvious variation of an invention claimed in the reference patent or application. MPEP § 804(II)(B)(1) (citing In re Vogel, 422 F.2d 438, 441-42, 164 USPQ 619, 622 (CCPA 1970)). The court in Vogel recognized ‘that it is most difficult, if not meaningless, to try to say what is or is not an obvious variation of a claim,’ but that one can judge whether or not the invention claimed in an application is an obvious variation of an embodiment disclosed in the patent or application which provides support for the claim. MPEP § 804(II)(B)(1). In this regard, it is also proper to look at the disclosed utility in the reference disclosure to determine the overall question of obviousness in a nonstatutory double patenting context. MPEP § 804(II)(B)(1) (citing AbbVie Inc. v. Kennedy Institute of Rheumatology Trust, 764 F.3d 1366, 112 USPQ2d 1001 (Fed. Cir. 2014); Sun Pharm. Indus., Ltd. v. Eli Lilly & Co., 611 F.3d 1381, 95 USPQ2d 1797 (Fed. Cir. 2010); Pfizer, Inc. v. Teva Pharm. USA, Inc., 518 F.3d 1353, 86 USPQ2d 1001 (Fed. Cir. 2008); Geneva Pharmaceuticals Inc. v. GlaxoSmithKline PLC, 349 F3d 1373, 1385-86, 68 USPQ2d 1865, 1875 (Fed. Cir. 2003)). Herein, the conflicting specification discloses that composition claimed by the conflicting claims can be used as photoresists for EUV lithography. Specification at col. 1, 11-16. Therefore, the conflicting application discloses the utility of the claimed composition.
Difference between the combination of conflicting claims 1,4, 10 and the instant Claims
The difference between the combination of conflicting claims 1,4, 10 and the elected species only in that the conflicting claims do not claim the tBu group in tBuSn(OtBu)3 is deuterated or perdeuterated.
X-C.C. Li, et al, US2002076576A1 (2002)(“Li”).
Li has been discussed above for the 103 rejection.
Claim 1-4, 6, 9-10, 12-13,15 and 36-37 are Obvious
Claim 1-4, 6, 9-10, 12-13,15 and 36-37 are obvious because one ordinary skilled artisan seeking photoresists material for EUV lithography is motivated to modify the tBuSn(OtBu)3 taught by the combination of the conflicting claims 1,4, 10 by replacing all the hydrogen in the tBu group by Deuterium as indicated below, thus arrive at the elected species which is the first claimed species in claim 12 for the same reason as given in the 103 rejection above.
PNG
media_image5.png
394
1113
media_image5.png
Greyscale
The proposed compound meets each and every limitation of claims 1-4, 6, 9-10, 12 and 36-37, therefore, claims 1-4, 6, 9-10, 12 and 36-37 are obvious.
Claims 13, 15 and 16 are obvious because one ordinary skilled artisan seeking photoresists material for EUV lithography is also motivated to preparation a composition comprising a solvent and the proposed compound with a concentration from about 0.005M to about 0.5M dissolved in the solvent as claimed by the conflicting claim.
Terminal Disclaimer
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
Applicant’s Argument
Applicant argues on the ground that the instant claims and the claims of the '934 Patent are patentably distinct from one another because none of the claims of the '934 Patent are directed to deuterated organotin products. Response to the Non-Statutory Double Patenting over the '934 Patent, page 12-13, Remarks submitted on 12/17/2025.
These argument is not persuasive. As mentioned in the previous Office action that a reference specification may be reviewed to construe the conflicting claims. MPEP § 804(II)(B)(1). Further, those portions of the specification which provide support for the conflicting claims may also be examined and considered when addressing the issue of whether a claim in the application defines an obvious variation of an invention claimed in the reference patent or application. MPEP § 804(II)(B)(1). Herein, while none of the claims of the '934 Patent are directed to deuterated organotin products, however, the specification the '934 Patent teaches the utility of conflicting claims claimed compound. Therefore, one ordinary kill has a motivation to modified the compounds claimed by the conflicting claims as proposed in view of the teachings from Li to arrive at the instant claimed invention.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
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, Scarlett Goon can be reached at (571)2705241. 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.
/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692