CTNF 18/006,574 CTNF 94935 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Priority 02-27 AIA Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in parent Application No. EP20187601.8 , filed on 07/24/2020 . Information Disclosure Statement The information disclosure statements (IDSs) submitted on 01/23/2023, 07/26/2024, and 11/06/2024 were filed after the mailing date of the instant application on 01/23/2023. The submissions are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner. Election/Restrictions In a requirement for unity of invention dated 03/06/2026, Applicant was required to choose from: Group I, claims 16-22 and 24-32, drawn to an organic molecule of Formula I and a device comprising the molecule, and Group II, claim 23, drawn to a method of producing an organic molecule of Formula I from a specific reagent. Applicant’s election with traverse of Group I in the reply filed on 03/25/2026 is acknowledged. The traversal is on the grounds that (1) the patent statutes authorize, but do not require, the USPTO to restrict an application to one invention if two or more independent and distinct inventions are claimed in one application and (2) that in view of the related fields of the inventions, and in view of the expense imposed upon Applicant, Applicant believes the requirement for unity of invention should be withdrawn. This is not found persuasive because Examiner believes a serious search burden is present (MPEP 808.02). The claimed inventions require at least two different fields of search and belong in two different art classifications (a synthetic method as opposed to a product and an apparatus comprising the product). Claim 23 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Group I, drawn to claims 16-22 and 24-32, is examined herein. Response to Amendment In the preliminary amendment filed 01/23/2023, the claims, specification, and abstract were amended. These amendments are hereby entered. Claims 1-15 were originally filed. Claims 16-32 are added. 12-151-10 AIA 12-51-10 Claim s 1-15 have been canceled. Claims 16-32 are pending in the application, of which claim 23 is withdrawn from consideration. Claim Rejections - 35 USC § 103 07-06 AIA 15-10-15 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. 07-20-aia AIA 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. 07-23-aia AIA 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. 07-20-02-aia AIA This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention. 07-21-aia AIA Claim s 16-22 and 24-32 are rejected under 35 U.S.C. 103 as being unpatentable over Bergmann et al. (WO 2019/086667 A1) . With respect to claims 16 and 18, Bergmann discloses Example 6 (page 59), which is pictured below. PNG media_image1.png 442 502 media_image1.png Greyscale Example 6 is derived from Bergmann Formula I (page 1), which is pictured below. PNG media_image2.png 398 202 media_image2.png Greyscale In Formula I, Example 6 is formed when X is R T , which is pictured below (bottom of page 7 and top of page 3). PNG media_image3.png 198 182 media_image3.png Greyscale In R T of Example 6, both of R N are a C 6 aryl, one of which is substituted with R 6 wherein R 6 is a C 12 heteroaryl (page 7). Bergmann also teaches that R N may have more than one R 6 substituent (page 3), and that examples of R 6 also include a cyano group (page 7). Such a modification produces a compound of instant Formula I when T is a binding site to the second chemical moiety of Formula II, V and W are R I wherein R I is a hydrogen atom, X is R A wherein one of R BN is a cyano group and the other two are hydrogen atoms, and Y is R I and R I is a hydrogen atom, T’, V’, and Y’ are all R II wherein R II is a hydrogen atom, X’ is a cyano group, W’ is a single bond to the second chemical moiety of Formula II, and R 11 through R 15 are hydrogen atoms. In both of Formula II, Z is a direct bond, and all R characters are hydrogen atoms. Bergmann includes each element claimed, with the only difference between the claimed invention and Bergmann being a lack of the aforementioned cyano group being chosen. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible substituents to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a thermally activated delayed fluorescent (TADF) compound which, when used in an organic light-emitting diode (OLED) leads to higher efficiencies and higher stability of the device (page 1, lines 17-20), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E). With respect to claim 17, Bergmann teaches the molecule of claim 16, as discussed above. Examiner would like to note that Bergmann is non-limiting with respect to the bonding position of the R 6 substituents on R N , and also demonstrates a formula wherein W is R A and X’ is CN (see Formula Vb-3 on page 21). Given the general formula and teachings of Bergmann, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of Example 6 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as a TADF compound in the organic layer of the electroluminescent device of Bergmann and possess the properties taught by Bergmann. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP 2144.09 II. Such a positional isomer meets the requirements of the instant claim when T and T’ are each a binding site of the single bond linking the first chemical moiety to the second chemical moieties, and W is R A and X’ is CN. With respect to claims 19 through 21, Bergmann teaches the molecule of claim 16, and the chemical moiety of Formula II is represented by Formula IIa, IIb, and IIc when all R characters are hydrogen atoms, as discussed above. With respect to claim 22, Bergmann teaches the molecule of claim 20, as discussed above. Example 6, pictured and discussed above is derived from Formula III-3 (page 17). In this formula, Bergmann also teaches that any R a - is methyl (page 17, lines 3-4), and the heteroaryl substituent of R 6 may have one or more C 1 alkyl substituents (page 7). Such a modification produces a second chemical moiety of Formula IIb wherein R b is a C 1 alkyl (methyl) group. Bergmann includes each element claimed, with the only difference between the claimed invention and Bergmann being a lack of the aforementioned cyano group being chosen. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible substituents to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a thermally activated delayed fluorescent (TADF) compound which, when used in an organic light-emitting diode (OLED) leads to higher efficiencies and higher stability of the device, commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E). With respect to claim 24, Bergmann teaches the molecule of claim 16, and Bergmann also teaches an optoelectronic device comprising the compound as an emitter or host or electron transport material or a hole injection material or hole blocking material (page 37, lines 4-7). It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound as a material in an optoelectronic device in any of the above roles, as taught by Bergmann. With respect to claim 25, Bergmann teaches the molecule of claim 16, and Bergmann also teaches that the optoelectronic device can be used in any of (page 37): PNG media_image4.png 306 682 media_image4.png Greyscale It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the device in any of the above apparatuses as taught by Bergmann. With respect to claim 26, Bergmann teaches the molecule of claim 16, and Bergmann also teaches a composition (page 38) comprising: PNG media_image5.png 146 706 media_image5.png Greyscale It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the molecule as a material in the claimed composition, as taught by Bergmann. With respect to claim 27, Bergmann teaches the composition of claim 26, and Bergmann also teaches the composition should comprise: PNG media_image6.png 354 712 media_image6.png Greyscale In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). Similarly, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 783, 227 USPQ 773, 779 (Fed. Cir. 1985). See MPEP 2144.05 Obviousness of Similar and Overlapping Ranges, Amounts, and Proportions. In the instant case, the percent composition of each composition component overlaps with the instantly claimed percent compositions. Thus, as the ranges overlap, a prima facie case of obviousness is present. With respect to claim 28, Bergmann teaches the composition of claim 26, and Bergmann also teaches an optoelectronic device comprising a layer formed of the composition (the light emitting layer, page 38) wherein the device is one of (page 37): PNG media_image4.png 306 682 media_image4.png Greyscale It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the composition to form the light emitting layer of an OLED device, as taught by Bergmann. With respect to claim 29, Bergmann teaches the device of claim 24, and the device comprises a substrate, an anode, a cathode, and a light emitting layer between the electrodes (pages 40-41, line 7). It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to form an optoelectronic device using the claimed layer order, as taught by Bergmann With respect to claim 30, Bergmann teaches the molecule of claim 16, and Bergmann also teaches the described optoelectronic devices comprising the compound may be formed using vacuum-deposition (page 55). It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to produce an optoelectronic device using the organic molecule using vacuum-deposition, whereupon, a method for producing the optoelectronic device using vacuum deposition would naturally flow, to arrive at the claimed invention. With respect to claim 31, Bergmann teaches the device of claim 28, and the device comprises a substrate, an anode, a cathode, and a light emitting layer between the electrodes (pages 40-41, line 7). It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to form an optoelectronic device using the claimed layer order, as taught by Bergmann. With respect to claim 32, Bergmann teaches the composition of claim 26, and Bergmann also teaches the described optoelectronic devices comprising the compound may be formed using vacuum-deposition (page 55). It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to produce an optoelectronic device using the composition using vacuum-deposition, whereupon, a method for producing the optoelectronic device using vacuum deposition would naturally flow, to arrive at the claimed invention . Conclusion 07-96 AIA The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Hong et al. (KR 2020/0112730 A) – teaches that when one or more nitrile groups are bonded to the phenyl group bonded to the nitrogen atom of carbazole, the wavelength of the compound shifts to the long wavelength region, increasing the electron acceptor role of the compound, shortening the triplet exciton lifetime, and increasing the rate of RISC (paragraph 0176). Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M.. 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, Jennifer Boyd can be reached at 571-272-7783. 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. /RACHEL SIMBANA/Examiner, Art Unit 1786 Application/Control Number: 18/006,574 Page 2 Art Unit: 1786
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