CTNF 18/153,637 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. KR10-2022-0005424 , filed on 01/13/2022 . Information Disclosure Statement 06-52 AIA The information disclosure statement (IDS) submitted on 04/26/2024 was filed after the mailing date of the instant application on 01/12/2023 . The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner. Claim Objections 07-29-01 AIA Claim s 1 and 4 are objected to because of the following informalities: In claims 1 and 4, one or more CY groups are defined as “phenyl”. In the art of organic chemistry, phenyl denotes monodentate benzene (C 6 H 5 ). In the art of organic electroluminescent molecules, a more appropriate name for a C 6 ring in one of the instant CY group locations is “benzene” . Appropriate correction is required. 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 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2013/0181190 A1) and further in view of Yeager et al. (US 2021/0288269 A1) . With respect to claims 1-5, Ma discloses a heteroleptic iridium complex containing a phenyl pyridine ligand and another ligand containing a dibenzofuran linked to an imidazole or benzimidazole fragment (abstract). Ma gives an example of such a compound in Compound 6-O (page 8 and paragraph 0059 which defines X), which is pictured below. PNG media_image1.png 342 472 media_image1.png Greyscale This compound is derived from Formula I (paragraph 0060) which is pictured below. PNG media_image2.png 368 474 media_image2.png Greyscale Ma also teaches that R 3 can represent disubstitution and adjacent R 3 can be linked (paragraph 0046). However, Ma does not teach nor fairly suggest that two R 3 are joined to form a 5-membered heterocyclic group. In analogous art, Yeager teachers heteroleptic iridium complexes containing benzo-fused ligands (abstract) wherein at least two adjacent substituents on the non-coordinated benzene ring of the dibenzofuran moiety are joined to form a condensed, 5-membered heterocyclic group (paragraph 0013) represented by Formula II, which is pictured below. PNG media_image3.png 240 514 media_image3.png Greyscale In Formula II, Z 1 is selected from the group consisting of O, S, Se, NR, CRR’, and SiRR’ (paragraph 0073), Z 2 is a nitrogen atom, and R B is a phenyl group (see for example the compounds on page 98). Yeager teaches that compounds with these features demonstrate blue-shifted emission and allow for fine tuning of emission color. 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 join two adjacent R 3 in the dibenzofuran moiety of Compound 6-O of Ma to form a condensed, 5-membered ring of Formula II in order to blue-shift the emission color of the organometallic complex as well as allow for fine tuning of emission color, as taught by Yeager. Such a modification produces a compound that meets the requirements of instant Formula 1 when M 1 is iridium, Ln 1 is represented by Formula 1A, Ln 2 is represented by Formula 1B, n1 is 2, and n2 is 1. In Formula 1A, X 1 is a carbon atom and CY 2 is a C 6 carbocyclic (benzene) group, X 2 is a nitrogen atom and CY 1 is a 6-membered heterocyclic (pyridine) group, b10 is 4, b20 is 4, and R 10 and R 20 are both hydrogen atoms. In Formula 1B, X 31 is C(R 31 ), X 32 is C(R 32 ), R 31 and R 32 are joined to form a benzimidazole moiety, a1 is 1 and L 1 is a 1,5-diisopropyl substituted C 6 carbocyclic (phenylene) group, b5 is 1 and R 5 is a C 6 aryl (phenyl) group, Y 1 is an oxygen atom, R 1 and R 2 are hydrogen atoms, CY 41 is a benzene group, CY 42 is one of oxazole (O), thiazole (S), selenazole (Se), pyrrole (CRR’), or azasilole (SiRR’), b40 is 1 and R 40 is a C 6 aryl (phenyl) group. With respect to claim 6, Ma and Yeager teach the compound of claim 1, and the pyridine ring of CY 1 is instant 1-1, as pictured above. With respect to claim 7, Ma and Yeager teach the compound of claim 1, and the benzene group of CY 2 is represented by instant 2-1, as pictured above. With respect to claims 8 and 9, Ma and Yeager teach the compound of claim 1, and R 1 and R 2 are hydrogen atoms, R 3 and R 4 are not present, R 5 is a phenyl group (10-12, claim 9), R 10 and R 20 are hydrogen atoms, R 31 and R 32 are joined to form a benzene ring, and R 40 is a phenyl group (10-12, claim 9), as pictured and discussed above. With respect to claim 10, Ma and Yeager teach the compound of claim 1, as discussed above. Ma also teaches that in Formula I, R 1 which is analogous to instant R 10 can be deuterium (paragraph 0060, line 9). Ma includes each element claimed, with the only difference between the claimed invention and Ma being a lack of the aforementioned deuterium atom being explicitly stated. 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 compound which, when incorporated into OLED devices, can result in devices with improved efficiency and lifetimes (paragraph 0048), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E). With respect to claims 11 through 13, Ma and Yeager teach the compound of claim 1, as discussed above. Applicant will note that Yeager is not limiting with respect to the bonding position of the 5-membered ring on the dibenzoheterole moiety (see for example the formulae on pages 8-10). In this respect, Yeager teaches a compound that can meet the limitations of any of instant Formulae 11-4 through 11-6 (claim 11), instant Formulae 21-7 through 21-12 (claim 12), and instant Formulae 31-7 through 31-12 (claim 13). With respect to claim 14, Ma and Yeager teach the compound of claim 1, and such a compound meets the requirements of at least instant compounds 1, 5, 9, 29, 33, and 37, depending on which 5-membered heterocyclic ring is condensed, and where on the dibenzoheterole the 5-membered ring is condensed.. Please note that these examples are non-limiting and there are additional compounds in the instant claim that may be subject to the same rejection as those explicitly listed. With respect to claims 15-17 and 19, Ma and Yeager teach the compound of claim 1, and Ma also teaches an organic light emitting device comprising an anode, a cathode, and an organic layer between the electrodes comprising the compound of Formula I (paragraph 0060). The organic layer comprises a hole transport region comprising a hole transport layer, an emissive layer, and an electron transporting region comprising an electron transporting layer (paragraph 0037 and Figure 1), and Ma teaches use of the compounds of the invention as a dopant in combination with a host in the emitting layer, and the amount of the dopant is 7, 10, or 13 wt % (Paragraph 0067 and Table 1). 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 of Ma and Yeager as a dopant in the emitting layer of an organic light-emitting device with the claimed device structure, as taught by Ma. With respect to claim 18, Ma and Yeager teach the device of claim 16, as discussed above. Examiner is interpreting the compound of Ma and Yeager to produce a wavelength within the claimed range, which can meet the requirements of the instant claim through its use as a preferred embodiment of the claimed invention, as given through at least any of compounds 1, 5, 9, 29, 33, or 37 which can be found on pages 41-44 of the instant specification. Products of identical chemical composition cannot have mutually exclusive properties, and it has been held that when the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present (See MPEP 2112.01(II)), and the compound of Ma and Yeager reads on the claims. Ma teaches the compounds of the invention demonstrate an emissive wavelength within the claimed range (see Table 2 on page 14) and Yeager teaches that the condensed 5-membered heterocyclic ring results in a blue-shift in emission wavelength. Neither explicitly states what the emission wavelength of such a combination would be. However, this is considered to be a property of the composition. Support for this presumption comes from the use of like materials and like processes when the compound of Ma and Yeager is used as an emissive dopant in the organic layer of an electroluminescent device, which would result in the claimed property described in the instant claims. Therefore, the claims are considered to be obvious over Ma and Yeager, and the burden shifts to applicant to show that there is an unobvious difference between the claimed composition and the composition in the prior art. See MPEP 2112 (V). In addition, the presently claimed properties are considered to be present once the work of Ma and Yeager was first provided. See MPEP 2112.01 (II). With respect to claim 20, Ma and Yeager teach the device of claim 15, and Ma also teaches that optoelectronic devices are suitable for us in apparatuses such as organic phototransistors, organic photovoltaic cells, and organic photodetectors (paragraph 0003). 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 of Ma and Yeager in an apparatus such as an organic phototransistor, as taught by Ma . Conclusion 07-96 AIA The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Xia et al. (US 2011/0057559 A1) – see paragraph [0056] for teaching on a twisted aryl substituent on the (benz)imidazole moiety. Hwang et al. (EP 3792270 A1) – Teaches relevant compounds. Ma et al. (US 2023/0037157 A1) – Teaches imidazole-DBX ligands with condensed rings. 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: 18/153,637 Page 2 Art Unit: 1786
Prosecution Insights