CTNF 18/295,521 CTNF 101399 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 Acknowledgment is made of applicant’s claim for foreign priority based on applications filed in Korea on May 2, 2022. It is noted, however, that the foreign priority date is the effective filing date of the claimed invention if a. The foreign application supports the claimed invention under 112(a), and b. The applicant has perfected the right of priority by providing i. A certified copy of the priority application, and ii. A translation of the priority application (if not in English). In the instant case, the applicant has submitted a certified copy of the priority application, but it is not in English, and the examiner cannot determine if it supports the claimed invention. The effective filing date of the application is considered to be April 4, 2023, which is the actual filing date of instant application 18/295,521. Claim Objections 07-29-01 AIA Claim 14 is objected to because of the following informalities: the Formulae 2-1 contains a Appropriate correction is required. Claim Rejections - 35 USC § 112 07-30-02 AIA The following is a quotation of 35 U.S.C. 112(b): (b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention. The following is a quotation of 35 U.S.C. 112 (pre-AIA), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. 07-34-01 Claim 13 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claim 13 contains a ring labeled as CY25; however, no definition for CY25 has been provided. This renders the claim indefinite because it is unclear what groups may be encompassed by CY25. An interpretation is that CY25 can be selected from any of the cycles defined in claim 1 as being formed from the corresponding R groups. Another interpretation is that CY25 is selected from some smaller subset of those groups. For examination purposes, the claim is interpreted to encompass at least the cycles defined in claim 1. Claim Rejections - 35 USC § 102 07-07-aia AIA 07-07 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 – 07-08-aia AIA (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. 07-12-aia AIA (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. 07-15 AIA Claim s 1-6 and 8-10 are rejected under 35 U.S.C. 102( a)(1) or 35 U.S.C. 102(a)(2 ) as being anticipated by Choi et al. (US20210355148A1, hereinafter "Choi") . In the pertinent art of organic light-emitting devices, Choi discloses an organometallic compound 21 for use in an organic light-emitting device, shown below (¶ [169]). PNG media_image1.png 1318 1931 media_image1.png Greyscale Compound 21 of Choi is also a compound of instant Formula 1 of instant Claim 1 wherein; M1 is a transition metal Ir; L1 is a ligand represented by Formula 1A wherein; X1 is N and X2 is C; R1 is H; R11 is H; b11 is 4; R12 is H (and does not comprise fluorine); b12 is 2; R23 and R24 are bonded together to form a substituted C6 carbocyclic group wherein; R23 is a C4 alkyl group substituted with at least one F; R21 and R22 are H; Formula 1A is a group represented by 3A-1 wherein; CY25 is a benzene group; L2 is a ligand represented by Formula 1B wherein; R31 and R32 is an unsubstituted C6 alkyl group; R31 and R32 is represented by 9-33; R33 is H; n1 is 2 and n2 is 1 wherein; the sum of n1 and n2 is 3; 07-15-02-aia Therefore, the compound 21 of Choi anticipates instant claims 1-6, and 8-10. The applied reference has a common applicant with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2). This rejection under 35 U.S.C. 102(a)(2) might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C. 102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B) if the same invention is not being claimed; or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed in the reference and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement. Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216. Claim Rejections - 35 USC § 103 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. 07-21-aia AIA Claim s 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (US20210355148A1, hereinafter "Choi"), as applied to claim 1-6 and 8-10 as described above . Choi teaches an organometallic compound 21 for use in an organic light-emitting device that reads on instant claims 1-6 and 8-10 as described above. However, Choi does not specifically teach the use of compound 21 in an organic light-emitting device. Choi teaches an organic light-emitting device including a first electrode, a second electrode, and an organic layer located between the electrodes wherein the organic layer includes an emission layer and wherein the organic layer further includes at least one organometallic compound such as the compound 21 as described above (¶ [0180]). Choi teaches the first electrode may be an anode and the second electrode may be a cathode (¶ [0187]). Choi teaches that the organic layer may further include a hole transport region located between the first electrode and the emission layer, and an electron transport region located between the emission layer and the second electrode (¶ [0188]). Choi teaches the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof (¶ [0188]). Choi teaches the organic light-emitting device may be included in an electronic apparatus (¶ [0246]). Choi teaches the claimed invention has a preferred embodiment wherein the emission layer may emit light having a maximum emission wavelength in the range of 600 nm to 650 nm, which substantially overlaps with the claimed range of 590 nm to 650 nm of instant claim 18 (¶ [0183]). Choi teaches the claimed invention above but does not expressly teach the maximum emission wavelength of about 590 nm to 650 nm for an emission layer containing compound 21. It is reasonable to presume that the maximum emission wavelength of about 590 nm to 650 nm is inherent to emission layer containing compound 21. Support for said presumption is found in that an emission layer containing compound 16 of Choi has a substantially similar structure as compound 21 wherein R11 is Me instead of H and the fluorine atom is a position isomer to the adjacent atom. The structural modifications between compounds 16 and 21 have a negligible effect on the maximum emission wavelength of about 590-650 nm, and, therefore, are expected to have the same properties of the claimed invention. Choi teaches an anode, a cathode, and an organic layer and that an organometallic compound is in the organic layer as discussed above. It would have been obvious to use the compound in the organic layer with the device structure of anode, hole transport layer, emission layer containing the Compound 21 of Choi, electron transport layer, and cathode as demonstrated by Choi that this device structure was known prior to the effective filing date of the claimed invention. Therefore, the device of Choi containing compound 21 reads on instant claims 16-20 . 07-21-aia AIA Claim s 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN114075252A, hereinafter "Wang"). Note that a machine-generated translation is provided with this office action . In the pertinent art of organic light-emitting devices, Wang teaches an organometallic complex for use in a light-emitting device with the general Equation 1 wherein the structures LA, LB, and LC are shown below (Description pg 2-4). PNG media_image2.png 1237 2421 media_image2.png Greyscale Wang teaches preferred embodiments of the iridium metal compounds for use in the light-emitting layers of organic electroluminescent devices including compound 1-27, shown below (pg 7, col 3 row 3). PNG media_image3.png 1758 732 media_image3.png Greyscale Compound 1-27 of Wang features an iridium complex with a substituted ligand LA and a substituted ligand LB wherein ring A is a fused tricyclic heterocycle substituted with fluorine. Compound 1-27 features a ligand LB wherein ring B is an unsubstituted naphthalene and ligands LB and LC are the same. Therefore, an organometallic complex where ligand LB and LC are the same wherein (1) ring A features a fused tricyclic nitrogen heterocyclic substituted with fluorene and (2) ring B features a naphthalene is a known and acceptable ligand for the iridium complex of Wang. Compound 1-27 does not contain a C1-C10 alkyl substituted with at least one fluorine for the naphthalene moiety of ring B as required by instant claim 1. Wang teaches that ring B of ligand LB and LC may be substituted with R5 which may be selected from alkyl groups with substitution such as halogen atoms (claim 1, description pg 8). Wang clearly envisioned substituted alkyl groups to include fluorinated groups such as CF3 as evidenced by Compound 1-22 in Wang, shown below (pg 7, col 2, row 2). PNG media_image3.png 1758 732 media_image3.png Greyscale Therefore, CF3 groups are a known and acceptable substituted alkyl group for R5 in ring B of the ligand LB and LC of Wang. Similarly, Ligand LA wherein R1 is CD3, R2 is H, and R3 is CH3 is a known and acceptable ligand for the organometallic complex of Wang. Wang teaches that an organic light-emitting device using the iridium metal complexes within the formula of Wang displays a lower voltage, significantly improved current efficiency, and longer lifespan than existing materials (Table 2). Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the compound 1-27 in the Equation 1 of Wang with (1) a CF3 group in ring B and (2) the ligand LA of compound 1-22 of Wang. The motivation for doing so would have been to create an organic light-emitting device that has an improved voltage, current efficiency, and lifetime as taught by Wang. The Modified Compound of Wang is shown below. PNG media_image4.png 200 400 media_image4.png Greyscale The Modified Compound of Wang is also a compound of instant Formula 1 in instant Claim 1 wherein: M1 is a transition metal Ir; L1 is a ligand represented by Formula 1A wherein; X1 is N and X2 is C; R1 is H; R11 is F; b11 is 1; R12 is H (and does not comprise fluorine); b12 is 2; R21 and R22 are bonded together to form a substituted C6 carbocyclic group; R23 is a C1 alkyl group substituted with at least one fluorine (CF3); R24 is H; Formula 1A is a group represented by 2A-5 wherein; Z4 is F; Formula 1A is a group represented by 3A-3 wherein; CY25 is a C6 carbocyclic group (benzene); R25 is H and b25 is 4; Formula 1A is a group represented by 3A-13 R23 is CF3; R24 is H; R25 is H and b25 is 4; Formula 1A is a group represented by 3A-27 wherein; Z23 is CF3; Z25 is H and b25 is 4; Formula 1A is a group represented by 1A-3 wherein; R13-R15 is H; R16 is F; R23 is CF3; R24 is H; R25 is H and b25 is 4; L2 is a ligand represented by Formula 1B wherein; R31 is CD3; R32 is CH3; R33 is H; n1 is 2 and n2 is 1 wherein; the sum of n1 and n2 is 3; the organometallic compound is represented by Formulae 2-3 wherein; R23 is CF3 as defined for R11 in claim 1. Therefore, the Modified Compound of Wang reads on instant claims 1-14. Regarding instant claims 16-20, Wang teaches that an organometallic compound of Equation 1 may be used in an organic light-emitting device having a structure of the following layers stacked on top of another: ITO, CuPc, NPB, CBP and an organometallic compound of Equation 1, Alq3, LiF, and Al (Table 2, Application example 1). Therefore, the layer containing ITO reads on the first electrode as an anode, and the layer containing Al reads on the second electrode as a cathode. The layers containing CuPc, NPB, CBP and an organometallic compound of Equation 1, Alq3, and LiF read on the organic layer arranged between the first and second electrode wherein the layer containing CBP and the organometallic compound reads on the emission layer. The layer containing CuPc reads on the hole injection layer; the layer containing NPB reads on the hole transport layer; and, together, the two layers read on the hole transport region. The layer containing Alq3 reads on the electron transport layer; the layer containing NPB reads on the electron injection layer; and, together, the two layers read on the electron transport region. Wang teaches the claimed invention above but does not expressly teach the maximum emission wavelength of the Modified Compound of Wang is between 590 nm to 650 nm. It is reasonable to presume that the maximum emission wavelength is between 590 nm to 650 nm is inherent to the Modified Compound of Wang. Support for said presumption is found in that of the Modified Compound of Wang has a substantially similar structure to instant compound 3 which has an emission of 618 nm (instant Specification Table 2). Instant compound 3 is the same as the Modified Compound of Wang except ring B is a different positional isomer, and ligand LA wherein R31 is CH3 instead of CD3. Therefore, the Modified Compound of Wang and instant compound 3 are expected to have the same properties of the maximum emission wavelength being between 590 nm to 650 nm. Wang teaches an anode, a cathode, and an organic layer and the organometallic compound is in the organic layer as discussed above. It would have been obvious to use the Modified Compound of Wang in the organic layer with the device structure of anode, hole transport layer, emission layer including the Modified Compound of Wang, electron transport layer, and cathode as Wang demonstrates this device structure was known prior to the effective filing date of the claimed invention. The resulting Modified Device of Wang would contain the same structure as the Application example 1, described above, except the light-emitting layer contains the Modified Compound of Wang. Therefore, the Modified Device of Wang reads on instant claims 16-20. Regarding instant claim 15, Wang teaches the Modified Compound of Wang as described above; however, the Modified Compound of Wang differs from claimed compound 3 in that (1) Formula 1A is represented as 3A-3 instead of 3A-1 and (2) Formula 1B has R31 as CD3 instead of CH3. PNG media_image5.png 794 1775 media_image5.png Greyscale Wang teaches that a C-D bond is comparable, within an order of magnitude, to a C-H bond when it comes to stability (Description pg 2). Therefore, a CH3 group is a known and acceptable alternative to a CD3 group for the LA ligand of the organometallic complex of Wang. Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the LA and LB ligand in the Modified Complex of Wang with (1) an LA ligand where R1 is CH3 and (2) an LB ligand where ring B is the naphthalene position isomer of Wang. The motivation for doing so would have been to create an organic light-emitting device that an improved voltage, current efficiency, and lifetime as taught by Wang. Given the general formula and teachings of Wang, 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 the Modified Compound of Wang wherein the naphthalene, of ring B ligand LB, is moved. Wang teaches naphthyl groups as suitable groups for ring B in the ligands LB or LC, and Wang does not restrict or limit the particular bonding pattern of the naphthyl group either to ring A or to the metal center. One of ordinary skill in the pertinent art would have been motivated to produce additional positional isomers of the compound represented by the naphthalene of ring B ligand LB in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as organometallic complex in the light-emitting layer of the organic light-emitting device of Wang and possess the properties of an improved voltage, current efficiency, and lifetime as taught by Wang. 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. The resulting Modified Compound 2 of Wang is shown below. PNG media_image6.png 200 400 media_image6.png Greyscale Modified Compound 2 of Wang Therefore, the Modified Compound 2 of Wang reads on instant claim 15 because it is the same as instant compound 3 . Double Patenting 08-33 AIA 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. 08-34 AIA Claim s 1-6 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of U.S. Patent No. 12152042B2 (hereinafter '042) . Although the claims at issue are not identical, they are not patentably distinct from each other because ligands of Formula 1A in instant claim 1 overlap in scope with compounds of Formula 1 in claim 1 of '042. The overlap in scope is evidenced by compound 21 in claim 14 of ‘042, shown below (claim 14) . PNG media_image7.png 1175 1626 media_image7.png Greyscale Compound 21 of ‘042 is a compound of instant Claim 1 wherein: M1 is a transition metal Ir; L1 is a ligand represented by Formula 1A wherein; X1 is N and X2 is C; R1 is H; R11 is H; b11 is 4; R12 is H (and does not comprise fluorine); b12 is 2; R23 and R24 are bonded together to form a substituted C6 carbocyclic group wherein; R23 is a C4 alkyl group substituted with at least one F; R21 and R22 are H; Formula 1A is a group represented by 3A-1 wherein; CY25 is a benzene group; L2 is a ligand represented by Formula 1B wherein; R31 and R32 is an unsubstituted C6 alkyl group; R31 and R32 is represented by 9-33; R33 is H; n1 is 2 and n2 is 1 wherein; the sum of n1 and n2 is 3; Therefore, instant claims 1-6 claims the same invention as that of claim 1 of prior U.S. Patent No. 12152042B2. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to LUCAS Q NGUYEN whose telephone number is (571)272-1199. The examiner can normally be reached Monday - Thursday 7:30 am - 5:00 pm Fridays 7:45 am to 12:00 pm. 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. /L.Q.N./Examiner, Art Unit 1786 /MARLA D MCCONNELL/Supervisory Patent Examiner, Art Unit 1789 Application/Control Number: 18/295,521 Page 2 Art Unit: 1786 Application/Control Number: 18/295,521 Page 3 Art Unit: 1786 Application/Control Number: 18/295,521 Page 4 Art Unit: 1786 Application/Control Number: 18/295,521 Page 5 Art Unit: 1786 Application/Control Number: 18/295,521 Page 6 Art Unit: 1786 Application/Control Number: 18/295,521 Page 7 Art Unit: 1786 Application/Control Number: 18/295,521 Page 8 Art Unit: 1786 Application/Control Number: 18/295,521 Page 9 Art Unit: 1786 Application/Control Number: 18/295,521 Page 10 Art Unit: 1786 Application/Control Number: 18/295,521 Page 11 Art Unit: 1786 Application/Control Number: 18/295,521 Page 12 Art Unit: 1786 Application/Control Number: 18/295,521 Page 13 Art Unit: 1786 Application/Control Number: 18/295,521 Page 14 Art Unit: 1786 Application/Control Number: 18/295,521 Page 15 Art Unit: 1786 Application/Control Number: 18/295,521 Page 16 Art Unit: 1786 Application/Control Number: 18/295,521 Page 17 Art Unit: 1786 Application/Control Number: 18/295,521 Page 18 Art Unit: 1786 Application/Control Number: 18/295,521 Page 19 Art Unit: 1786 Application/Control Number: 18/295,521 Page 20 Art Unit: 1786
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