CTNF 18/195,730 CTNF 95671 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. Specification 07-29 AIA The disclosure is objected to because of the following informalities: the specification contains blurry structures . Appropriate correction is required. Claim Objections 07-29-01 AIA Claim s 10-12 are objected to because of the following informalities: Claims 10-11 contain blurry structures. For consistency and ease of reading, it is recommended in claim 12 to replace “the at least emitting material layer” in line 6 with “the at least one emitting material layer”. For ease of reading, it is recommended in line 5 of claim 22 to replace “including second emitting material layer” with “including a second emitting material layer” . 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 1-7, 12-18, 21, and 25 are rejected under 35 U.S.C. 103 as being unpatentable over Dyatkin (US 2020/0361974 A1) in view of Shih (US 2022/0298190 A1) . Regarding claims 1-2, 4-7, 12-13, 15-18, 21, and 25 , Dyatkin teaches an organic light emitting device having improved stability by comprising a phosphorescent emitter having a metal M and a first ligand L A having the structure of Formula I, which may be further represented by Formula IX (abstract; ¶ [0006]-[0007] and [0055]). In particular, the organic light emitting device includes a substrate, an anode, a cathode, and an emissive layer therebetween, wherein the emissive layer contains a host and the phosphorescent emitter as a dopant (¶ [0074], [0083], [0089], [0104], [0118]). Dyatkin teaches examples of compounds having a first ligand L A having the structure of Formula I including the compound below on pg. 69. Formula IX: PNG media_image1.png 171 171 media_image1.png Greyscale Dyatkin’s compound: PNG media_image2.png 176 177 media_image2.png Greyscale Dyatkin’s compound fails to read on the claimed formula as it contains phenyl rather than naphthyl in the location of ring C. However, Dyatkin does teach R C may be substituents which join or fuse to form a ring (¶ [0055]). Additionally, Dyatkin teaches examples of compounds having a first ligand L A having the structure of Formula I wherein the ring C moiety is a naphthyl group, as shown by the compound below on pg. 69. Dyatkin’s compound on pg. 69: PNG media_image3.png 100 84 media_image3.png Greyscale Shih teaches a compound of Formula Ir(L A )(L B )(L C ) for use in OLEDs, wherein examples thereof include the inventive example on pg. 175 (abstract). In a comparison with the comparative example, the compound of Formula Ir(L A )(L B )(L C ) provides a more saturated color with narrower line shape due to the naphthalene as the bottom ring in the ligand structure (¶ [0211]). Inventive example: PNG media_image4.png 213 360 media_image4.png Greyscale Comparative example: PNG media_image5.png 213 359 media_image5.png Greyscale Therefore, in Dyatkin’s compound, 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 phenyl with naphthalene PNG media_image3.png 100 84 media_image3.png Greyscale , as shown in Dyatkin’s compound on pg. 69, based on the teaching of Shih. The motivation for doing so would have been to provide a compound with a more saturated color with narrower line shape, as taught by Shih. The modified compound of Dyatkin in view of Shih is reproduced below in comparison to the claimed Chemical Formula 2. modified compound: PNG media_image6.png 359 322 media_image6.png Greyscale Formula 2: PNG media_image7.png 94 235 media_image7.png Greyscale The modified compound reads on the claimed Chemical Formula 1 of Ir(L A ) 3 and reads on the claimed Chemical Formulas 2, 3, and 5 ( claims 1-2, 4, 13, 15 ) wherein: X 1 to X 4 is CR 1 ; X 5 is CR 2 ; Y 1 and Y 2 are each CR 5 R 6 ; Each R 1 is hydrogen, one R 5 and one R 6 are each halogen, and one R 5 and one R 6 are each an unsubstituted C 1 alkyl group; and a1 and a4 are each 4, and a2 and a3 are each 2. Per claims 5 and 16 , as n is 0, L B is not required to be present. Per claims 6-7 and 17-18 , as discussed above, each of X 1 to X 4 is CR 1 wherein each R 1 is hydrogen (protium); X 5 is CR 2 wherein R 2 is hydrogen (protium). Regarding claims 3 and 14 , Dyatkin in view of Shih teach the device comprising the modified compound, as described above with respect to claims 1 and 12. Formula I: PNG media_image8.png 69 159 media_image8.png Greyscale modified compound: PNG media_image6.png 359 322 media_image6.png Greyscale The modified compound fails to read on the claimed Chemical Formula 4. However, the modified compound contains a first ligand L A having the structure of Formula I, wherein Z 1 and Z 2 are each independently selected from the group consisting of a direct bond, CR 1 CR 2 , and CR 1 R 2 CR 3 R 4 , and no more than one of Z 1 and Z 2 is a direct bond (abstract; ¶ [0007]). Therefore, given the general formula and teachings of Dyatkin, 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 direct bond of Z 1 with CR 1 R 2 CR 3 R 4 wherein R 1 and R 2 are each F and R 3 and R 4 are each methyl (as shown in the compound on pg. 69) and to substitute CR 1 R 2 CR 3 R 4 of Z 2 with a direct bond (as shown in the compound on pg. 69) , because Dyatkin teaches Z 1 and Z 2 may suitably be selected as a direct bond and CR 1 R 2 CR 3 R 4 . The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as a phosphorescent emitter in the device of Dyatkin in view of Shih and possess the benefits taught by Dyatkin and Shih. See MPEP 2143.I.(B). The modified compound reads on the claimed Chemical Formula 4 . 07-22-aia AIA Claim s 22-24 are rejected under 35 U.S.C. 103 as being unpatentable over Dyatkin (US 2020/0361974 A1) in view of Shih (US 2022/0298190 A1) as applied to claim 12 above, and further in view of Yamamoto (US 2022/0020945 A1) . Regarding claims 22-24 , Dyatkin in view of Shih teach the organic light emitting device comprising an emissive layer containing the modified compound, as described above with respect to claim 12. Dyatkin in view of Shih fail to teach the emissive layer includes multiple emitting parts and charge generating layers. However, as discussed above, the modified compound is a phosphorescent emitter. Yamamoto teaches OLED devices including a symmetric emissive-layer architecture, which improves the color stability of the device (abstract). In particular, the device includes the structure of: first emissive layer comprising a first fluorescent emissive material/first charge generation layer/second emissive layer comprising an emissive material/third emissive layer comprising an emissive material/fourth emissive layer comprising an emissive material/second charge generation layer/fifth emissive layer comprising a second fluorescent emissive material (claim 1; ¶ [0057]). 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 include additional layers in the emissive layer of the device of Dyatkin in view of Shih such that it contains the following layers: a first emissive layer comprising a first fluorescent emissive material /a first charge generation layer/a second emissive layer comprising an emissive material/a third emissive layer comprising an emissive material/a fourth emissive layer comprising an emissive material/a second charge generation layer/ fifth emissive layer comprising a second fluorescent emissive material , wherein the modified compound is provided in one of the emissive layers, based on the teaching of Yamamoto. The motivation for doing so would have been to improve the color stability of the device, as taught by Yamamoto. In particular, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to provide the modified compound in one of the second emissive layer, the third emissive layer, or the fourth emissive layer, because it would have been choosing from one of five emissive layers in which to place the modified compound, which would have been a choice from a finite number of identified, predictable solutions of the device of Dyatkin in view of Shih and Yamamoto and possessing the benefits taught by Dyatkin, Shih, and Yamamoto. One of ordinary skill in the art would have been motivated to produce additional devices having the benefits taught by Dyatkin, Shih, and Yamamoto in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E). The resulting device comprises the following structure: first emissive layer ( first emitting material layer )/first charge generation layer/second emissive layer comprising an emissive material ( first layer )/a third emissive layer comprising an emissive material ( first layer )/a fourth emissive layer ( second layer )/second charge generation layer/second emitting layer ( third emitting material layer ), wherein one of the second, third, or fourth emissive layer comprises the modified compound . Allowable Subject Matter 12-151-08 AIA 07-43 12-51-08 Claim s 8-11 and 19-20 are 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. 13-03-01 AIA The following is a statement of reasons for the indication of allowable subject matter: With respect to claims 8-9 and 19-20 , the prior art does not teach or suggest an organometallic compound represented by a structure of Chemical Formula 1 wherein L A has a structure of Chemical Formula 2 wherein each of X 1 -X 4 is CR 1 and each of Y 1 and Y 2 are CR 5 R 6 , wherein R 1 is independently protium, deuterium, a C 1 -C 10 alkyl group, or a C 6 -C 30 aryl group, and R 2 to R 6 is independently protium, deuterium, or a C 1 -C 10 alkyl group, in combination with the remainder of claims 8-9 and 19-20. Chemical Formula 2: PNG media_image7.png 94 235 media_image7.png Greyscale With respect to claims 10-11 , the prior art does not teach or suggest an organometallic compound having the structure of the claimed compounds 1-240, wherein each of the claimed compounds comprise a substituted or unsubstituted moiety PNG media_image7.png 94 235 media_image7.png Greyscale selected from the following groups: 5,6-dihydrobenz[ f ]isoquinoline, 5,6-dihydrobenzo[ h ]quinazoline, 2,10-dihydrophenanthroline, 2,9-dihydrophenanthroline, 2,8-dihydrophenanthroline, and 2,7-dihydrophenanthroline, and wherein the substituents are selected from a C 1 -C 4 alkyl group or a phenyl group, in combination with the remainder of claims 10-11. Dyatkin (US 2020/0361974 A1), cited in the rejection above, is considered the closest prior art of record. Dyatkin teaches an organic light emitting device having improved stability by comprising a phosphorescent emitter having a metal M and a first ligand L A having the structure of Formula I (abstract; ¶ [0006]-[0007] and [0055]). Dyatkin teaches examples of compounds having a first ligand L A having the structure of Formula I including the compound below on pg. 69. Formula I: PNG media_image8.png 69 159 media_image8.png Greyscale Dyatkin’s compound: PNG media_image2.png 176 177 media_image2.png Greyscale In Formula I, Z 1 and Z 2 are each independently selected from the group consisting of a direct bond, CR 1 R 2 , and , CR 1 R 2 R 3 R 4 (¶ [0007]). Dyatkin teaches in Formula I at least one of R 1 to R 4 is a fluorine atom (¶ [0007]). Accordingly, the claimed Chemical Formula 2 wherein each of X 1 -X 4 is CR 1 , X 5 is CR 2 , and each of Y 1 and Y 2 are CR 5 R 6 wherein R 1 is protium, deuterium, a C 1 -C 10 alkyl group, or a C 6 -C 30 aryl group, and R 2 to R 6 is protium, deuterium, or a C 1 -C 10 alkyl group is not within the scope of Dyatkin’s Formula I. Additionally, an organometallic compound comprising an unsubstituted or substituted moiety selected from the following groups: 5,6-dihydrobenz[ f ]isoquinoline, 5,6-dihydrobenzo[ h ]quinazoline, 2,10-dihydrophenanthroline, 2,9-dihydrophenanthroline, 2,8-dihydrophenanthroline, and 2,7-dihydrophenanthroline, wherein the substituents are selected from a C 1 -C 4 alkyl group or a phenyl group is not within the scope of Dyatkin’s Formula I. Wang (English translation of WO 115197273 A obtained from Global Dossier) is considered relevant to the claimed invention. Wang teaches a compound represented by formula (I) wherein examples thereof include the compound below on pg. 4 (beginning of pg. 2). formula (I): PNG media_image9.png 337 343 media_image9.png Greyscale Wang’s compound: PNG media_image10.png 103 121 media_image10.png Greyscale The compounds represented by Wang’s formula (I) fail to read on the claimed Chemical Formula 2 as the instant claims do not explicitly recite R 1 and R 2 may be further linked together to form an aromatic ring. Accordingly, Wang fails to remedy the deficiencies of Dyatkin. Cao (US 2020/0381633 A1) is considered relevant to the claimed invention. Cao teaches a compound represented by the formula M(LA) x (LB) y (LC) z wherein examples thereof include P141 (abstract; pg. 62). P141: PNG media_image11.png 165 198 media_image11.png Greyscale P141 fails to read on the claimed Chemical Formula 2 as the instant claimed X 1 -X 2 -X 3 -X 4 containing ring cannot fuse with the N-X 5 containing ring. Accordingly, Cao fails to remedy the deficiencies of Dyatkin. Thus there is no prior art, either alone or in combination, which teaches or renders obvious an organometallic compound represented by a structure of Chemical Formula 1 wherein L A has a structure of Chemical Formula 2 wherein each of X 1 -X 4 is CR 1 and each of Y 1 and Y 2 are CR 5 R 6 , wherein R 1 is independently protium, deuterium, a C 1 -C 10 alkyl group, or a C 6 -C 30 aryl group, and R 2 to R 6 is independently protium, deuterium, or a C 1 -C 10 alkyl group, in combination with the remainder of claims 8-9 and 19-20. Likewise, there is no prior art, either alone or in combination, which teaches or renders obvious an organometallic compound having the structure of the claimed compounds 1-240, wherein each of the claimed compounds comprise a substituted or unsubstituted moiety PNG media_image7.png 94 235 media_image7.png Greyscale selected from the following groups: 5,6-dihydrobenz[ f ]isoquinoline, 5,6-dihydrobenzo[ h ]quinazoline, 2,10-dihydrophenanthroline, 2,9-dihydrophenanthroline, 2,8-dihydrophenanthroline, and 2,7-dihydrophenanthroline, and wherein the substituents are selected from a C 1 -C 4 alkyl group or a phenyl group, in combination with the remainder of claims 10-11. Contact Information Any inquiry concerning this communication or earlier communications from the examiner should be directed to BRAELYN R WATSON whose telephone number is (571)272-1822. The examiner can normally be reached M-F 7:30am-5pm. 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. /BRAELYN R WATSON/Examiner, Art Unit 1786 Application/Control Number: 18/195,730 Page 2 Art Unit: 1786 Application/Control Number: 18/195,730 Page 3 Art Unit: 1786 Application/Control Number: 18/195,730 Page 4 Art Unit: 1786 Application/Control Number: 18/195,730 Page 5 Art Unit: 1786 Application/Control Number: 18/195,730 Page 6 Art Unit: 1786 Application/Control Number: 18/195,730 Page 7 Art Unit: 1786 Application/Control Number: 18/195,730 Page 9 Art Unit: 1786 Application/Control Number: 18/195,730 Page 10 Art Unit: 1786 Application/Control Number: 18/195,730 Page 11 Art Unit: 1786 Application/Control Number: 18/195,730 Page 12 Art Unit: 1786 Application/Control Number: 18/195,730 Page 13 Art Unit: 1786 Application/Control Number: 18/195,730 Page 14 Art Unit: 1786
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