CTFR 17/516,647 CTFR 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. 12-151 AIA 26-51 12-51 Status of Claims Claims 1, 4, 9, 14, and 21 are amended, claims 28-33 are new, and claims 22-27 are cancelled due to Applicant's amendment dated 03/11/202. Claims 1-2, 4, 8-9, 11-14, 16-18, 20-21, and 28-33 are pending. Response to Amendment The rejections of claims 22-27 as set forth in the previous Office Action are moot because claims 22-27 are cancelled due to the Applicant's amendment dated 03/11/2026. The objection to claims 1 and 21 as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 03/11/2026. The rejection of claims 1-2, 4, 8-9, 12-14, 16-18, and 20-21 under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA), first paragraph, as failing to comply with the written description requirement as set forth in paragraphs 22-23 of the previous Office Action is overcome due to the Applicant's amendment dated 03/11/2026. The rejection is withdrawn . The rejection of claims 1-2, 4, 8-9, 12-14, 16-18, and 20-21 under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA), first paragraph, as failing to comply with the written description requirement as set forth in paragraph 24 of the previous Office Action is not overcome due to the Applicant's amendment dated 03/11/2026. The rejection is herein revised to reflect the amended claim language. The rejection of claim 9 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 as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 03/11/2026. The rejection is withdrawn . The rejection of claims 1-2, 4, 8-9, 11-14, 17-18, and 20-21 under 35 U.S.C. 103 as being unpatentable over Adamovich (US 2019/0280213 A1) in view of Tomohiri (English translation of JP 2006120905 A obtained from Espacenet) is overcome due to the Applicant's amendment dated 03/11/2026. The rejection is withdrawn . The rejection of claims 1-2, 8-9, 11-14, 17-18, and 20-21 under 35 U.S.C. 103 as being unpatentable over Boudreault ‘818 (US 2019/0248818 A1) in view of Tomohiri is overcome due to the Applicant's amendment dated 03/11/2026. The rejection is withdrawn . The rejection of claims 1-2, 4, 8-9, 11, 13, 16-18, and 20 under 35 U.S.C. 103 as being unpatentable over Itoh (US 2007/0103060 A1) in view of Boudreault (US 2015/0236276 A1) and Lamansky (Lamansky, Sergey, et al. “Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes.” Journal of the American Chemical Society 123.18(2001):4304-4312) is overcome due to the Applicant's amendment dated 03/11/2026. The rejection is withdrawn . Response to Arguments Applicant’s arguments on pages 64-72 of the reply dated 07/09/2025 with respect to the rejection of claims 1-2, 4, 8-9, 11-14, 16-18, 20-21 as set forth in the previous Office Action have been fully considered but they are not persuasive . Applicant's argument –On pages 67-68, Applicant points to paragraphs [0056], [0064], and [0065] of the specification for support of the amended proviso (v). Examiner's response –While paragraphs [0056], [0064], and [0065] provide support for most of the proviso (v), they do not provide sufficient support for the full scope of wherein two R C are joined or fused to form a ring system fused to ring C, wherein the ring system comprises at least two rings and comprises a 6-membered ring fused to ring C. That is, in proviso (v), X 3 and X 4 may be C or N . However, instant paragraph [0056] recites X 3 and X 4 are C , and two R C are joined to form a ring system fused with ring C, and in some embodiments, the ring system comprises at least two rings fused to ring C, wherein at least one of the at least two rings fused to ring C is a 6-membered ring. The embodiments shown in paragraphs [0064] and [0065] show further support for wherein X 3 and X 4 are C and two R C are joined to form a ring system fused with ring C, and in some embodiments, the ring system comprises at least two rings fused to ring C, wherein at least one of the at least two rings fused to ring C is a 6-membered ring. As proviso (v) allows for X 3 and X 4 to be C or N , the rejection under 35 U.S.C. 112(a) has not been overcome. Applicant's argument –On pages 68-72, Applicant argues that the prior art fails to read on the claims as amended which require one of provisos (i) to (v) to be satisfied. Examiner's response –For the reasons discussed in the new grounds of rejection below, the newly cited references met the claims as amended. Claim Objections 07-29-01 AIA Claim s 21, 28, 30, and 33 are objected to because of the following informalities: It appears the periods of claims 21 and 30 are deleted. As claim 28 is a newly added claim, claim 28 is objection to for being indicated as “(Currently Amended)” rather than “(New)”. Claim 33 recites “RB” rather than “R B ” as it is previously referred to in claim 1 . Appropriate correction is required. Claim Rejections - 35 USC § 112 07-30-01 AIA The following is a quotation of the first paragraph of 35 U.S.C. 112(a): (a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention. The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112: The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention. 07-31-01 Claims 1-2, 4, 8-9, 11-14, 16-18, 20-21, and 28-33 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention. Claims 1 and 4, recite the limitation wherein two R C are joined or fused to form a polycyclic ring system fused to ring C, wherein the ring system comprises at least two rings and comprises a 6-membered ring fused to ring C. The instant specification recites any two adjacent R C may be joined or fused to form a ring (instant ¶ [0050]). The instant specification further recites the ligand L A may be selected from the structures L Ai-1-X to L Ai-108-X wherein LAi-21-X to L Ai-32-X and L Ai-57-X to L Ai-88-X are examples of ligands wherein two are joined or fused to form a polycyclic ring system comprising a 6-membered ring fused to ring C (instant ¶ [0065] and pgs. 11-12). The instant specification recites in some embodiments, X 3 and X 4 are C, and two R C are joined to form a ring system fused with ring C, and in some embodiments, the ring system comprises at least two rings fused to ring C, wherein at least one of the at least two rings fused to ring C is a 6-membered ring (instant ¶ [0056]). Accordingly, while there is support in the instant specification for: 1) wherein any two adjacent R C are joined or fused to form a ring, 2) wherein the ligand L A is selected from the structures L Ai-1-X to L Ai-108-X , and 3) X 3 and X 4 are C , and two R C are joined to form a ring system fused with ring C, and in some embodiments, the ring system comprises at least two rings fused to ring C, wherein at least one of the at least two rings fused to ring C is a 6-membered ring, there is not sufficient support for the full scope of wherein two R C are joined or fused to form a ring system fused to ring C, wherein the ring system comprises at least two rings and comprises a 6-membered ring fused to ring C. For this reason, claims 1 and 4 are considered to have new matter. Claims 1 and 30 recite the newly amended proviso (ii) that requires at least one R B comprises alkyl or cycloalkyl comprising at least 3 carbon atoms. The instant specification recites R B is a substituent selected from the group consisting of the general substituents, wherein the general substituents are selected from groups consisting of deuterium, halogen, alkyl, etc. (¶ [0039] and [0050]). Additionally, the instant specification recites the ligand L A may be selected from the group consisting of L Ai-m-X wherein G (corresponding to the claimed ring B) may be selected from the structures of G 1 to G 52 (¶ [0065]). G 1 to G 52 provide support for R B being alkyl groups of isopropyl and t-butyl (see structures on instant pg. 41). Thus, while there is support for wherein R B is an alkyl or is specifically selected from isopropyl and t-butyl, there is not sufficient support for the full scope of R B comprising an alkyl or cycloalkyl comprising at least 3 carbon atoms. For this reason, claims 1 and 30 are considered to have new matter Claims 2, 4, 8-9, 11-14, 16-18, 20-21, and 28-33 are rejected for being dependent upon claim 1. Claim Rejections - 35 USC § 103 07-103 AIA The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action. 07-21-aia AIA Claim s 1-2, 8-9, 11-13, 17-18, 20, and 30-31 are rejected under 35 U.S.C. 103 as being unpatentable over Choi (US 2019/0326527 A1) in view of Yang (Yang, B. N., and D. M. Shin. "The Synthesis and Properties of Solution Processable a Red Phosphorescent Iridium (III) Complex with Alkyl Group." Journal of Nanoscience and Nanotechnology 16.3 (2016): 2696-2700.) Regarding claims 1-2, 8-9, 11-13, 17-18, 20, and 30-31 , Choi teaches an organic light-emitting device having improved luminescent efficiency by including an organometallic compound represented by Formula 1, wherein L 1 is represented by Formula 2 (abstract; ¶ [0010] and [0143]-[0144]). Examples of such devices include the device of Example 1, which includes an anode, an emission layer comprising a host of CBP and a dopant of Compound 1, and a cathode (¶ [0279]-[0282]; Table 4 on pg. 71; compound structure on pg. 70) 2: PNG media_image1.png 164 232 media_image1.png Greyscale 1: PNG media_image2.png 138 335 media_image2.png Greyscale Compound 1 fails to read on the claimed Formula I as it does not include a 5-membered ring in the location of CY 21 . However, Choi does teach CY 21 may be a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group wherein examples thereof include thiophene (¶ [0018] and [0055]). Yang teaches (TMP-HT) 2 Ir(acac), which is an iridium-based organometallic complex for use in an organic light-emitting diode (abstract; Figure 1 on pg. 2697). The (TMP-HT) 2 Ir(acac) comprises an alkyl-substituted thiophene group, wherein the thiophene group increases electron density and the alkyl group has hydrophobic property (abstract). Electron density helps with intramolecular charge transfer, and hydrophobic property is beneficial for solution processes (abstract; second paragraph of Introduction on pg. 2696). (TMP-HT) 2 Ir(acac): PNG media_image3.png 149 86 media_image3.png Greyscale 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 substituted phenyl group in the location of CY 21 in Compound 1 with a hexyl-substituted thiophene group as shown in (TMP-HT) 2 Ir(acac), as taught by Yang. The motivation for doing so would have been to provide a complex with increased electron density and hydrophobic property, as taught by Yang. The modified Compound 1 is reproduced below in comparison to the claimed Formula I. modified 1: PNG media_image4.png 368 452 media_image4.png Greyscale Formula I: PNG media_image5.png 173 144 media_image5.png Greyscale The modified Compound 1 reads on the claimed Formula I and II ( claims 1 and 8 ) wherein: X 1 to X 8 is C; Y 1’ is O and Y 2’ is S; R A is hydrogen, R B is alkyl, R C is a combination of aryl and alkyl ( claim 2 ); and M is Ir. The modified Compound 1 satisfies the provisos (ii) and (iii) wherein at least one R B comprises alkyl comprising at least 3 carbon atoms, and no two R C are joined to form a ring and at least one R C comprises aryl ( claims 30-31 ). Additionally, the modified Compound 1 meets the limitations of: PNG media_image6.png 170 143 media_image6.png Greyscale ( claim 9 ); M(L A ) 2 (L B ) 1 ( claims 11-12 ); PNG media_image7.png 116 127 media_image7.png Greyscale wherein R a1 and R c1 are each alkyl groups and R b1 is hydrogen ( claim 13 ). Per claim 18 , the host of CBP comprises a carbazole chemical moiety (see structure on pg. 71 of Choi). Per claim 20 , an organic light-emitting device may be considered a consumer product . 07-21-aia AIA Claim s 1-2, 8-9, 11-14, 17-18, 20-21, 29, 31, and 33 are rejected under 35 U.S.C. 103 as being unpatentable over Choi (US 2019/0326527 A1) in view of Cho (Cho, Woosum, et al. "Highly efficient, conventional and flexible deep-red phosphorescent OLEDs using ambipolar thiophene/selenophene-phenylquinoline ligand-based Ir (III) complexes." Dyes and Pigments 136 (2017): 390-397.) Regarding claims 1-2, 8-9, 11-14, 17-18, 20-21, 29, 31, and 33 , Choi teaches an organic light-emitting device having improved luminescent efficiency by including an organometallic compound represented by Formula 1, wherein L 1 is represented by Formula 2 (abstract; ¶ [0010] and [0143]-[0144]). Examples of such devices include the device of Example 1, which includes an anode, an emission layer comprising a host of CBP and a dopant of Compound 1, and a cathode (¶ [0279]-[0282]; Table 4 on pg. 71; compound structure on pg. 70) 2: PNG media_image1.png 164 232 media_image1.png Greyscale 1: PNG media_image2.png 138 335 media_image2.png Greyscale Compound 1 fails to read on the claimed Formula I as it does not include a 5-membered ring in the location of CY 21 . However, Choi does teach CY 21 may be a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group (¶ [0018] and [0055]). Additionally, Choi teaches the organometallic compound represented by Formula 1 may emit red light (¶ [0139]). Cho teaches phosphorescent OLEDs comprising iridium-based complexes including (Se-PQ) 3 Ir (abstract; Scheme 1 on pg. 391). (Se-PQ) 3 Ir contains selenophene which provides the compound with a saturated deep-red emission (Conclusion on pg. 396; second paragraph of Result and discussion on pg. 383-394). (Se-PQ) 3 Ir: PNG media_image8.png 190 169 media_image8.png Greyscale 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 substituted phenyl group in the location of CY 21 in Compound 1 with a selenophene group as shown in (Se-PQ) 3 Ir, as taught by Cho. The motivation for doing so would have been to provide a compound with a saturated deep-red emission, as taught by Cho. The modified Compound 1 is reproduced below in comparison to the claimed Formula I. modified 1: PNG media_image9.png 235 446 media_image9.png Greyscale Formula I: PNG media_image5.png 173 144 media_image5.png Greyscale The modified Compound 1 reads on the claimed Formula I and II ( claims 1 and 8 ) wherein: X 1 to X 8 is C; Y 1’ is O and Y 2’ is Se; R A and R B are each hydrogen, R C is a combination of aryl and alkyl ( claim 2 ); and M is Ir. The modified Compound 1 satisfies the provisos (i) and (iii) wherein Y 2’ is Se, and no two R C are joined to form a ring and at least one R C comprises aryl ( claims 29 and 31 ). Additionally, the modified Compound 1 meets the limitations of: PNG media_image6.png 170 143 media_image6.png Greyscale ( claim 9 ); M(L A ) 2 (L B ) 1 ( claims 11-12 ); PNG media_image7.png 116 127 media_image7.png Greyscale wherein R a1 and R c1 are each alkyl groups and R b1 is hydrogen ( claim 13 ); the ligand L A135-1-3 , wherein i is 135, m is 1, X is 1, R E is R 34 , and G is G 3 thus satisfying proviso (i) ( claims 21 and 33 ); the compound Ir(L A135-1-3 )(L C1-I ) ( claim 14 ). Per claim 18 , the host of CBP comprises a carbazole chemical moiety (see structure on pg. 71 of Choi). Per claim 20 , an organic light-emitting device may be considered a consumer product . 07-21-aia AIA Claim s 1-2, 4, 8-9, 11-13, 17-18, 20, and 30 are rejected under 35 U.S.C. 103 as being unpatentable over Ji (US 2018/0138427 A1) in view of Yang (Yang, B. N., and D. M. Shin. "The Synthesis and Properties of Solution Processable a Red Phosphorescent Iridium (III) Complex with Alkyl Group." Journal of Nanoscience and Nanotechnology 16.3 (2016): 2696-2700.) Regarding claims 1-2, 4, 8-9, 11-13, 17, and 30 , Ji teaches an organic light emitting diode having improved performance by including an anode, a cathode, and an organic layer comprising a host and a compound including a ligand L A of Formula (I) (¶ [0015]-[0030] and [0090]). Ji teaches a specific example of the compound in Ir(L b183 ) 2 L A21 (pg. 119). (I): PNG media_image10.png 114 92 media_image10.png Greyscale Ir(L b183 ) 2 L A21 : PNG media_image11.png 215 265 media_image11.png Greyscale Ir(L b183 ) 2 L A21 fails to read on the claimed Formula I as it does not include a 5-membered ring in the location of ring A. However, Ji teaches ring A may be a 5-membered heterocyclic ring including thiophene (¶ [0017] and [0054]). Yang teaches (TMP-HT) 2 Ir(acac), which is an iridium-based organometallic complex for use in an organic light-emitting diode (abstract; Figure 1 on pg. 2697). The (TMP-HT) 2 Ir(acac) comprises an alkyl-substituted thiophene group, wherein the thiophene group increases electron density and the alkyl group has hydrophobic property (abstract). Electron density helps with intramolecular charge transfer, and hydrophobic property is beneficial for solution processes (abstract; second paragraph of Introduction on pg. 2696). (TMP-HT) 2 Ir(acac): PNG media_image3.png 149 86 media_image3.png Greyscale 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 phenyl group in the location of ring A in Ir(L b183 ) 2 L A21 with a hexyl-substituted thiophene group as shown in (TMP-HT) 2 Ir(acac), as taught by Yang. The motivation for doing so would have been to provide a complex with increased electron density and shydrophobic property, as taught by Yang. The modified Ir(L b183 ) 2 L A21 is reproduced below in comparison to the claimed Formula I. modified Ir(L b183 ) 2 L A21 : PNG media_image12.png 413 403 media_image12.png Greyscale Formula I: PNG media_image5.png 173 144 media_image5.png Greyscale The modified Ir(L b183 ) 2 L A21 reads on the claimed Formula I and II ( claims 1 and 8 ) wherein: X 1 to X 8 is C; Y 1’ and Y 2’ are each S; R A is hydrogen, R B is alkyl, R C is alkenyl that join to form a ring ( claim 2 ); and M is Ir. The modified Ir(L b183 ) 2 L A21 satisfies the provisos (ii) and (v) wherein at least one R B comprises alkyl comprising at least 3 carbon atoms, and two R C are joined to form a ring fused to ring C, wherein the ring system comprises at least two rings and comprises a 6-membered ring fused to ring C ( claims 4 and 30 ). Additionally, the modified Ir(L b183 ) 2 L A21 meets the limitations of: PNG media_image13.png 205 217 media_image13.png Greyscale ( claim 9 ); M(L A ) 1 (L B ) 2 ( claims 11-12 ); PNG media_image14.png 205 99 media_image14.png Greyscale wherein Y 1 to Y 8 are each C, and R a and R b are each combinations of hydrogen, alkyl, and deuterium ( claim 13 ). Regarding claim 18 , Ji in view of Yang teach the device including an organic layer comprising a host and the modified Ir(L b183 ) 2 L A21 , as described above with respect to claim 17. Ji in view of Yang fail to specifically teach an example of a host in combination with the modified Ir(L b183 ) 2 L A21 . However, Ji does teach the host may be selected from the compound PNG media_image15.png 149 288 media_image15.png Greyscale , among others (¶ [0097]). 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 use the compound above as a host in the device of Ji in view of Yang, because it would have been choosing from a list of suitable hosts taught by Ji, which would have been a choice from a finite number of identified, predictable solutions the device of Ji in view of Yang and possessing the benefits taught by Ji and Yang. One of ordinary skill in the art would have been motivated to produce additional devices comprising hosts taught by Ji and having the benefits taught by Ji 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 host above has a carbazole chemical moiety. Regarding claim 20 , Ji in view of Yang teach the device including the modified Ir(L b183 ) 2 L A21 , as described above with respect to claim 17. Ji in view of Yang fail to specifically teach a consumer product comprising the device including the modified Ir(L b183 ) 2 L A21 . However, Ji does teach the organic light emitting device may be incorporated into a consumer product (¶ [0030]). 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 incorporate the device including the modified Ir(L b183 ) 2 L A21 into a consumer product , because this would have been combining the prior art elements of Ji according to known methods to yield predictable results of a having improved performance , as taught by Ji. See MPEP 2143.I.(A) . 07-21-aia AIA Claim s 1-2, 4, 8-9, 11-14, 17-18, 20-21, 29, and 33 are rejected under 35 U.S.C. 103 as being unpatentable over Ji (US 2018/0138427 A1) in view of Cho (Cho, Woosum, et al. "Highly efficient, conventional and flexible deep-red phosphorescent OLEDs using ambipolar thiophene/selenophene-phenylquinoline ligand-based Ir (III) complexes." Dyes and Pigments 136 (2017): 390-397.) Regarding claims 1-2, 4, 8-9, 11-14, 17, 21, 29, and 33 , Ji teaches an organic light emitting diode having improved performance by including an anode, a cathode, and an organic layer comprising a host and a compound including a ligand L A of Formula (I) (¶ [0015]-[0030] and [0090]). Ji teaches a specific example of the compound in Ir(L b183 ) 2 L A21 (pg. 119). (I): PNG media_image10.png 114 92 media_image10.png Greyscale Ir(L b183 ) 2 L A21 : PNG media_image11.png 215 265 media_image11.png Greyscale Ir(L b183 ) 2 L A21 fails to read on the claimed Formula I as it does not include a 5-membered ring in the location of ring A. However, Ji teaches ring A may be a 5-membered heterocyclic ring including selenophene (¶ [0017] and [0054]). Cho teaches phosphorescent OLEDs comprising iridium-based complexes including (Se-PQ) 3 Ir (abstract; Scheme 1 on pg. 391). (Se-PQ) 3 Ir contains selenophene which provides the compound with a saturated deep-red emission (Conclusion on pg. 396; second paragraph of Result and discussion on pg. 383-394). (Se-PQ) 3 Ir: PNG media_image8.png 190 169 media_image8.png Greyscale 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 phenyl group in the location of ring A in Ir(L b183 ) 2 L A21 with a selenophene group as shown in (Se-PQ) 3 Ir, as taught by Cho. The motivation for doing so would have been to provide a compound with a saturated deep-red emission, as taught by Cho. The modified Ir(L b183 ) 2 L A21 is reproduced below in comparison to the claimed Formula I. modified Ir(L b183 ) 2 L A21 : PNG media_image16.png 400 400 media_image16.png Greyscale Formula I: PNG media_image5.png 173 144 media_image5.png Greyscale The modified Ir(L b183 ) 2 L A21 reads on the claimed Formula I and II ( claims 1 and 8 ) wherein: X 1 to X 8 is C; Y 1’ is S and Y 2’ is Se; R A is hydrogen, R B is alkyl, R C is alkenyl that join to form a ring ( claim 2 ); and M is Ir. The modified Ir(L b183 ) 2 L A21 satisfies the provisos (i) and (v) wherein Y 2’ is Se, and two R C are joined to form a ring fused to ring C, wherein the ring system comprises at least two rings and comprises a 6-membered ring fused to ring C ( claims 4 and 29 ). Additionally, the modified Ir(L b183 ) 2 L A21 meets the limitations of: PNG media_image13.png 205 217 media_image13.png Greyscale ( claim 9 ); M(L A ) 1 (L B ) 2 ( claims 11-12 ); PNG media_image14.png 205 99 media_image14.png Greyscale wherein Y 1 to Y 8 are each C, and R a and R b are each combinations of hydrogen, alkyl, and deuterium ( claim 13 ); the ligand L A3-73-3 , wherein i is 3, m is 73, X is 3, R E is R 1 , and G is G 3 thus satisfying proviso (ii) ( claims 21 and 33 ); the compound Ir(L A3-73-3 )(L B28 ) ( claim 14 ). Regarding claim 18 , Ji in view of Cho teach the device including an organic layer comprising a host and the modified Ir(L b183 ) 2 L A21 , as described above with respect to claim 17. Ji in view of Cho fail to specifically teach an example of a host in combination with the modified Ir(L b183 ) 2 L A21 . However, Ji does teach the host may be selected from the compound PNG media_image15.png 149 288 media_image15.png Greyscale , among others (¶ [0097]). 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 use the compound above as a host in the device of Ji in view of Yang, because it would have been choosing from a list of suitable hosts taught by Ji, which would have been a choice from a finite number of identified, predictable solutions the device of Ji in view of Cho and possessing the benefits taught by Ji and Cho. One of ordinary skill in the art would have been motivated to produce additional devices comprising hosts taught by Ji and having the benefits taught by Ji 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 host above has a carbazole chemical moiety. Regarding claim 20 , Ji in view of Cho teach the device including the modified Ir(L b183 ) 2 L A21 , as described above with respect to claim 17. Ji in view of Cho fail to specifically teach a consumer product comprising the device including the modified Ir(L b183 ) 2 L A21 . However, Ji does teach the organic light emitting device may be incorporated into a consumer product (¶ [0030]). 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 incorporate the device including the modified Ir(L b183 ) 2 L A21 into a consumer product , because this would have been combining the prior art elements of Ji according to known methods to yield predictable results of a having improved performance , as taught by Ji. See MPEP 2143.I.(A) . 07-21-aia AIA Claim s 1-2, 8-9, 16-18, 20, and 31 are rejected under 35 U.S.C. 103 as being unpatentable over Choi ‘457 (US 2019/0074457 A1) in view of Lamansky (Lamansky, Sergey, et al. "Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes." Journal of the American Chemical Society 123.18 (2001): 4304-4312.) . Regarding claims 1-2, 8-9, 16-18, 20, and 31 , Choi ‘457 teaches an organic light-emitting device including an organometallic compound represented by Formula 1 (¶ [0007]-[0009]). Examples of such devices include the device of Example 14 which includes an anode, an emission layer comprising CBP as a host and Compound 14 as a dopant, and a cathode (¶ [0441]-[0448]; Table 3 on pg. 76; structure of compound on pg. 75). 1: PNG media_image17.png 184 213 media_image17.png Greyscale 14: PNG media_image18.png 170 453 media_image18.png Greyscale Compound 1 fails to read on the claimed Formula I as it does not include a 5-membered ring in the location of CY 2 . However, Choi ‘457 does teach CY 2 may be a C 1 -C 30 heterocyclic group wherein examples thereof include thiophene (¶ [0021] and [0078]). Lamansky teaches iridium complexes for use as dopants in OLEDS (abstract). These complexes are represented by the structure of C^N 2 Ir(acac), wherein C^N may be ppy or thp (see Figs. 1-2). As seen in Fig. 2, the emission of the complex comprising thp is red-shifted compared to the complex comprising ppy. Accordingly, Lamansky teaches replacing phenyl with thiophene in a metal complex causes a red-shifted emission. ppy: PNG media_image19.png 101 76 media_image19.png Greyscale thp: PNG media_image20.png 103 77 media_image20.png Greyscale 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 substituted phenyl of Compound 1 of Choi ‘457 with thiophene as shown in Lamansky’s complex above to red-shift the emission of the modified compound, as taught by Lamansky. The modified Compound 1 is reproduced below in comparison to the claimed Formula I. modified 1: PNG media_image21.png 217 724 media_image21.png Greyscale Formula I: PNG media_image5.png 173 144 media_image5.png Greyscale The modified Compound 1 reads on the claimed Formula I and II ( claims 1 and 8 ) wherein: X 1 to X 8 is C; Y 1’ is O and Y 2’ is S; R A and R B are each hydrogen, R C is a combination of aryl and alkyl ( claim 2 ); and M is Pt. The modified Compound 1 satisfies the provisos (iii) wherein no two R C are joined to form a ring and at least one R C comprises aryl ( claim 31 ). Additionally, the modified Compound 1 meets the limitations of: PNG media_image6.png 170 143 media_image6.png Greyscale ( claim 9 ); the structure of Formula III wherein moiety E is a monocyclic ring comprising a 6-membered carbocyclic ring and moiety F is a polycyclic fused ring structure comprising a 5-membered heterocyclic ring, Z 1 is C and Z 2 is N, K 1 and K 2 are each a direct bond, L 1 is O, L 2 is a single bond, and L 3 is absent, R E represents no substitution and R F is a combination of alkyl and aryl ( claim 16 ). Per claim 18 , the host of CBP comprises a carbazole chemical moiety (see structure on pg. 49 of Choi ‘457). Per claim 20 , an organic light-emitting device may be considered a consumer product . Allowable Subject Matter 07-43-02 Claims 28 and 32 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA), first paragraph, set forth in this Office action and to include 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 claim 28 , the prior art does not teach or suggest a claimed compound, wherein the compound comprises a ligand having a structure of Formula I wherein ring B is selected from the following: PNG media_image22.png 56 63 media_image22.png Greyscale , PNG media_image23.png 87 88 media_image23.png Greyscale , PNG media_image24.png 79 81 media_image24.png Greyscale , PNG media_image25.png 49 55 media_image25.png Greyscale , and PNG media_image26.png 50 51 media_image26.png Greyscale , in combination with the remainder of claim 28. With respect to claim 32, the prior art does not teach or suggest a compound comprising a ligand having a structure of Formula I wherein at least one of X 5 to X 8 is N, in combination with the remainder of claim 32. Formula I: PNG media_image27.png 200 163 media_image27.png Greyscale Choi (US 2019/0326527 A1), cited in the rejection above, is considered the closest prior art of record. Choi teaches an organic light-emitting device having improved luminescent efficiency by including organometallic compound represented by Formula 1, wherein L 1 is represented by Formula 2 (abstract; ¶ [0010] and [0143]-[0144]). Examples of such devices include the device of Example 1, which includes an anode, an emission layer comprising a host of CBP and a dopant of Compound 1, and a cathode (¶ [0279]-[0282]; Table 4 on pg. 71; compound structure on pg. 70) 2: PNG media_image1.png 164 232 media_image1.png Greyscale 1: PNG media_image2.png 138 335 media_image2.png Greyscale Choi teaches CY 21 may be a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group wherein examples thereof include thiophene and furan (¶ [0018] and [0055]). However, Compound 1 fails to read on the limitations of claim 28 as it does not include a group selected from the following: PNG media_image22.png 56 63 media_image22.png Greyscale , PNG media_image23.png 87 88 media_image23.png Greyscale , PNG media_image24.png 79 81 media_image24.png Greyscale , PNG media_image25.png 49 55 media_image25.png Greyscale , and PNG media_image26.png 50 51 media_image26.png Greyscale .. Additionally, Compound 1 fails to read on the limitations of claim 32 as it is not a compound comprising a ligand having a structure of Formula I wherein at least one of X 5 to X 8 is N. Yang (Yang, B. N., and D. M. Shin. "The Synthesis and Properties of Solution Processable a Red Phosphorescent Iridium (III) Complex with Alkyl Group." Journal of Nanoscience and Nanotechnology 16.3 (2016): 2696-2700.), cited in the rejection above, is relevant to the claimed invention. Yang teaches (TMP-HT) 2 Ir(acac), which is an iridium-based organometallic complex for use in an organic light-emitting diode (abstract; Figure 1 on pg. 2697). The (TMP-HT) 2 Ir(acac) comprises an alkyl-substituted thiophene group, wherein the thiophene group increases electron density and the alkyl group has hydrophobic property (abstract). Electron density helps with intramolecular charge transfer, and hydrophobic property is beneficial for solution processes (abstract; second paragraph of Introduction on pg. 2696). (TMP-HT) 2 Ir(acac): PNG media_image3.png 149 86 media_image3.png Greyscale However, Yang fails to teach a group selected from the following: PNG media_image22.png 56 63 media_image22.png Greyscale , PNG media_image23.png 87 88 media_image23.png Greyscale , PNG media_image24.png 79 81 media_image24.png Greyscale , PNG media_image25.png 49 55 media_image25.png Greyscale , and PNG media_image26.png 50 51 media_image26.png Greyscale ., and fails to teach a compound comprising a ligand having a structure of Formula I wherein at least one of X 5 to X 8 is N. Accordingly, Yang fails to remedy the deficiencies of Choi. Cho (Cho, Woosum, et al. "Highly efficient, conventional and flexible deep-red phosphorescent OLEDs using ambipolar thiophene/selenophene-phenylquinoline ligand-based Ir (III) complexes." Dyes and Pigments 136 (2017): 390-397.), cited in the rejection above, is relevant to the claimed invention. Cho teaches phosphorescent OLEDs comprising iridium-based complexes including (Se-PQ) 3 Ir (abstract; Scheme 1 on pg. 391). (Se-PQ) 3 Ir contains selenophene which provides the compound with a saturated deep-red emission (Conclusion on pg. 396; second paragraph of Result and discussion on pg. 383-394). (Se-PQ) 3 Ir: PNG media_image8.png 190 169 media_image8.png Greyscale However, Cho fails to teach a group selected from the following: PNG media_image22.png 56 63 media_image22.png Greyscale , PNG media_image23.png 87 88 media_image23.png Greyscale , PNG media_image24.png 79 81 media_image24.png Greyscale , PNG media_image25.png 49 55 media_image25.png Greyscale , and PNG media_image26.png 50 51 media_image26.png Greyscale ., and fails to teach a compound comprising a ligand having a structure of Formula I wherein at least one of X 5 to X 8 is N. Accordingly, Cho fails to remedy the deficiencies of Choi. Lamansky (Lamansky, Sergey, et al. "Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes." Journal of the American Chemical Society 123.18 (2001): 4304-4312.), cited in the rejection above, is relevant to the claimed invention. Lamansky teaches iridium complexes for use as dopants in OLEDS (abstract). These complexes are represented by the structure of C^N 2 Ir(acac), wherein C^N may be ppy or thp (see Figs. 1-2). As seen in Fig. 2, the emission of the complex comprising thp is red-shifted compared to the complex comprising ppy. Accordingly, Lamansky teaches replacing phenyl with thiophene in a metal complex causes a red-shifted emission. ppy: PNG media_image19.png 101 76 media_image19.png Greyscale thp: PNG media_image20.png 103 77 media_image20.png Greyscale However, Lamansky fails to teach a group selected from the following: PNG media_image22.png 56 63 media_image22.png Greyscale , PNG media_image23.png 87 88 media_image23.png Greyscale , PNG media_image24.png 79 81 media_image24.png Greyscale , PNG media_image25.png 49 55 media_image25.png Greyscale , and PNG media_image26.png 50 51 media_image26.png Greyscale ., and fails to teach a compound comprising a ligand having a structure of Formula I wherein at least one of X 5 to X 8 is N. Accordingly, Lamansky fails to remedy the deficiencies of Choi. Thus there is no prior art, either alone or in combination, which teaches or renders obvious a claimed compound, wherein the compound comprises a ligand having a structure of Formula I wherein ring B is selected from the following: PNG media_image22.png 56 63 media_image22.png Greyscale , PNG media_image23.png 87 88 media_image23.png Greyscale , PNG media_image24.png 79 81 media_image24.png Greyscale , PNG media_image25.png 49 55 media_image25.png Greyscale , and PNG media_image26.png 50 51 media_image26.png Greyscale , in combination with the remainder of claim 28. Thus there is no prior art, either alone or in combination, which teaches or renders obvious a compound comprising a ligand having a structure of Formula I wherein at least one of X 5 to X 8 is N, in combination with the remainder of claim 32 . Conclusion 07-40 AIA Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL . See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a). A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action. 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 on 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: 17/516,647 Page 2 Art Unit: 1786 Application/Control Number: 17/516,647 Page 3 Art Unit: 1786 Application/Control Number: 17/516,647 Page 4 Art Unit: 1786 Application/Control Number: 17/516,647 Page 5 Art Unit: 1786 Application/Control Number: 17/516,647 Page 6 Art Unit: 1786 Application/Control Number: 17/516,647 Page 7 Art Unit: 1786 Application/Control Number: 17/516,647 Page 8 Art Unit: 1786 Application/Control Number: 17/516,647 Page 9 Art Unit: 1786 Application/Control Number: 17/516,647 Page 10 Art Unit: 1786 Application/Control Number: 17/516,647 Page 11 Art Unit: 1786 Application/Control Number: 17/516,647 Page 12 Art Unit: 1786 Application/Control Number: 17/516,647 Page 13 Art Unit: 1786 Application/Control Number: 17/516,647 Page 14 Art Unit: 1786 Application/Control Number: 17/516,647 Page 15 Art Unit: 1786 Application/Control Number: 17/516,647 Page 16 Art Unit: 1786 Application/Control Number: 17/516,647 Page 17 Art Unit: 1786 Application/Control Number: 17/516,647 Page 18 Art Unit: 1786 Application/Control Number: 17/516,647 Page 19 Art Unit: 1786 Application/Control Number: 17/516,647 Page 20 Art Unit: 1786 Application/Control Number: 17/516,647 Page 21 Art Unit: 1786 Application/Control Number: 17/516,647 Page 22 Art Unit: 1786 Application/Control Number: 17/516,647 Page 23 Art Unit: 1786 Application/Control Number: 17/516,647 Page 24 Art Unit: 1786 Application/Control Number: 17/516,647 Page 25 Art Unit: 1786 Application/Control Number: 17/516,647 Page 26 Art Unit: 1786 Application/Control Number: 17/516,647 Page 27 Art Unit: 1786
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