DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Terminal Disclaimer
The terminal disclaimer filed on 04/08/2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of US Patent 12,473,317 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Election/Restrictions
Applicant's election without traverse of species (A2), wherein ring B is a 5-membered ring and ring C is a 6-membered ring, in the reply filed on 11/25/2025 is acknowledged.
Claim 4 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group.
Response to Amendment
The amendment of 04/08/2026 has been entered.
Disposition of claims:
Claims 5 and 19 have been canceled.
Claims 21-22 have been added.
Claim 4 has been withdrawn.
Claims 1-4, 6-18, and 20-22 are pending.
Claims 1, 9-10, 15-17, and 20 have been amended.
The cancellation of claims 5 and 19 obviates the rejections of claims 5 and 19 set forth in the last Office Action.
The Terminal Disclaimer filed on 04/08/2026 obviates the rejections of claims 1-3, 5, 7-12, 14-15, and 17-20 on the ground of nonstatutory double patenting as being unpatentable over claim 1, 15, 17, and 19-20 of US Patent no. 12,473,317.
The amendments of claim 15 has overcome the rejection of claim 15 under 35 U.S.C. 112(b) and the rejection of claim 15 under 35 U.S.C. 112(d) set forth in the last Office Action. The rejections have been withdrawn.
The amendments of claims 1, 9-10, 15-17, and 20 have overcome:
the rejections of claims 1, 3, 5, 7-9, 11-12, and 14-15 under 35 U.S.C. 102(a)(2) as being anticipated by Kwon et al. (US 2022/0348599 A1, hereafter Kwon),
the rejections of claims 13 and 17-18 under 35 U.S.C. 103 as being unpatentable over Kwon et al. (US 2022/0348599 A1),
the rejections of claims 19-20 under 35 U.S.C. 103 as being unpatentable over Kwon et al. (US 2022/0348599 A1) as applied to claims 13 and 17-18 above, further in view of Kai et al. (US 2010/0187977 A1, hereafter Kai),
the rejections of claims 1, 3, 5-9, 11-12, and 14-15 under 35 U.S.C. 103 as being unpatentable over Kwon et al. (US 2022/0348599 A1) in view of Hwang et al. (“Iridium(III) Complexes with Orthometalated Quinoxaline Ligands: Subtle Tuning of Emission to the Saturated Red Color”, Inorg. Chem. 2005, vol. 44, page 1344-1353, hereafter Hwang),
the rejections of claims 1-3, 5, 7-12, and 14-15 under 35 U.S.C. 103 as being unpatentable over Kwon et al. (US 2022/0348599 A1) in view of Acharya et al. (“Effect of Selenium Substitution on Intersystem Crossing in π-Conjugated Donor−Acceptor−Donor Chromophores: The LUMO Matters the Most”, J. Phys. Chem. Letts 2016, vol. 7, page 693-697, hereafter Acharya),
the rejections of claims 1-3, 5, 7-12, and 14-20 under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2015/0236276 A1, hereafter Boudreault) in view of Acharya et al. (“Effect of Selenium Substitution on Intersystem Crossing in π-Conjugated Donor−Acceptor−Donor Chromophores: The LUMO Matters the Most”, J. Phys. Chem. Letts 2016, vol. 7, page 693-697),
the rejection of claim 6 under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2015/0236276 A1) in view of Acharya et al. (“Effect of Selenium Substitution on Intersystem Crossing in π-Conjugated Donor−Acceptor−Donor Chromophores: The LUMO Matters the Most”, J. Phys. Chem. Letts 2016, vol. 7, page 693-697) as applied to claims 1-3, 5, 7-12, and 14-20 above, further in view of Hwang et al. (“Iridium(III) Complexes with Orthometalated Quinoxaline Ligands: Subtle Tuning of Emission to the Saturated Red Color”, Inorg. Chem. 2005, vol. 44, page 1344-1353),
the rejection of claim 13 under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2015/0236276 A1) in view of Acharya et al. (“Effect of Selenium Substitution on Intersystem Crossing in π-Conjugated Donor−Acceptor−Donor Chromophores: The LUMO Matters the Most”, J. Phys. Chem. Letts 2016, vol. 7, page 693-697) as applied to claims 1-3, 5, 7-12, and 14-20 above, further in view of Hou et al. (US 2011/0234089 A1, hereafter Hou).
the rejections of claims 1-3, 5, 7-8, 11-12, 14-15, 17-18, and 20 on the ground of nonstatutory double patenting as being unpatentable over claim 1, 15, 18, and 20 of US Patent no. 12,325,717 (hereafter Patent ‘717) set forth in the last Office Action.
The rejections have been withdrawn.
Response to Arguments
Applicant’s arguments see page 66-69 of the reply filed 04/08/2026 regarding the rejections of claims 1, 3, 5, 7-9, 11-12, and 14-15 under 35 U.S.C. 102(a)(2) as being anticipated by Kwon, the rejections of claims 13 and 17-18 under 35 U.S.C. 103 as being unpatentable over Kwon, the rejections of claims 19-20 under 35 U.S.C. 103 as being unpatentable over Kwon/Kai, the rejections of claims 1, 3, 5-9, 11-12, and 14-15 under 35 U.S.C. 103 as being unpatentable over Kwon/Hwang, the rejections of claims 1-3, 5, 7-12, and 14-15 under 35 U.S.C. 103 as being unpatentable over Kwon/Acharya set forth in the Office Action of 01/08/2026 have been considered.
Applicant argues that the rejections need to be withdrawn in light of the amendment.
The rejections have been withdrawn. The arguments are moot.
Applicant’s arguments see page 70-72 of the reply filed 04/08/2026 regarding the rejections of claims 1-3, 5, 7-12, and 14-20 under 35 U.S.C. 103 as being unpatentable over Boudreault/Acharya, the rejection of claim 6 under 35 U.S.C. 103 as being unpatentable over Boudreault/Acharya/Hwang, the rejection of claim 13 under 35 U.S.C. 103 as being unpatentable over Boudreault/Acharya/Hou set forth in the Office Action of 01/08/2026 have been considered.
Applicant argues that the rejections need to be withdrawn in light of the amendment.
The rejections have been withdrawn. The arguments are moot.
Applicant’s arguments see page 71-72 of the reply filed 04/08/2026 regarding the rejections of claims 1-3, 5, 7-8, 11-12, 14-15, 17-18, and 20 on the ground of nonstatutory double patenting as being unpatentable over claim 1, 15, 18, and 20 of Patent ‘717 set forth in the Office Action of 01/08/2026 have been considered.
Applicant argues that the rejections need to be withdrawn in light of the amendment.
The rejections have been withdrawn. The arguments are moot.
Claim Rejections - 35 USC § 103
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 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.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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.
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.
Claims 1-3, 6-12, 14-15, 17-18, and 20-22 are rejected under 35 U.S.C. 103 as being unpatentable over Ji et al. (US 2018/0138427 A1, hereafter Ji) in view of Boudreault et al. (US 2015/001472 A1, hereafter Boudreault ‘472) and Acharya et al. (“Effect of Selenium Substitution on Intersystem Crossing in π-Conjugated Donor−Acceptor−Donor Chromophores: The LUMO Matters the Most”, J. Phys. Chem. Letts 2016, vol. 7, page 693-697).
Regarding claims 1-3, 6-12, 14-15, 17-18, and 20-22, Ji discloses a compound used as the emitter of an organic light emitting device ([0002], [0016], [0030]), wherein the compound comprising a ligand LA of Formula I ([0016]-[0029]) and teaches more detailed structural formula (the second structural formula in [0077], hereafter Formula A). Ji exemplifies Ligand LA2 ([0082]).
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Ji does not disclose the full structural formula of a complex comprising the Ligand LA2 and a beta diketonate ligand; however, Ji does teach the ligand LA can be coordinated to a metal M ([0027]) and exemplifies Ir as the metal M ([0074]). Ji teaches other ligands can be coordinated to the metal M ([0029]).
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Boudreault ‘472 teaches a compound comprising a beta diketonate ligand of L1 represented by Formula I ([0015]) used as an emitter of an organic light emitting device ([0002]).
Boudreault ‘472 teaches that incorporation of the ligand of Boudreault ‘472 provides narrow emission spectrum, decreased evaporation temperature, and improved device efficiency ([0017]).
Boudreault ‘472 exemplifies ligand LA1 ([0041]). Boudreault ‘472 teaches the ligand LA1 can be used to coordinate an Ir metal with phenyl pyridine based ligand with 1:2 ligand ratio (Compound 83 in [0090]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the ligand LA1 of Ji by incorporating it into an Ir complex with the ligand LA1 of Boudreault ‘472 with ligand ratio of 2:1, as taught by Ji and Boudreault ‘472.
The motivation of doing so would have been to provide narrow emission spectrum, decreased evaporation temperature, and improved device efficiency, based on the teaching of Boudreault ‘472.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Each substitution of the metal M and the ancillary ligand in the compound of Ji would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Compound of Ji as modified by Boudreault ‘472.
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The resultant compound has a sulfur atom at the position corresponding to X of the Formula A of Ji. However, Ji does teach that X of the Formula A of Ji can be Se ([0069]).
Acharya teaches that selenium has larger atomic radius, larger dipole moment, larger polarizability than sulfur such that band gap and optical properties can be tuned by replacing sulfur with selenium (page 693, col. 1, lines 10-16).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Ji as modified by Boudreault ‘472 by substituting the sulfur atom at the position corresponding to X with selenium, as taught by Ji and Acharya.
The motivation of doing so would have been to provide larger atomic radius, larger dipole moment, larger polarizability, and tunability of band gap and optical properties, based on the teaching of Acharya.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Both S and Se are alternative options for the variable X of Formula A of Ji. Substitution of S with Se at the position X would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Ji as modified by Boudreault ‘472 and Acharya, meeting all the limitations of claims 1-3, 6-12, 14-15, and 21-22.
Ji in view of Boudreault ‘472 and Acharya does not disclose a specific organic light emitting device comprising the Compound of Ji as modified by Boudreault ‘472; however, Boudreault does teach that the compound of Boudreault can be used as the emitter of an organic light emitting device ([0002]). Boudreault teaches the structure of the organic light emitting device comprising an anode, an emissive layer (a host and a dopant), and a cathode ([0030, [0096]]). Boudreault exemplifies a carbazole compound as the host ([0097]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound Ji as modified by Boudreault ‘472 by incorporating it as the emissive dopant with a carbazole compound as the host in the emissive layer of an organic light emitting device having structure of an anode, an emissive layer, and a cathode, as taught by Ji.
The motivation of doing so would have been to provide an organic light emitting device, based on the teaching of Ji.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the emissive dopants and the hosts of Ji in the device of Ji would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Ji as modified by Boudreault ‘472 and Acharya comprising an anode, an emissive layer (a carbazole compound as a host and Compound of Ji as modified by Boudreault ‘472 and Acharya as a dopant), and a cathode, meeting all the limitations of claims 17-18.
Ji in view of Boudreault ‘472 and Acharya does not disclose a specific consumer product comprising the Organic light emitting device of Ji as modified by Boudreault ‘472 and Acharya; however, Ji does teach that the OLED of Ji can be incorporated into a consumer product ([0095], [0030]) including a flat panel display ([0044]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Organic light emitting device of Ji as modified by Boudreault ‘472 and Acharya by incorporating it into a consumer product, as taught by Ji.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the OLEDs of Ji in a flat panel display of Ji would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides a consumer product (i.e. flat panel display) comprising the Organic light emitting device of Ji as modified by Boudreault ‘472 and Acharya, meeting all the limitations of claims 20.
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Ji et al. (US 2018/0138427 A1) in view of Boudreault et al. (US 2015/001472 A1) and Acharya et al. (“Effect of Selenium Substitution on Intersystem Crossing in π-Conjugated Donor−Acceptor−Donor Chromophores: The LUMO Matters the Most”, J. Phys. Chem. Letts 2016, vol. 7, page 693-697) as applied to claims 1-3, 6-9, 11-12, 14, 17-18, and 20-22 above, further in view of Kwong et al. (US 2008/0261076 A1, hereafter Kwong).
Regarding claim 16, the Compound of Ji as modified by Boudreault ‘472 and Acharya reads on all the features of claim 1 as outlined above.
The compound has similar structure as Applicant’s compound
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in claim 16. The first difference is that the methyl group at the position corresponding to RB of Formula A of Ji is required to be 2,2-dimethylpropyl; however, Ji does teach RB can be an alkyl ([0080]) and exemplifies 2,2-dimethylpyropyl as the alkyl group ([0047]).
The second difference is that the hydrogen at the position corresponding to RC of Formula A of Ji (i.e. the hydrogen substituted to the Z8 and Z10 carbon atoms) are required to be methyl; however, Ji does teach that RC can be alkyl ([0080]) and exemplifies methyl as the alkyl ([0047]).
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Kwong teaches dimethyl substituted benzene of an Ir complex provides lower sublimation temperature, higher efficiency, and narrower emission as compared to the compound have no dimethyl groups (compare Compound 1 with Comp. Ex. 4 and Compound 22 in Comp. Ex. 5 ([0052] and Table 2).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Ji as modified by Boudreault ‘472 and Acharya by substituting 1) the methyl group at the position corresponding to RB of Formula A of Ji with 2,2-dimethylpropyl, and 2) the hydrogen at the position corresponding to RC of Formula A of Ji with methyl, as taught by Ji and Kwong.
The motivation of doing so would have been to provide lower sublimation temperature, higher efficiency, and narrower emission as compared to the compound have no dimethyl groups based on the teaching of Kwong.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of exemplified substituent groups in the compound of Formula A of Ji would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Compound of Ji as modified by Boudreault ‘472, Acharya, and Kwong which has identical structure as
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.
Claims 1-3, 6-9, 11, 13-14, and 21-22 are rejected under 35 U.S.C. 103 as being unpatentable over Ji et al. (US 2018/0138427 A1) in view of Hou et al. (US 2011/0234089 A1, hereafter Hou) and Acharya et al. (“Effect of Selenium Substitution on Intersystem Crossing in π-Conjugated Donor−Acceptor−Donor Chromophores: The LUMO Matters the Most”, J. Phys. Chem. Letts 2016, vol. 7, page 693-697).
Regarding claims 1-3, 6-9, 11, 13-14, and 21-22, Ji discloses a compound used as the emitter of an organic light emitting device ([0002], [0016], [0030]), wherein the compound comprising a ligand LA of Formula I ([0016]-[0029]) and teaches more detailed structural formula (the second structural formula in [0077], hereafter Formula A). Ji exemplifies Ligand LA2 ([0082]).
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Ji does not disclose the full structural formula of a complex comprising the Ligand LA2 and a beta diketonate ligand; however, Ji does teach the ligand LA can be coordinated to a metal M ([0027]) and exemplifies Ir as the metal M ([0074]). Ji teaches other ligands can be coordinated to the metal M ([0029]).
Hou discloses a complex compound represented by Formula (1) ([0026]), wherein the compound necessarily comprises a ligand represented by
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. Hou exemplifies a N,N’-diisopropylbenzamidine (dipba) ligand
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(the right ligand of formula (5) in [0155]).
Hou teaches that the compound of Hou provides low voltage and high efficiency ([0191]) and higher HOMO and smaller HOMO-LUMO gap as compared to an acac ligand (Table 2, [0293]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the ligand LA1 of Ji by incorporating it into an Ir complex with the dipba ligand of Hou with the ligand ratio of 2:1, as taught by Ji and Hou.
The motivation of doing so would have been to provide low voltage and high efficiency and higher HOMO and smaller HOMO-LUMO gap based on the teaching of Hou.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the known ancillary ligands in the compound of Boudreault would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Compound of Kwon as modified by Acharya and Hou.
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The resultant compound has a sulfur atom at the position corresponding to X of the Formula A of Ji. However, Ji does teach that X of the Formula A of Ji can be Se ([0069]).
Acharya teaches that selenium has larger atomic radius, larger dipole moment, larger polarizability than sulfur such that band gap and optical properties can be tuned by replacing sulfur with selenium (page 693, col. 1, lines 10-16).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Ji as modified by Boudreault ‘472 by substituting the sulfur atom at the position corresponding to X with selenium, as taught by Ji and Acharya.
The motivation of doing so would have been to provide larger atomic radius, larger dipole moment, larger polarizability, and tunability of band gap and optical properties, based on the teaching of Acharya.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Both S and Se are alternative options for the variable X of Formula A of Ji. Substitution of S with Se at the position X would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Ji as modified by Hou and Acharya.
Conclusion
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SEOKMIN JEON whose telephone number is (571)272-4599. The examiner can normally be reached Monday - Friday 8:30am to 5:00pm EST.
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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.
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/SEOKMIN JEON/Primary Examiner, Art Unit 1786
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