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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 04/16/2026 has been entered.
Terminal Disclaimer
The terminal disclaimer filed on 12/29/2025 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of the US Patent no. 12,369,488 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Election/Restrictions
Applicant's election of (A1) compounds where metal M is Ir, and (B3) formula II is fused to X3 and X4, and each of X1 to X4 is C, in the reply filed on 6/26/2025 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
In the Office Action of 07/29/2025, the Examiner partially withdraws the requirement of election of species to identify atoms at X1 through X4. Applicant’s election is equated with (A1) compounds where metal M is Ir, and (B3) formula II is fused to X3 and X4, and each of X1 to X4 is C or N.
Claims 16 and 18 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group.
Response to Amendment
The amendment of 04/16/2026 has been entered.
Disposition of claims:
Claims 10 and 14-15 have been canceled.
Claims 21-23 have been added.
Claims 1-9, 11-13, and 16-23 are pending.
Claims 16 and 18 have been withdrawn.
Claims 1, 3, 5, and 17-20 have been amended.
The cancelation of claims 10 and 14-15 obviate the rejections of claims 10 and 14-15 set forth in the last Office Action.
Response to Arguments
Applicant’s arguments see page 65-67 of the reply filed 04/16/2026 regarding the rejections of claims 1-2, 4, 6-7, 9, 11-14, and 17-20 under 35 U.S.C. 103 as being unpatentable over Adamovich et al. (US 2019/0280213 A1, hereafter Adamovich) in view of Wang et al. (“Highly efficient electroluminescent materials based on fluorinated organometallic iridium compounds” Appl. Phys. Lett. 2001, vol. 79, page 449-451, hereafter Wang) and Kim et al. (US 2008/0194853 A1, hereafter Kim) set forth in the Office Action of 12/22/2025 have been considered.
Applicant argues that the rejection based on Adamovich, Wang, and Kim should be withdrawn.
Respectfully, the Examiner does not agree.
The rejections refer to the Compound of Adamovich as modified by Wang and Kim which has identical structure as Compound of Adamovich as modified by Wang (see the structure below) except the all the hydrogen atoms in the left ligand including the hydrogen atoms bonded to the benzene ring of the benzothieno group (i.e. the first fused ring moiety) and the rings A and B are substituted with deuterium.
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The Compound of Adamovich as modified by Wang and Kim reads on the conditions (i) - X1 is carbon and the R2 bonding to said carbon is deuterium, because the compound has deuterium atoms which replace all the hydrogen atoms in the left ligand of the Compound of Adamovich as modified by Wang as outlined above. Thus, the rejections are maintained.
Applicant’s arguments see page 67-69 of the reply filed 04/16/2026 regarding the rejections of claims 1-4, 6-15, 17-18, and 20 under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 2021/0355148 A1, hereafter Choi) in view of Kim et al. (US 2008/0194853 A1) and Zhang et al. (US 20200354391 A1, hereafter Zhang) set forth in the Office Action of 12/22/2025 have been considered.
Applicant argues that Choi, Kim, and Zhang taken alone or in any fair combination, do not teach or suggest the instantly claimed subject matter in which at least one of conditions i) to iv) is true.
Respectfully, the Examiner does not agree.
The rejections refer to Compound of Choi as modified by Kim, and Zhang (1) to (3).
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The Compound of Choi as modified by Kim and Zhang (3) has identical structure as
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(the 11th compound on page 61).
Each of the compounds reads on the conditions (i) - X1 is carbon and the R2 bonding to said carbon is deuterium. Thus, the rejections are maintained.
Applicant further argues that a person of ordinary skill in the art at the time of the effective filing date of the present application, in view of Choi’s Compound 6 and 9, would not have combined Choi, which relates to a 5-membered ring that is directly fused to 6-membered ring, with Zhang, which relates to structurally distinct compounds, namely a 6-membered ring that is directly fused to 6-membered ring, with any reasonable expectation of achieving the same benefits from deuteration of a polycyclic fused ring system having 5-membered ring that is directly fused to 6-membered ring (page 69).
Respectfully, the Examiner does not agree.
Choi discloses a compound (Formula 1) used for an organic light emitting device ([0005]) wherein the ring CY1 of the Formula 1 can be Formula CY1-4 or CY1-5 ([0007]). Choi exemplifies Compounds 6 and 9 ([0169]).
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The Compound 6 (or 9) has similar structure as Applicant’s Formula I. The only difference between two compounds is that the hydrogen atom of the Compound 6 (or 9) corresponding to the R11 of Formulas CY1-4 or CY1-5 substituted to the carbon at the position corresponding to X11 (i.e. the hydrogen pointed by an arrow in the figure above) is required to be deuterium; however, Choi does teach that R11 can be deuterium ([0013]).
Because Choi teaches that the substituent at R11 can be deuterium, the only knowledge that an ordinary skill in the art would have relied upon from Kim is the advantage of deuterium as compared to hydrogen.
Kim teaches that substitution of hydrogen with deuterium provides lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability ([0021]-[0022]).
The advantages of deuterium cited in the rejections are fundamental and the benefits of deuterium as compared to hydrogen exist regardless of the difference in the backbone structure of 5- or 6-membered ring that Applicant argued.
Zhang further teaches the benefits of the substitution of the deuterium atom at the position corresponding to the carbon at X1 of Formula (I) of the instant claim.
Zhang teaches that substitution of the deuterium atom at the position 3 of the isoquinoline ring provides lower voltage, higher power efficiency, and longer lifetime to the organic light emitting device when the compound is used as the emitter of the device, otherwise same (Compare Embodiment 1 comprising Compound Ir(La126)2(Lb101) vs. Comparative Example 1 comprising Compound RD1 in Tables 1 and 2).
Choi and Zhang are in the similar field of art, red phosphorescent Ir complex. Ir complex of Zhang having an isoquinoline ligand has a great similarity in structure and emission color as the Ir complex of Choi such that an ordinary skill in the art would expect similar advantages in the complex of Choi when the substitution of hydrogen with deuterium at the position 3 of the pyridine ring coordinating to the Ir occurs.
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound 6 (or 9) of Choi by substituting the hydrogen at the position corresponding to the R11 of Formulas CY1-5 (or CY1-4) of Choi with deuterium, as taught by Choi, Kim and Zhang.
For at least the reason outlined above, Applicant’s arguments are not found persuasive. The rejections are maintained.
Applicant’s arguments see page 69-71 of the reply filed 04/16/2026 regarding the rejections of claims 1-7, 9, and 11-14 under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 2021/0355148 A1) in view of Wang et al. (“Highly efficient electroluminescent materials based on fluorinated organometallic iridium compounds” Appl. Phys. Lett. 2001, vol. 79, page 449-451) and Kim et al. (US 2008/0194853 A1) set forth in the Office Action of 12/22/2025 have been considered.
Applicant argues that Choi, Wang, and Kim taken alone or in any fair combination, do not teach or suggest the instantly claimed subject matter in which at least one of conditions i) to iv) is true.
Respectfully, the Examiner does not agree.
The rejections refer to Compound of Choi as modified by Wang and Kim which has identical structure as Compound of Choi as modified by Wang (see the structure below) except the all the hydrogen atoms in the left ligand are substituted with deuterium.
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The Compound of Choi as modified by Wang and Kim reads on the conditions (i) - X1 is carbon and the R2 bonding to said carbon is deuterium. Thus, the rejections are maintained.
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 1-4, 6-7, 9, 11-13, 17, and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Adamovich et al. (US 2019/0280213 A1, hereafter Adamovich) in view of Wang et al. (“Highly efficient electroluminescent materials based on fluorinated organometallic iridium compounds” Appl. Phys. Lett. 2001, vol. 79, page 449-451, hereafter Wang) and Kim et al. (US 2008/0194853 A1, hereafter Kim).
Regarding claims 1-4, 6-7, 9, 11-13, 17, and 19-20, Adamovich discloses a composition (“second composition”) used as the emissive layer material of an organic light emitting device, wherein the composition comprises a first compound of Formula I as a host and a second compound of Formulas III, wherein R represents Formula IV ([0020]-[0024]).
Adamovich exemplifies a compound as the second compound ([0093], the 9th compound on page 17, hereafter Compound p17-9).
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The Compound p17-9 does not have a fluoro group at the position corresponding to RA of Formula III of Adamovich; however, Adamovich does teach that RA can be a general substituent ([0020]). Adamovich exemplifies fluorine as one of more preferred substituents ([0064]). Adamovich exemplifies a compound comprising a structure of
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(the last compound on page 19).
Wang teaches that conversion of C-H bond to C-F bond provides reduced radiationless deactivation, enhanced photoluminescence efficiency, better sublimation, minimized self-quenching, and enhanced electron mobility (page 450, col. 1, par. 1).
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 p17-9 of Adamovich by substituting a fluoro group to the benzene ring corresponding to the ring A of Formula III of Adamovich, as taught by Adamovich and Wang.
The motivation of doing so would have been to provide reduced radiationless deactivation, enhanced photoluminescence efficiency, better sublimation, minimized self-quenching, and enhanced electron mobility, based on the teaching of Wang.
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). Fluorine is specifically-exemplified and preferred substituent at the position corresponding to RA of Formula III. The substitution of hydrogen with fluorine at the position corresponding to RA of Formula III 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 Adamovich as modified by Wang.
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The left ligand of the Compound of Adamovich as modified by Wang is not substituted by deuterium; however, Adamovich does teach the R groups of the first ligand of Adamovich can be deuterium ([0021], [0061]).
Kim discloses a deuterated Ir complex used as the luminescent material of an organic light emitting device ([0001]). Kim exemplifies the all the hydrogen atoms substituted to the aromatic and heteroaromatic rings of the left ligand of the complex are substituted by deuterium ([0045]).
Kim teaches that substitution of hydrogen with deuterium provides lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability ([0021]-[0022]).
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 Adamovich as modified by Wang by substituting all the hydrogen atoms substituted to the left ligand of the complex with deuterium, as taught by Adamovich and Kim.
The motivation of doing so would have been to provide lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability base on the teaching of Kim.
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 hydrogen as the R groups of the Formulas III and IV of Adamovich 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 Adamovich as modified by Wang and Kim which has identical structure as Compound of Adamovich as modified by Wang except the all the hydrogen atoms in the left ligand including the hydrogen atoms bonded to the benzene ring of the benzothieno group (i.e. the first fused ring moiety) and the rings A and B are substituted with deuterium, meeting all the limitations of claims 1-4, 6-7, 9, 11-13, and 19.
Adamovich in view of Wang and Kim does not disclose a specific organic light emitting device comprising the Compound of Adamovich as modified by Wang and Kim; however, Adamovich does teach that the second compound of Adamovich can be used as the emitter of an organic light emitting device ([0024], [0015]).
Adamovich teaches the structure of the organic light emitting device comprising an anode, an emissive layer (Compound H1 as a host, a second compound of Adamovich), and a cathode ([0156]). The Compound H1 of Adamovich comprises carbazole.
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 Adamovich as modified by Wang and Kim by incorporating it as the emitter of an organic light emitting device, as taught by Adamovich.
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 second compounds of Adamovich 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 Adamovich as modified by Wang and Kim comprising an anode, an emissive layer (Compound H1 as a host, and Compound of Adamovich as modified by Wang and Kim as an emitter), and a cathode, meeting all the limitations of claim 17.
Adamovich does not disclose a specific consumer product comprising the Organic light emitting device of Adamovich as modified by Wang and Kim; however, Adamovich does teach a consumer product comprising the organic light emitting device of Adamovich ([0024]).
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 Adamovich as modified by Wang and Kim by incorporating it into a consumer product, as taught by Adamovich.
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 organic light emitting devices in a consumer product 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 comprising the Organic light emitting device of Adamovich as modified by Wang and Kim, meeting all the limitations of claim 20.
Claims 1-4, 6-9, 11-13, 17, and 20-23 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 2021/0355148 A1, hereafter Choi) in view of Kim et al. (US 2008/0194853 A1) and Zhang et al. (US 20200354391 A1, hereafter Zhang).
Regarding claims 1-4, 6-9, 11-13, 17, and 20-22, Choi discloses a compound (Formula 1) used for an organic light emitting device ([0005]) wherein the ring CY1 of the Formula 1 can be Formula CY1-4 or CY1-5 ([0007]). Choi exemplifies Compounds 6 and 9 ([0169]).
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The Compound 6 (or 9) has similar structure as Applicant’s Formula I. The only difference between two compounds is that the hydrogen atom of the Compound 6 (or 9) corresponding to the R11 of Formulas CY1-4 or CY1-5 substituted to the carbon at the position corresponding to X11 (i.e. the hydrogen pointed by an arrow in the figure above) is required to be deuterium; however, Choi does teach that R11 can be deuterium ([0013]).
Kim discloses a deuterated Ir complex used as the luminescent material of an organic light emitting device ([0001]).
Kim teaches that substitution of hydrogen with deuterium provides lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability ([0021]-[0022]).
Zhang discloses an Ir complex comprising a phenyl isoquinoline ligand used for an organic light emitting device ([0018], [0164]).
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Zhang teaches that substitution of the deuterium atom at the position 3 of the isoquinoline ring provides lower voltage, higher power efficiency, and longer lifetime to the organic light emitting device when the compound is used as the emitter of the device, otherwise same (Compare Embodiment 1 comprising Compound Ir(La126)2(Lb101) vs. Comparative Example 1 comprising Compound RD1 in Tables 1 and 2). Choi and Zhang are in the similar field of art, red phosphorescent Ir complex. Ir complex of Zhang having an isoquinoline ligand has a great similarity in structure and emission color as the Ir complex of Choi such that an ordinary skill in the art would expect similar advantages in the complex of Choi when the substitution of hydrogen with deuterium at the position 3 of the pyridine ring coordinating to the Ir occurs.
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 6 (or 9) of Choi by substituting the hydrogen at the position corresponding to the R11 of Formulas CY1-5 (or CY1-4) of Choi with deuterium, as taught by Choi, Kim and Zhang.
The motivation of doing so would have been to provide lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability based on the teaching of Kim, and provide lower voltage, higher power efficiency, and longer lifetime to the organic light emitting device comprising the compound based on the teaching of Zhang.
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 hydrogen with deuterium at R11 of Formulas CY-5 and CY-6 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 Choi as modified by Kim and Zhang (1), meeting all the limitations of claims 1-4, 6-9, and 11-13.
The modification provides Compound of Choi as modified by Kim and Zhang (2), meeting all the limitations of claims 1-4, 6-7, 9, 11-13, and 21-22.
Choi does not disclose a specific organic light emitting device comprising the Compound of Choi as modified by Kim and Zhang; however, Choi does teach that the compound of Choi can be used as the dopant of the emissive layer of an organic light emitting device ([0029]-[0030]).
Choi teaches the structure of the organic light emitting device comprising an anode, an emissive layer (Compound H52 as a host, a compound of Choi as a dopant), and a cathode (Example 1 in [0474]-[0477]). The Compound H52 of Choi comprises carbazole ([0477]).
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 Choi as modified by Kim and Zhang by incorporating it as the emitter of an organic light emitting device, as taught by Choi.
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 compounds of Choi in the device of Choi 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 Choi as modified by Kim and Zhang comprising an anode, an emissive layer (a carbazole Compound H52 of Choi as a host, and Compound of Choi as modified by Kim and Zhang as a dopant), and a cathode, meeting all the limitations of claim 17.
Choi does not disclose a specific consumer product comprising the Organic light emitting device of Choi as modified by Kim and Zhang; however, Choi does teach that the organic light emitting device can be incorporated into a consumer product such as an illumination device ([0246]).
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 Choi as modified by Kim and Zhang by incorporating it into a consumer product, as taught by Choi.
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 organic light emitting devices in a consumer product 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 comprising the Organic light emitting device of Choi as modified by Kim and Zhang, meeting all the limitations of claim 20.
Regarding claim 23, Choi discloses a compound (Formula 1) used for an organic light emitting device ([0005]) wherein the ring CY1 of the Formula 1 can be Formula CY1-4 ([0007]). Choi exemplifies Compound 9 ([0169]).
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The Compound 9 of Choi has similar structure as Applicant’s specific embodiment of claim 15,
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(the 11th compound on page 61).
The difference between two compounds is: 1) the phenyl at the position corresponding to CY12 is required to be biphenyl, 2) the hydrogen substituted to the carbon at the position corresponding to X15 is required to be methyl, 3) the hydrogen substituted to the carbon at the position corresponding to X11 is required to be deuterium, 4) the methyl group at the position corresponding to R23 is required to be t-butyl, and 5) the 1,1-dimehtyl-propyl group at the positions corresponding to R30a and R30b are each required to be 1-ethyl-1-methyl-propyl.
However, Choi does teach that: 1) the phenyl at the position corresponding to CY12 can be biphenyl ([0087], Formula 10-60); 2) the hydrogen substituted to the carbon at the position corresponding to X15 can be methyl (i.e. R15 at position X15 can be -CH3 in [0085]); 3) the hydrogen substituted to the carbon at the position corresponding to X11 can be deuterium (i.e. R11 at position X11 can be deuterium in [0085]); 4) the methyl group at the position corresponding to R23 can be t-butyl (see example compounds including at least compound 6 in [0169]); and 5) the 1,1-dimehtyl-propyl group at the positions corresponding to R30a and R30b can be 1-ethyl-1-methyl-propyl (see example compounds including at least compound 1 in [0169]).
Kim discloses a deuterated Ir complex used as the luminescent material of an organic light emitting device ([0001]).
Kim teaches that substitution of hydrogen with deuterium provides lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability ([0021]-[0022]).
Zhang discloses an Ir complex comprising a phenyl isoquinoline ligand used for an organic light emitting device ([0018], [0164]).
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Zhang teaches that substitution of the deuterium atom at the position 3 of the isoquinoline ring provides lower voltage, higher power efficiency, and longer lifetime to the organic light emitting device when the compound is used as the emitter of the device, otherwise same (Compare Embodiment 1 comprising Compound Ir(La126)2(Lb101) vs. Comparative Example 1 comprising Compound RD1 in Tables 1 and 2). Choi and Zhang are in the similar field of art, red phosphorescent Ir complex. Ir complex of Zhang having an isoquinoline ligand has a great similarity in structure and emission color as the Ir complex of Choi such that an ordinary skill in the art would expect similar advantages in the complex of Choi when the substitution of hydrogen with deuterium at the position 3 of the pyridine ring coordinating to the Ir occurs.
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 9 of Choi by substituting 1) the phenyl at the position corresponding to CY12 with biphenyl; 2) the hydrogen substituted to the carbon at the position corresponding to X15 with methyl; 3) the hydrogen substituted to the carbon at the position corresponding to X11 with deuterium; 4) the methyl group at the position corresponding to R23 with t-butyl; and 5) the 1,1-dimehtyl-propyl group at the positions corresponding to R30a and R30b with 1-ethyl-1-methyl-propyl, as taught by Choi, Kim, and Zhang
The motivation of doing so would have been to provide lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability based on the teaching of Kim, and provide lower voltage, higher power efficiency, and longer lifetime to the organic light emitting device comprising the compound based on the teaching of Zhang.
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 biphenyl at the position corresponding to CY12; 2) the methyl substituted to the carbon at the position corresponding to X15; 3) the deuterium substituted to the carbon at the position corresponding to X11; 4) the t-butyl group at the position corresponding to R23; and 5) the 1-ethyl-1-methyl-propyl group at the positions corresponding to R30a and R30b are each specifically exemplified substituent groups. Each substitution among the exemplified substituent groups 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 Choi as modified by Kim and Zhang (3) which has identical structure as
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(the 11th compound on page 61).
Claims 1-4, 6-7, 9, and 11-13 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 2021/0355148 A1) in view of Wang et al. (“Highly efficient electroluminescent materials based on fluorinated organometallic iridium compounds” Appl. Phys. Lett. 2001, vol. 79, page 449-451) and Kim et al. (US 2008/0194853 A1).
Regarding claims 1-4, 6-7, 9, and 11-13, Choi discloses a compound (Formula 1) used for an organic light emitting device ([0005]) wherein the ring CY1 of the Formula 1 can be Formula CY1-5 ([0007]). Choi exemplifies Compound 6 ([0169]).
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The naphthalene ring of the left ligand of the Compound 6 of Cho (i.e. the part enclosed by a dashed circle in the figure above) is not a fluoro naphthalene; however, Choi does teach that R21 and R22 of Formula 1 can be hydrogen, alkyl, or fluorine ([0013]) and exemplifies Compound 16 ([0169]), wherein the naphthalene ring is a fluoro naphthalene
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.
Wang teaches that conversion of C-H bond to C-F bond provides reduced radiationless deactivation, enhanced photoluminescence efficiency, better sublimation, minimized self-quenching, and enhanced electron mobility (page 450, col. 1, par. 1).
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 6 of Choi by substituting the t-butyl naphthalene ring with a fluoro naphthalene ring, as taught by Choi and Wang.
The motivation of doing so would have been to provide reduced radiationless deactivation, enhanced photoluminescence efficiency, better sublimation, minimized self-quenching, and enhanced electron mobility, based on the teaching of Wang.
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 t-butyl naphthalene and fluoro naphthalene are specific examples of the bottom ring of the ligand of Formula 1 of Choi. The substitution of the naphthalene ring with a fluoro naphthalene ring in the compound of Formula 1 of Choi 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 Choi as modified by Wang.
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The left ligand of the Compound of Choi as modified by Wang is not deuterated; however, Choi does teach that the hydrogen substituted to the R groups of the left ligand of Formula 1 can be deuterium ([0007]-[0028]).
Kim discloses a deuterated Ir complex used as the luminescent material of an organic light emitting device ([0001]). Kim exemplifies the all the hydrogen atoms substituted to the aromatic and heteroaromatic rings of the left ligand of the complex are substituted by deuterium ([0045]).
Kim teaches that substitution of hydrogen with deuterium provides lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability ([0021]-[0022]).
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 Choi as modified by Wang by substituting all the hydrogen atoms substituted to the aromatic and heteroaromatic rings of the left ligand of the complex with deuterium, as taught by Choi, Wang, and Kim.
The motivation of doing so would have been to provide lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability base on the teaching of Kim.
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 hydrogen with deuterium at the substituent positions of Formula 1 of Choi 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 Choi as modified by Wang and Kim which has identical structure as Compound of Choi as modified by Wang except the all the hydrogen atoms in the left ligand including the hydrogen atoms bonded to the naphthalene ring are substituted with deuterium.
Claims 1-9, 11-13, 17, and 19-22 are rejected under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2019/0248818 A1, hereafter Boudreault) in view of Kim et al. (US 2008/0194853 A1) and Zhang et al. (US 20200354391 A1).
Regarding claims 1-9, 11-13, 17, and 19-20, Boudreault discloses a compound comprising a first ligand LA of Formula I and used for an organic light emitting device ([0015]-[0024]) and exemplifies Compound C3086 ([0176]).
Boudreault exemplifies an organic light emitting device comprising an anode, an emissive layer (Compound C3086 as an emitter and a host), and a cathode ([0190]).
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In the Compound of C3086 of Boudreault, the substituent at the position corresponding to RB of Formula I (i.e. the position pointed by an arrow in the figure above) is not deuterium; however, Boudreault does teach RB of the first ligand of Boudreault can be deuterium ([0023]).
Kim discloses a deuterated Ir complex used as the luminescent material of an organic light emitting device ([0001]).
Kim teaches that substitution of hydrogen with deuterium provides lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability ([0021]-[0022]).
Zhang discloses an Ir complex comprising a phenyl isoquinoline ligand used for an organic light emitting device ([0018], [0164]).
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Zhang teaches that substitution of the deuterium atom at the position 3 of the isoquinoline ring provides lower voltage, higher power efficiency, and longer lifetime to the organic light emitting device when the compound is used as the emitter of the device, otherwise same (Compare Embodiment 1 comprising Compound Ir(La126)2(Lb101) vs. Comparative Example 1 comprising Compound RD1 in Tables 1 and 2). Boudreault and Zhang are in the similar field of art, red phosphorescent Ir complex. Ir complex of Zhang having an isoquinoline ligand has a great similarity in structure and emission color as the Ir complex of Boudreault such that an ordinary skill in the art would expect similar advantages in the complex of Boudreault when the substitution of hydrogen with deuterium at the position 3 of the pyridine ring coordinating to the Ir occurs.
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 C3086 of Boudreault by substituting the hydrogen atoms at the position corresponding to RB of Formula I of Boudreault with deuterium, as taught by Boudreault, Kim, and Zhang.
The motivation of doing so would have been to provide lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability based on the teaching of Kim, and provide lower voltage, higher power efficiency, and longer lifetime to the organic light emitting device comprising the compound based on the teaching of Zhang.
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 hydrogen as the RB groups of the Formulas I and II of Boudreault 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 Boudreault as modified by Kim and Zhang, meeting all the limitations of claims 1-9, 11-13, and 19.
The modification also provides Organic light emitting device of Boudreault as modified by Kim and Zhang comprising an anode, an emissive layer (Compound of Boudreault as modified by Kim and Zhang as an emitter and a host), and a cathode, meeting all the limitations of claim 17.
Boudreault does not disclose a specific consumer product comprising the Organic light emitting device of Boudreault as modified by Kim and Zhang; however, Boudreault does teach that the organic light emitting device can be incorporated into a consumer product such as an illumination device ([0029], [0042]).
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 Boudreault as modified by Kim and Zhang by incorporating it into a consumer product, as taught by Boudreault.
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 organic light emitting devices in a consumer product 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 comprising the Organic light emitting device of Boudreault as modified by Kim and Zhang, meeting all the limitations of claim 20.
Regarding claims 21-22, the Compound of Boudreault as modified by Kim and Zhang reads on all the features of claim 1 as outlined above.
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The Compound of Boudreault as modified by Kim and Zhang has similar structure as Applicant’s compound having Formula 37
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, wherein R3 is RH1
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and G1 is G18
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. The only difference is the hydrogen atom at the position corresponding to RC of Formula II of Boudreault (i.e. the position pointed by an arrow in the figure above) is required to be a methyl group; however, Boudreault does teach that RC can be alkyl ([0023]) and exemplifies a ligand wherein the RC is a methyl (R3 is RB1 in LA2 in [0099]-[0100]).
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 Boudreault as modified by Kim and Zhang by substituting the hydrogen atom at the position corresponding to RC of Formula II of Boudreault with methyl, as taught by Boudreault.
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 hydrogen with methyl at the position corresponding to RC of Formula II 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 Boudreault as modified by Kim and Zhang (2) which has identical structure as the Compound of Boudreault as modified by Kim and Zhang except the hydrogen at the position pointed by the arrow in the figure above is a methyl group.
Claims 1-2, 6-8, 11-13, 17, and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Ji et al. (US 2018/0138427 A1, hereafter Ji).
Regarding claims 1-2, 6-8, 11-13, 17, and 19-20, Ji discloses a compound comprising a first ligand LA of Formula I and used for an organic light emitting device ([0016]-[0031]) and exemplifies Compound Ir(LB183)2LA21 ([0135]).
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In the Compound Ir(LB183)2LA21 of Ji, the right ligand corresponding to the LA of Formula I does not comprises a CD3 group; however, Ji does teach that a ligand comprising a CD3 groups (see ligand LA41 in [0082]).
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 Ir(LB183)2LA21 of Ji by substituting the first ligand with LA41, 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 exemplifies ligands of LA of Formula I 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).
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The modification provides Modified compound of Ji, meeting all the limitations of claims 1-2, 6-8, 11-13, and 19.
Ji does not disclose a specific organic light emitting device comprising the Modified compound of Ji; however, Ji does teach that the compound of Ji can be used for the organic layer of an organic light emitting device having structure of an anode, an organic layer, and a cathode ([0030]).
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 Modified compound of Ji by incorporating it in an organic light emitting device, 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 modification provides Modified organic light emitting device of Ji comprising an anode, an organic layer (Modified compound of Ji), and a cathode, meeting all the limitations of claim 17.
Ji does not disclose a specific consumer product comprising the Modified organic light emitting device of Ji; however, Ji does teach that the organic light emitting device can be incorporated into a consumer product ([0030]).
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 Modified organic light emitting device of Ji 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 organic light emitting devices in a consumer product 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 comprising the Modified organic light emitting device of Ji, meeting all the limitations of claim 20.
Double Patenting
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 §§ 706.02(l)(1) - 706.02(l)(3) 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 USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The 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/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1-4, 6-9, 11-14, 17-18, and 20 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 15, 18, and 20 of US Patent no. 12,543,492 (previously Application 17/404,311, hereafter Patent ‘492). Although the claims at issue are not identical, they are not patentably distinct from each other because the claims are directed at the same aspects of the same invention.
Regarding claims 1-4, 6-9, 11-13, 17, and 20, Application ‘311 discloses a compound of Formula I (claim 1) and exemplifies a compound as shown below (claim 15) (hereafter Compound A).
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The left ligand of the Compound A has identical structure as the Formula I of the instant claims, meeting all the limitations of claims 1-4, 6-9, and 11-13.
Application ‘311 does not disclose a specific organic light emitting device comprising the Compound A; however, Application ‘311 does teach an organic light emitting device comprising an anode, an organic layer comprising the compound of Formula I, and a cathode, wherein the organic layer further comprises a host, dicarbazolyl dibenzothiophene (claim 18). The dicarbazolyl dibenzothiophene compound has identical structure as the first compound of the instant claim 19.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified Compound A by incorporating it into the organic layer with dicarbazolyl dibenzothiophene host in the organic layer of an organic light emitting device comprising an anode, an organic layer, and a cathode, as taught by Application ‘311.
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 compounds 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 Modified organic light emitting device of Patent ‘443 comprising an anode, an organic layer (dicarbazolyl dibenzothiophene as a host, Compound A), and a cathode, meeting all the limitations of claim 17.
Application ‘311 does not disclose a specific consumer product comprising the Modified organic light emitting device of Application ‘311; however, Application ‘311 does teach a consumer product comprising the organic light emitting device of Application ‘311 (claim 20).
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 Modified Organic light emitting device of Application ‘311 by incorporating it into a consumer product, as taught by Application ‘311.
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 organic light emitting devices in a consumer product 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 comprising the Modified organic light emitting device of Application ‘311, meeting all the limitations of claim 20.
Claims 1-4, 6-9, 11-13, 17, and 20-23 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 16, 19, and 20 of copending Application No. 17/745,939 (reference application, hereafter Application ‘939). Although the claims at issue are not identical, they are not patentably distinct from each other because the claims are directed at the same aspects of the same invention. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Regarding claims 1-4, 6-9, 11-13, 17, and 20-23, Application ‘939 discloses a compound of Formula I (claim 1) and exemplifies compounds (the second compound on page 319, hereafter Compound p319-2, the first compound on page 324, hereafter Compound p324-1) (claim 16).
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The left ligand of the Compound p319-2 has identical structure as the Formula I of the instant claims, meeting all the limitations of claims 1-4, 6-9, 11-13, and 21-23.
Application ‘939 does not disclose a specific organic light emitting device comprising the Compound p319-2 or p324-1; however, Application ‘939 does teach an organic light emitting device comprising an anode, an organic layer comprising the compound of Formula I, and a cathode, wherein the organic layer further comprises a host, dicarbazolyl dibenzothiophene (claim 19). The dicarbazolyl dibenzothiophene compound has identical structure as the first compound of the instant claim 19.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified Compound p319-2 (or p324-1) by incorporating it into the organic layer with dicarbazolyl dibenzothiophene host in the organic layer of an organic light emitting device comprising an anode, an organic layer, and a cathode, as taught by Application ‘939.
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 compounds 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 Modified organic light emitting device of Patent ‘443 comprising an anode, an organic layer (dicarbazolyl dibenzothiophene as a host, Compound p319-2 (or p324-1)), and a cathode, meeting all the limitations of claim 17.
Application ‘939 does not disclose a specific consumer product comprising the Modified organic light emitting device of Application ‘939; however, Application ‘939 does teach a consumer product comprising the organic light emitting device of Application ‘939 (claim 17).
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 Modified Organic light emitting device of Application ‘939 by incorporating it into a consumer product, as taught by Application ‘939.
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 organic light emitting devices in a consumer product 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 comprising the Modified organic light emitting device of Application ‘939, meeting all the limitations of claim 20.
Claims 1-4, 6-9, 11-13, 17, and 19-23 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 15, 19, and 20 of copending Application No. 17/669,864 (reference application, hereafter Application ‘864). Although the claims at issue are not identical, they are not patentably distinct from each other because the claims are directed at the same aspects of the same invention. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Regarding claims 1-4, 6-9, 11-13, 17, and 19-23, Application ‘864 discloses a compound of Formula I (claim 1) and exemplifies compounds (the second compound on page 263, hereafter Compound p263-2, the first compound on page 265, hereafter Compound p265-1) (claim 15).
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The left ligand of the Compound p263-2 has identical structure as the Formula I of the instant claims, meeting all the limitations of claims 1-4, 6-9, 11-13, and 21-23.
The left ligand of the Compound p265-1 has identical structure as the Formula I of the instant claims, meeting all the limitations of claims 1-4, 6-7, 9, 11-13, and 19.
Application ‘864 does not disclose a specific organic light emitting device comprising the Compound p263-2 or p265-1; however, Application ‘864 does teach an organic light emitting device comprising an anode, an organic layer comprising the compound of Formula I, and a cathode, wherein the organic layer further comprises a host, dicarbazolyl dibenzothiophene (claim 19). The dicarbazolyl dibenzothiophene compound has identical structure as the first compound of the instant claim 19.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified Compound p263-2 (or p265-1) by incorporating it into the organic layer with dicarbazolyl dibenzothiophene host in the organic layer of an organic light emitting device comprising an anode, an organic layer, and a cathode, as taught by Application ‘864.
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 compounds 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 Modified organic light emitting device of Patent ‘443 comprising an anode, an organic layer (dicarbazolyl dibenzothiophene as a host, Compound p263-2 (or p265-1)), and a cathode, meeting all the limitations of claims 17-19.
Application ‘864 does not disclose a specific consumer product comprising the Modified organic light emitting device of Application ‘864; however, Application ‘864 does teach a consumer product comprising the organic light emitting device of Application ‘864 (claim 17).
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 Modified Organic light emitting device of Application ‘864 by incorporating it into a consumer product, as taught by Application ‘864.
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 organic light emitting devices in a consumer product 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 comprising the Modified organic light emitting device of Application ‘864, meeting all the limitations of claim 20.
Conclusion
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/SEOKMIN JEON/Primary Examiner, Art Unit 1786
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