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 .
Election/Restrictions
Applicant's election without traverse of species (A1) a compound of Formula I, wherein M is Ir; and (B4) X is O, S, or Se in the reply filed on 2/25/2021 is acknowledged.
Upon further consideration, the species election (B1) through (B4) are merged to a single species (B1’). It is noted that the requirement of species election for (A1)-(A2) is maintained.
Applicant's election is now equated with (A1) a compound of Formula I, wherein M is Ir; and (B1’) X is BR’, CR’R”, SiR’R”, GeR’R”, SnR’R”, NR’, PR’, SbR’, BiR’, O, S, or Se.
Claim 16 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group.
Terminal Disclaimer
The terminal disclaimer filed on 05/06/2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of Application 17/518,718 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Response to Amendment
The amendment of 05/06/2026 has been entered.
Disposition of claims:
Claims 3, 7, 9, 15, 18-19, 21, and 23-24 have been canceled.
Claims 25-28 have been added.
Claims 1-2, 4-6, 8, 10-14, 16-17, 20, 22, and 25-28 are pending.
Claim 16 has been withdrawn.
Claims 1, 10, 17, and 20 have been amended.
The cancellation of claims 9, 15, 21, and 23-24 obviates the rejections of claims 9, 15, 21, and 23-24 set forth in the last Office Action.
The approved Terminal Disclaimer of 05/06/2026 obviates the provisional rejections of claims 1-2, 4-5, 8-14, 17, and 20-23 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 16, 17, and 20 of US Patent application no. 17/518,718 (reference application, hereafter Application ‘718).
The amendments of claims 1, 10, 17, and 20 have overcome the rejections of claims 1-2, 4-5, 8-9, 11-13, 17, and 20-23 under 35 U.S.C. 103 as being unpatentable over Adamovich et al. (US 2019/0280213 A1, hereafter Adamovich) in view of Ji et al. (US 2018/0138427 A1, hereafter ji) set forth in the last Office Action. The rejections have been withdrawn.
Response to Arguments
Applicant’s arguments see page 93-95 of the reply filed 05/06/2026 regarding the rejections of claims 1-2, 4-5, 8-9, 11-13, 17, and 20-23 under 35 U.S.C. 103 as being unpatentable over Adamovich in view of Ji set forth in the Office Action of 02/11/2026 have been considered.
Applicant argues that the rejections need to be withdrawn in view of the amendment.
The rejections have been withdrawn, rendering this argument moot.
Applicant’s arguments see page 95-98 of the reply filed 05/06/2026 regarding the rejections of claims 1-2, 4-5, 8-14, 17, 20-21, and 24 under 35 U.S.C. 103 as being unpatentable over Rayabarapu in view of Ji set forth in the Office Action of 02/11/2026 have been considered.
Applicant argues that the rejections need to be withdrawn in view of the amendment.
The rejections refer to the Compound of Rayabarapu as modified by Ji (see sections 76 and 85 of the last Office Action).
The compound does not read on the limitation of Formulas I and II of the amended claims. Thus, the rejections have been withdrawn.
Applicant’s arguments see page 98-100 of the reply filed 05/06/2026 regarding the rejections of claims 1-2, 4-6, 8, 11-13, and 15 under 35 U.S.C. 103 as being unpatentable over Rayabarapu et al. (US 2012/0061654 A1, hereafter Rayabarapu) in view of Ji et al. (US 2018/0138427 A1) and Boudreault et al. (US 2015/0001472 A1, hereafter Boudreault ‘472) set forth in the Office Action of 02/11/2026 have been considered.
Applicant argues that a person of ordinary skill in the art would have found no teaching or suggestion in combining the fused heterocyclic moiety of Ji having rings C, D, and E with the carbocyclic structure of Rayabarapu, and Boudreault fails to remedy the deficiencies; thus, the instant claims are nonobvious and allowable over Rayabarapu, Ji, and Boudreault.
Respectfully, the Examiner does not agree.
While an ordinary skill in the art would acknowledge that there is a difference in the ring structures between Ji and Rayabarapu (i.e. heterocyclic ring of Ji vs. carbocyclic ring of Rayabarapu), the ordinary artisan would be motivated to modify the carbocyclic ring structure of Rayabarapu in view of Ji to achieve the benefits taught by Ji (i.e. advantage of the extended benzene ring), because the ordinary artisan would expect the benefits of the fused benzene ring taught by Ji exists regardless the compound Rayabarapu has a carbocyclic backbone structure or a heterocyclic backbone structure.
Rayabarapu discloses a compound (Formula I) used for an organic light emitting device ([0015]) and exemplifies Compound 122 ([0065]).
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In the compound of Formula I of Rayabarapu, RA is a substituent having the structure
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, wherein X can be CRR’; and R1 can be alkenyl ([0016]).
The Compound 86 of Rayabarapu has substituents hydrogen at the positions corresponding to R1 of Formula I of Rayabarapu, which does not read on the limitation of the instant claims; however, Rayabarapu does teach R1 can be alkenyl ([0016]).
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While Rayabarapu is silent about connection of the adjacent substituents at the positions R1 of the Formula I of Rayabarapu, an ordinary skill in the art would understand two adjacent alkenyl groups can be connected to form a fused benzene ring because a fused benzene is considered as two substituted alkenyl groups, and the alkenyl group at the position R1 of the compound of Raybarapu can be any alkenyl group including a substituted and/or connected alkenyl.
Ji discloses a compound comprising a bidentate ligand LA and used for an organic light emitting device (Formula I in [0016]-[0031]). Raybarapu and Ji are in the same art area (i.e. Ir complex used as the emitter of an organic light emitting device).
The bidentate ligand LA has a heterocyclic ring (i.e. pyridine) coordinating to the metal center, wherein the heterocyclic ring necessarily has a 5-6-6 fused rings of C, D, and E ([0016], [0020]). Ji exemplifies a formula ([0077], the 1st formula on page 6, hereafter Formula p6-1).
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Ji teaches that the fused rings provides strong interaction with host in an OLED device, enhanced electronic conductivity, larger dipole moment, and better light extraction, which help improvement of efficiency and performance in an OLED device ([0137]).
The compounds of Ji has a heteroatom selected from O, S, Se, or NR at the position X of the Formula p6-1 of Ji which is different from the compound of Rayabarapu wherein the heteroatom at the equivalent position is C; however, an ordinary skill in the art would understand similar benefits should be achievable in the compound of Rayabarapu, because the benefits taught by Ji essentially stems from extension of conjugated aromatic rings B-C-D-E, indicating more conjugated rings B-C-D-E should be more beneficial as compared to less conjugated rings B-C-D in terms of the electronic conductivity, dipole moment, and light extraction.
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound 122 of Rayabarapu by incorporating a fused benzene ring to the terminal benzene ring including R1 of the
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of Rayabarapu (i.e. substituting the hydrogen atoms at the positions corresponding to R1 with a fused benzene ring), as taught by Rayabarapu and Ji.
For at least this reason, the argument is not found persuasive. The rejections are maintained.
Applicant’s arguments see page 96-98 of the reply filed 05/06/2026 regarding the rejections of Claims 1-2, 4-5, 8-14, 17, and 23 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 11, and 17-18 of US Patent no. 11,081,658 (hereafter Patent ‘658) set forth in the Office Action of 02/11/2026 have been considered.
Applicant argues that the conflicting claims fail to teach or suggest the limitation of the amended claims; thus, the instant claims are patentably distinct from those of US Patent No. 11,081,658.
The rejections refer to an embodiment of claim 17 (col. 405, the 4th compound, hereafter Example 1; see the structure in the section 113 of the last Office Action).
The Example 1 compound does not read on the limitation of the Formulas I and II of the amended claims; thus, the rejections are withdrawn.
However, the Patent ‘658 is still applicable to make new grounds of rejection to the amended claims. Patent ‘658 discloses a compound comprising a ligand LA represented by Formula I (claim 1). Patent ‘658 exemplifies a compound (col. 405, the 4th compound, hereafter Example 1).
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In the Example 1, the isobutyl group (i.e. the part enclosed in the dashed circle in the figure above) is not an electron withdrawing group; however, Patent ‘658 does teach the left ligand can be represented by
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, wherein RC can be a combination of alky and halogen (claim 11). Patent ‘658 exemplifies a ligand having structure of
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, wherein RE is R8
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; and RB is R1
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; and G is G5
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(ligand 37 in claim 12).
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Example 1 compound by substituting the isobutyl group with 2-methyl 2-trifluoromethyl propyl group
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, as taught by Patent ‘658.
The modification provides Modified compound of Patent ‘658.
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New grounds of rejection are applied. The amendment necessitates new grounds of rejection, making this Office Action final.
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 1-2, 4-6, 8, 11-13, 17, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Rayabarapu et al. (US 2012/0061654 A1, hereafter Rayabarapu) in view of Ji et al. (US 2018/0138427 A1) and Boudreault et al. (US 2015/0001472 A1, hereafter Boudreault ‘472).
Regarding claims 1-2, 4-6, 8, 11-13, 17, and 20, Rayabarapu discloses a compound (Formula I) used for an organic light emitting device ([0015]) and exemplifies Compound 122 ([0065]).
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In the Formula I of Rayabarapu, RA is a substituent having the structure
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, wherein X can be CRR’; and R1 can be alkenyl ([0016]).
Rayabarapu does not disclose a specific organic light emitting device comprising the Compound 122 of Rayabarapu; however, Rayabarapu does teach that the compound of Rayabarapu can be used as a dopant with a host in the emissive layer of an organic light emitting device having structure of an anode, an emissive layer, and a cathode ([0029], example in [0110]).
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 122 of Rayabarapu by incorporating it into the emissive layer of an organic light emitting device, as taught by Rayabarapu.
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 dopants of Rayabarapu in the device of Rayabarapu 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 Rayabarapu comprising an anode, an emissive layer (a host, Compound 122 as a dopant), and a cathode.
Rayabarapu does not disclose a consumer product comprising the Modified organic light emitting device Rayabarapu; however, Rayabarapu does teach that the organic light emitting device of Rayabarapu can be incorporated in a consumer product such as a flat panel display ([0030], [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 Modified organic light emitting device of Rayabarapu by incorporating it into a consumer product, as taught by Rayabarapu.
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 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 consumer product of Rayabarapu comprising the Modified organic light emitting device of Rayabarapu.
The Compound 122 of Rayabarapu has substituents hydrogen at the positions corresponding to R1 of Formula I of Rayabarapu, which does not read on the limitation of the instant claims; however, Rayabarapu does teach R1 can be alkenyl ([0016]).
While Rayabarapu is silent about connection of the adjacent substituents at the positions R1 of the Formula I of Rayabarapu, an ordinary skill in the art would understand two adjacent alkenyl groups can be connected to form a fused benzene ring because a fused benzene can be considered as two substituted alkenyl groups.
Ji discloses a compound comprising a bidentate ligand LA and used for an organic light emitting device (Formula I in [0016]-[0031]). The bidentate ligand LA has a heterocyclic ring (i.e. pyridine) coordinating to the metal center, wherein the heterocyclic ring necessarily has a 5-6-6 fused rings of C, D, and E ([0016], [0020]). Ji exemplifies a formula ([0077], the 1st formula on page 6, hereafter Formula p6-1).
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Ji teaches that the fused rings provides strong interaction with host in an OLED device, enhanced electronic conductivity, larger dipole moment, and better light extraction, which help improvement of efficiency and performance in an OLED device ([0137]).
The compounds of Ji has a heteroatom selected from O, S, Se, or NR at the position X of the Formula p6-1 of Ji which is different from the compound of Rayabarapu wherein the heteroatom at the equivalent position is C; however, an ordinary skill in the art would understand similar benefits should be achievable in the compound of Rayabarapu, because the benefits taught by Ji essentially stems from extension of conjugated aromatic rings B-C-D-E, indicating more conjugated rings B-C-D-E should be more beneficial as compared to less conjugated rings B-C-D in terms of the electronic conductivity, dipole moment, and light extraction.
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 122 of Rayabarapu by incorporating a fused benzene ring to the terminal benzene ring including R1 of the
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of Rayabarapu (i.e. substituting the hydrogen atoms at the positions corresponding to R1 with a fused benzene ring), as taught by Rayabarapu and Ji.
The motivation of doing so would have been to provides strong interaction with host in an OLED device, enhanced electronic conductivity, larger dipole moment, and better light extraction, which help improvement of efficiency and performance in an OLED device based on the teaching of Ji.
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).
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The modification provides Compound of Rayabarapu as modified by Ji (3), which has identical structure as Applicant’s compound of Formulas I and II, meeting all the limitations of claims 1-2, 4-6, 8, and 11-13.
The modification also provides Organic light emitting device of Rayabarapu as modified by Ji comprising an anode, an emissive layer (a host, Compound of Rayabarapu as modified by Ji (3) as a dopant), and a cathode, meeting all the limitations of claim 17.
The modification also provides Consumer product of Rayabarapu as modified by Ji comprising the Organic light emitting device of Rayabarapu as modified by Ji, meeting all the limitations of claim 20.
Claim 28 is rejected under 35 U.S.C. 103 as being unpatentable over Rayabarapu et al. (US 2012/0061654 A1, hereafter Rayabarapu) in view of Ji et al. (US 2018/0138427 A1) as applied to claims 1-2, 4-6, 8, 11-13, 17, 20 above, further in view of Boudreault et al. (US 2015/0001472 A1, hereafter Boudreault ‘472).
Regarding claim 28, the compound of Rayabarapu as modified by Ji (3) reads on all the features of the compound of Applicant’s Formulas I and II as outlined above.
The compound has similar structure as Applicant’s embodiment of claim 28 (the last compound on page 90). The only difference is that the terminal methyl groups of the acetylacetone ligand of the compound are required to be a pentyl group. However, Rayabarapu teaches formula
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, wherein R4 and R5 can be alkyl ([0025]-[0026]).
Boudreault ‘472 discloses an Ir complex comprising an acetylacetonate ligand of Formula I and used for an organic light emitting device ([0015], [0002]) and exemplifies ligand LA1 ([0041]).
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Boudreault ‘472 teaches that the device comprising an Ir complex containing the ligand LA1 provides smaller FWHM, lower voltage and higher luminous, external quantum, and power efficiencies than the comparative device comprising an acetylacetonate ligand (Compare Example 1 comprising Compound 8 with the Comparative Example 1 comprising Comparative Compound 1 in [0073]-[0076] and Table 3).
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 Rayabarapu as modified by Ji (3) by substituting the methyl group at the positions corresponding to R4 and R5 of Formula
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of Rayabarapu, as taught by Rayabarapu and Boudreault ‘472.
The motivation of doing so would have been to provides smaller FWHM, lower voltage and higher luminous, external quantum, and power efficiencies 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). The substitution 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 Rayabarapu as modified by Ji and Boudreault ‘472, which has identical structure as the specific embodiment of claim 28 (the last compound on page 90).
Claims 1-2, 4-5, 8, 11-13, 17, 20, 25, and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2019/0237683 A1, hereafter Boudreault ‘683) in view of Ji et al. (US 2018/0138427 A1, hereafter Ji).
Regarding claims 1-2, 4-5, 8, 11-13, 17, 20, 25, and 27, Boudreault ‘683 discloses a compound comprising a ligand LA of Formula I ([0015]) and used for an organic light emitting device ([0025]). Boudreault ‘683 exemplifies an organic light emitting device comprising an anode, an emissive layer (Compound Ir(LAI-139)2(LB22) as a dopant, Compound H as a host), and a cathode (Example 1 in [0253]).
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In the Compound Ir(LAI-139)2(LB22), the left ligand corresponding to the ligand LA of Formula I is not thiophene containing ligand; however, Boudreault ‘683 does teach that the ligand LA can be a thiophene-containing ligand ([0092], the 10th structure, hereafter Formula A) and exemplifies a ligand XLVIII-LA1687, having structure of
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, wherein R1 = RB1
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, R11 = H, R12 =RC4
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, and R2 = RB1
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([0101]-[0102]).
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(LAI-139)2(LB22) by substituting the left ligand at the position corresponding to LA with a ligand XLVII-LA1687, as taught by Boudreault ‘683.
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 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 compound of Boudreault ‘683.
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In the Modified compound of Boudreault ‘683, the substituents at the positions corresponding to R16 to R18 of Formula A are each hydrogen, which does not read on the limitation of Formula I of the instant claims; however, Boudreault ‘683 does teach that R16 to R18 can be alkenyl, wherein any two substituents can be joined to form into a ring ([0092]).
Ji discloses a compound used for an organic light emitting device (Formula I in [0016]-[0031]). The compound of Ji contains two fused rings D and E to the five membered heterocyclic ring containing X which is fused to the pyridine ring B of the ligand. Ji exemplifies ligands LA1 and LA21 ([0082]).
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Ji teaches that the compound of Ji provides strong interaction with the host, enhanced electronic conductivity of the emission layer, large dipole moment, and improved efficiency of the OLED device ([0137]).
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 Boudreault ‘683 by substituting the hydrogen at atoms at any two adjacent positions corresponding to R16 to R18 of Formula A of Boudreault ‘683 with a fused benzene ring, as taught by Boudreault ‘683 and Ji.
The motivation of doing so would have been to provide strong interaction with the host, enhanced electronic conductivity of the emission layer, large dipole moment, and improved efficiency of the OLED device, based on the teaching of Boudreault ‘683.
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).
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The modification provides Compound of Boudreault ‘683 as modified by Ji, meeting all the limitations of claims 1-2, 4-5, 8, 11-13, 25, and 27. It is noted that the position of the fused benzene ring can be 1-2 as shown above, or 2-3. The position 1-2 in the figure was selected for better exhibition purpose.
The modification also provides Organic light emitting device of Boudreault ‘683 as modified by Ji comprising an anode, an emissive layer (Compound of Boudreault ‘683 as modified by Ji as a dopant, Compound H as a host), and a cathode, meeting all the limitations of claim 17.
Boudreault ‘683 does not disclose a specific consumer product comprising the Organic light emitting device of Boudreault ‘683 as modified by Ji; however, Boudreault ‘683 does teach a consumer product comprising the organic light emitting device of Boudreault ‘683 ([0030], [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 Boudreault ‘683 as modified by Ji by incorporating it into a consumer product, as taught by Boudreault ‘683 and 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). 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 ‘683 as modified by Ji, meeting all the limitations of claims 20.
Claims 1-2, 4-5, 8, 10-14, 22, and 26 are rejected under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2019/0237683 A1, hereafter Boudreault ‘683) in view of Ji et al. (US 2018/0138427 A1, hereafter ji) and Chen et al. (“A simple and efficient approach toward deep-red to near-infrared-emitting iridium(III) complexes for organic light-emitting diodes with external quantum efficiencies of over 10%”, Chem. Sci. 2020, vol. 11, page 2342-2349, hereafter Chen).
Regarding claims 1-2, 4-5, 8, 10-14, 22, and 26, Boudreault ‘683 discloses a compound comprising a ligand LA of Formula I ([0015]) and used for an organic light emitting device ([0025]). Boudreault ‘683 discloses more specific structural formula of the ligand LA ([0092], the 10th structure, hereafter Formula A). Boudreault ‘683 exemplifies Compound XLVII-11342 represented by Ir(XLVII-LA1585)2(LB1) ([0109]-[0110]; ligand XLVII-LA1585 in [0101]-[0102]; and ligand LB1 in [0107]-[0108]).
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The substituents of the Compound XLVII-11342 at the position corresponding to R16 to R19 of Formula A are each hydrogen, which does not read on the limitation of Formula I of the instant claims; however, Boudreault ‘683 does teach that R16 to R19 can be alkenyl, wherein any two substituents can be joined to form into a ring ([0092]).
Ji discloses a compound used for an organic light emitting device (Formula I in [0016]-[0031]). The compound of Ji contains two fused rings D and E to the five membered heterocyclic ring containing X which is fused to the pyridine ring B of the ligand. Ji exemplifies ligands LA1 ([0082]).
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Ji teaches that the compound of Ji provides strong interaction with the host, enhanced electronic conductivity of the emission layer, large dipole moment, and improved efficiency of the OLED device ([0137]).
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 XLVII-11342 of Boudreault ‘683 by substituting the hydrogen at atoms at any two adjacent positions corresponding to R16 and R17 of Formula A of Boudreault ‘683 with a fused benzene ring, as taught by Boudreault ‘683 and Ji.
The motivation of doing so would have been to provide strong interaction with the host, enhanced electronic conductivity of the emission layer, large dipole moment, and improved efficiency of the OLED device, based on the teaching of Boudreault ‘683.
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).
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The modification provides Compound of Boudreault ‘683 as modified by Ji.
The compound does not have a nitrile group at the position corresponding to the R at X2 of Formula I of Boudreault ‘683; however, Boudreault ‘683 does teach the R at X2 of Formula I can be a nitrile group ([0081]).
Chen discloses an Ir complex comprising a phenyl-pyridine-based ligand (CNIr in Scheme 2) used for an organic light emitting device (Abstract, Fig. 3).
Chen teaches a CN group provides decreased LUMO, narrow emission energy gap, and long wavelength emission (page 2343, column 2, last paragraph).
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 Boudreault ‘683 as modified by Ji by substituting the hydrogen at the position corresponding to R at X2 of Formula I of Boudreault ‘683 with a nitrile group, as taught by Boudreault ‘683 and Chen.
The motivation of doing so would have been to provide decreased LUMO, narrow emission energy gap, and long wavelength emission, based on the teaching of Chen.
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).
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The modification provides Compound of Boudreault ‘683 as modified by Ji and Chen, meeting all the limitations of claims 1-2, 4-5, 8, 10-14, 22, and 26.
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 1-2, 4-5, 8, 10-14, 17, 22, and 25-27 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 11, and 17-18 of US Patent no. 11,081,658 (hereafter Patent ‘658). 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 1-2, 4-5, 8, 10-14, 17, 22, and 26, Patent ‘658 discloses a compound comprising a ligand LA represented by Formula I (claim 1). Patent ‘658 exemplifies a compound (col. 405, the 4th compound, hereafter Example 1).
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In the Example 1, the isobutyl group (i.e. the part enclosed in the dashed circle in the figure above) is not an electron withdrawing group; however, Patent ‘658 does teach the left ligand can be represented by
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, wherein RC can be a combination of alky and halogen (claim 11). Patent ‘658 exemplifies a ligand having structure of
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, wherein RE is R8
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; and RB is R1
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; and G is G5
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(ligand 37 in claim 12).
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 Example 1 compound by substituting the isobutyl group with 2-methyl 2-trifluoromethyl propyl group
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, as taught by Patent ‘658.
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 exemplified ligands LA in the compound of Patent ‘658 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 Patent ‘658, meeting all the limitations of claims 1-2, 4-5, 8, 10-14, 22, and 26.
Patent ‘658 does not disclose a specific organic light emitting device comprising the Modified compound of Patent ‘658; however, Patent ‘658 does teach an organic light emitting device comprising an anode, an organic layer, and a cathode, wherein the organic layer comprises a compound of Patent ‘658 (claim 18).
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 Patent ‘658 by incorporating it into the organic layer of an organic light emitting device, as taught by Patent ‘658.
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 organic layer materials of the Patent ‘658 in the OLED device of Patent ‘658 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 ‘658 comprising an anode, an organic layer containing the Modified compound of Patent ‘658, and a cathode, meeting all the limitations of claim 17.
Regarding claims 25 and 27, the Modified compound of Patent ‘658 reads on all the features of claim 1 as outlined above.
The fluoroalkyl group is not in the list of the claimed substituents; however, Patent ‘658 does teach the left ligand can be represented by
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, wherein RC can be aryl (claim 11). Patent ‘658 exemplifies R26 as the aryl group (claim 12, i=55 in column 325).
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 Example 1 compound by substituting the 2-methyl 2-trifluoromethyl propyl group with R26
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, as taught by Patent ‘658.
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 exemplified substituents in the compound of Patent ‘658 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 compound of Patent ‘658 (2) which has identical structure as Modified compound of Patent ‘658 except the 2-methyl 2-trifluoromethyl propyl group is replaced by R26
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.
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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/SEOKMIN JEON/Primary Examiner, Art Unit 1786
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