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 (A2) (a compound comprising a ligand LA of Formula 1 coordinate to a metal M wherein the ring A is a 6-membered ring; wherein Z1 is N; X1 through X7 are CR1; and M is Os) in the reply filed on 08/13/2024 is acknowledged.
In the Office Action of 09/05/2024, the requirement of species election was updated. Applicant’s election of 08/13/2024 is equated with the updated Species (A2’) (a compound comprising a ligand LA of Formula 1 coordinate to a metal M wherein the ring A is a 6-membered ring; wherein Z1 is N or C; X1 through X7 are CR1).
The structural formula claimed in claims 35-38 are directed to a 5-membered ring at the position corresponding to the ring A of Applicant’s Formula 1. Applicant’s election is directed to a 6-membered ring; thus, claims 35-38 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group.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 12/23/2025 has been entered.
Disposition of claims:
Claims 2-3, 5-6, 8, 11, 16-17, 19, and 21-28 have been canceled.
Claims 32-38 have been added.
Claims 1, 4, 7, 9-10, 13-15, 18, 20, and 29-38 are pending.
Claims 35-38 are withdrawn.
Claims 1, 10, 13, and 18 have been amended.
Response to Arguments
Applicant’s arguments see page 63-73 of the reply filed 12/23/2025 regarding the rejections of claims 1, 4, 7, 9-10, 13-15, 18, 20, 29, 31, and 33-34 under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Noboru et al. (WO 2006/100925, a machine translated English document is referred to, hereafter Noboru), the rejections of claims 1, 4, 7, 9-10, 13-15, 18, 20, 29, 31, and 33-34 under 35 U.S.C. 103 as being unpatentable over Thompson et al. (WO 2005/113704 A2, hereafter Thompson) in view of Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective”, ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo) and Noboru et al. (WO 2006/100925, a machine translated English document is referred to, hereafter Noboru), and the rejections of claims 1, 4, 7, 9, 13-15, 18, 20, and 31-32 under 35 U.S.C. 103 as being unpatentable over Thompson et al. (WO 2005/113704 A2) set forth in the Office Action of 08/27/2025 and Declaration under 37 C.F.R. 1.132 filed on 12/23/2025 (hereafter the Declaration) have been considered.
Applicant argues that the inventive complex exhibit much more desirable emission spectra in the red range of the spectrum compared to the infrared emission of the comparative complex, and a desirably large emission gap and improved quantum yield (the last paragraph of page 67, the first and last paragraphs of page 69).
No experimental data including emission spectra and quantum yield were provided to support the argument. Applicant exhibits the T1 values obtained from DFT calculations and compared the T1 values of the inventive compounds with that of comparative compounds. However, Applicant fails to show how well the calculated T1 value reproduces the emission spectra and quantum yields of the real-world materials. It is unclear whether the inventive compounds actually possess practically and significantly improved material properties as compared to the comparative compound in a real-world product or device. It is Applicant’s burden to establish the unexpected result is practically significant (MPEP 716.02(b)).
The evidence relied upon should establish "that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance." Ex parte Gelles, 22 USPQ2d 1318, 1319 (Bd. Pat. App. & Inter. 1992) (Mere conclusions in appellants’ brief that the claimed polymer had an unexpectedly increased impact strength "are not entitled to the weight of conclusions accompanying the evidence, either in the specification or in a declaration."); Ex parte C, 27 USPQ2d 1492 (Bd. Pat. App. & Inter. 1992) (Applicant alleged unexpected results with regard to the claimed soybean plant, however there was no basis for judging the practical significance of data with regard to maturity date, flowering date, flower color, or height of the plant.). See also In re Nolan, 553 F.2d 1261, 1267, 193 USPQ 641, 645 (CCPA 1977) and In re Eli Lilly, 902 F.2d 943, 14 USPQ2d 1741 (Fed. Cir. 1990) as discussed in MPEP § 716.02(c).
Applicant recites “the relative differences between the HOMO, LUMO, S1, T1, and bond dissociation energy values calculated with B3LYP protocol are expected to reproduce experimentally quite well” (item 6 in the Declaration) and cited the reference by Hong. Hong did not use the same computational method that Applicant used (i.e. compare the methods in Table S1 of Supporting Information of Hong with the method described in item 4 of the Declaration). Additionally the material system that Hong studied is different from the claimed compound. On top of that, the Examiner points out the calculated value swings significantly depending on which functional and basis set are used; thus, it cannot be determined the calculated values are practically significant. For instance, Hong compares the VT1 values obtained by various computational methods (see Table S1 of Supporting Information of Hong). In the B3LYP/6-31G(d) method, the HOMO-LUMO gap (H-L gap) for the 2-Cz-DBT molecule is 4.11 eV while in the w-B97XD/6-31G(d) method, the HOMO-LUMO gap for the same molecule is 7.70 eV which is 87% larger than the value obtained by the different method of B3LYP/6-31G(d). Such difference exists even in the relative differences. In the B3LYP/6-31G(d) method, the difference of VS1-VT1 for the 2-Cz-DBT molecule is 0.47 eV which is 30.5% larger than that for the 2-Cz-2CN-DBT molecule (0.36 eV). On the other hand, when w-B97XD/6-31G(d) was used for the same material system, the VS1-VT1 values for the 2-Cz-DBT molecule (1.05 eV) is only 5% larger than that for the 2-Cz-2CN-DBT molecule (1.00 eV). That is, even when the relative difference is compared, the degree of the relative difference varies a lot (30.5% vs. 5 %) depending on which method and material system are used.
For at lest this reason, the arguments are not persuasive.
The amended claims deleted a proviso (i.e. provided that at least one of X5, X6, and X7 is CR2 wherein R2 is alkyl or cycloalkyl). The rejections have been updated due to the amendment. The amendment necessitates new grounds of rejections, making this Office Action final.
Applicant’s arguments see page 63-73 of the reply filed 12/23/2025 regarding the rejections of claims 1, 4, 7, 9-10, 13-15, 18, 20, 29, 31, and 33-34 under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Noboru et al. (WO 2006/100925, a machine translated English document is referred to, hereafter Noboru), the rejections of claims 1, 4, 7, 9-10, 13-15, 18, 20, 29, 31, and 33-34 under 35 U.S.C. 103 as being unpatentable over Thompson et al. (WO 2005/113704 A2, hereafter Thompson) in view of Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective”, ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo) and Noboru et al. (WO 2006/100925, a machine translated English document is referred to, hereafter Noboru), and the rejections of claims 1, 4, 7, 9, 13-15, 18, 20, and 31-32 under 35 U.S.C. 103 as being unpatentable over Thompson et al. (WO 2005/113704 A2) set forth in the Office Action of 08/27/2025 and Declaration under 37 C.F.R. 1.132 filed on 12/23/2025 (hereafter the Declaration) have been considered.
Applicant’s arguments see page 70-73 of the reply filed 12/23/2025 regarding the rejections of claims 1, 4, 7, 9-10, 13-14, 18, 20, 31, and 33 under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1, hereafter Djurovich) in view of Liu et al. (“Organic light-emitting devices based on a highly robust osmium(II) complex”, J. Appl. Phys. 2006, vol. 100, page 094508-1 to -4, hereafter Liu) and Thompson et al. (WO 2005/113704 A2, hereafter Thompson), the rejections of claims 13-15 and 20 under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Liu et al. (“Organic light-emitting devices based on a highly robust osmium(II) complex”, J. Appl. Phys. 2006, vol. 100, page 094508-1 to -4) and Thompson et al. (WO 2005/113704 A2) as applied to claims 1, 4, 7, 9-10, 13-14, 18, 20, 31, and 33 above, further in view of Adamovich et al. (US 2013/0112952 A1, hereafter Adamovich), the rejection of claim 29 under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Liu et al. (“Organic light-emitting devices based on a highly robust osmium(II) complex”, J. Appl. Phys. 2006, vol. 100, page 094508-1 to -4) and Thompson et al. (WO 2005/113704 A2) as applied to claims 1, 4, 7, 9-10, 13-14, 18, 20, 31, and 33 above, further in view of Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective”, ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo), the rejections of claims 1, 4, 7, 9-10, 13-14, 18, 20, 29, 31, and 33 under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Noboru et al. (WO 2006/100925, a machine translated English document is referred to, hereafter Noboru) and Wilkinson et al. (“Luminescent Complexes of Iridium(III) Containing N^C^N-Coordinating Terdentate Ligands”, Inorg. Chem. 2006, vol. 45, page 8685-8699, hereafter Wilkinson), and the rejections of claims 13-15 and 20 under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Noboru et al. (WO 2006/100925, a machine translated English document is referred to) and Wilkinson et al. (“Luminescent Complexes of Iridium(III) Containing N^C^N-Coordinating Terdentate Ligands”, Inorg. Chem. 2006, vol. 45, page 8685-8699) as applied to claims 1, 4, 7, 9-10, 13-14, 18, 20, 29, 31, and 33 above, further in view of Adamovich et al. (US 2013/0112952 A1) set forth in the Office Action of 09/05/2024 and Declaration under 37 C.F.R. 1.132 filed on 12/23/2025 have been considered.
Applicant argues that the inventive complex exhibit much more desirable emission spectra in the red range of the spectrum compared to the infrared emission of the comparative complex, and a desirably large emission gap and improved quantum yield (the last paragraph of page 70, the 4th paragraph page 71, the 3rd paragraph of page 72, and the 3rd paragraph of page 73).
As outlined above, no experimental data including emission spectra and quantum yield were provided to support the argument. It is unclear whether the inventive compounds actually possess practically and significantly improved material properties as compared to the comparative compound in a real-world product or device. For the same reasons outlined above, the arguments are not persuasive.
The amended claims deleted a proviso (i.e. provided that at least one of X5, X6, and X7 is CR2 wherein R2 is alkyl or cycloalkyl). Due the amendment the previously withdrawn rejections are re-applied. The amendment necessitates new grounds of rejections, 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, 4, 7, 9-10, 13-15, 18, 20, 29, 31, and 33-34 are rejected under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Noboru et al. (WO 2006/100925, a machine translated English document is referred to, hereafter Noboru).
Regarding claims 1, 4, 7, 9-10, 13-15, 18, 20, 29, 31, and 33, Djurovich discloses a compound having the following structure (the first structure in [0014]; hereafter Formula 014-1).
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Wherein M is a metal; R1 and R2 can be hydrogen, alkyl, or substituted or unsubstituted heteroaryl; (X-Y) can be an ancillary ligand; a is 0-4; m is 1 to maximum number of ligands that may be attached to metal M; m + n is the maximum number of ligands that may be attached to metal M ([0018]).
Djurovich exemplifies Ir as the metal M ([0064]; dopant A in [0112]), hydrogen as R1 ([0018]; phenyl pyridine ligand in [0059]), pyridine as the heteroaryl group ([0073]), and methyl as the alkyl group ([0066]).
Djurovich does not exemplifies a specific compound structure wherein M is Ir, R1 and R2 are each hydrogen; however, Djurovich does teach Ir as the metal M ([0064]; Ir as the metal center of dopant A in [0112]), hydrogen as R1 and R2 (substituents of the phenyl pyridine ligand in [0018], [0059]), and a of each pyridine and phenyl ring being 4 (number of substituents of the phenyl pyridine ligand in [0059]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified Formula 014-1 of Djurovich by selecting M to be Ir; R1 and R2 to be hydrogen; a to be 4, as taught by Djurovich.
The substitution of the structures at the positions corresponding to M, R1, R2, and a in the Formula 014-1 of Djurovich would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Each selection of exemplified structures at the positions corresponding to M, R1, R2, and a in the Formula 014-1 of Djurovich (i.e. Ir as M, H as R1, H as R2, and 4 as a) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides the Modified compound of Djurovich as shown below.
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Djurovich does not disclose a specific tridentate ligand; however, Djurovich does teach that a substituent can be added to the compound of Djurovich such that the compound can be linked to form a multidentate ligand. Djurovich further teaches that this type of linking can increase stability relative to unlinked structure ([0054]).
Djurovich teaches that the substituent, R2 of Formula 014-1 can be a heteroaryl group ([0018]) and exemplifies pyridine as the heteroaryl group ([0073]).
Noboru discloses an Ir complex comprising tridentate ligands used for the emitting layer material of an organic light emitting device ([0019]- [0028]).
Noboru teaches that a tridentate ligand has more bonds with the central metal than a bidentate ligand such as a phenyl pyridine ligand such that energy transfer between the metal and the ligand is easy, provides highly efficient light emission, and enables to obtain a larger stabilization energy associated with the formation of the complex ([0036]).
Noboru exemplifies a pyridine group substituted to the bidentate ligand of phenyl pyridine to form a tridentate ligand ([0053]; and multiple examples including Compounds 1-1, 2-2, 2-3, 2-8, 3-4, 3-7 in [0057]).
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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 Djurovich by substituting hydrogen at the substitution position 5 of the phenyl ring (see the substitution positions 1-6 in the figure of the Modified compound of Djurovich above) with a pyridine group, as taught by Djurovich and Noboru.
The motivation for doing so would have been to provide the compound with more bonds with the central metal than a bidentate ligand such that energy transfer between the metal and the ligand is easy, highly efficient light emission is provided, and a larger stabilization energy associated with the formation of the complex is enabled based on the teaching of Noboru.
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). A pyridinyl group as R2 of Formula 014-1 of Djurovich is one of exemplified substituent groups. The substitution of hydrogen with pyridine would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of the pyridinyl group at R2 would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides Compound of Djurovich as modified by Noboru.
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The Compound of Djurovich as modified by Noboru, meeting all the limitations of claims 1, 4, 7, 9-10, 31, and 33.
Djurovich in view of Noboru does not disclose a specific organic light emitting device comprising a Compound of Djurovich as modified by Noboru; however, Djurovich does teach that the compound of Djurovich can comprise the organic layer between a cathode and an anode of an organic light emitting device (Abstract, claim 6).
Djurovich further exemplifies an organic light emitting device comprising anode (ITO), an emission layer comprising mCP as a host and a compound of Djurovich (dopant A) used as an emissive dopant, and a cathode (Al) (Example 1 in [0100]- [0101]).
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 of Djurovich as modified by Noboru by substituting the emissive dopant of the emission layer of an organic light emitting device of Djurovich (Example 1) with the Compound of Djurovich as modified by Noboru, as taught by Djurovich.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, both dopant A and the Compound of Djurovich as modified by Noboru are encompassed by the compound of Djurovich represented by Formula 014-1. The substitution of the compounds of Djurovich in the device of Djurovich would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The resultant device comprises anode (ITO), an emission layer comprising mCP as a host and Compound of Djurovich as modified by Noboru as an emissive dopant, and a cathode (Al), wherein the emission layer materials are equated with a formulation, meeting all the limitations of claims 13-15 and 20.
Djurovich in view of Noboru does not disclose a specific consumer product comprising the organic light emitting device of Djurovich as modified by Noboru; however, Djurovich does teach the device in accordance with embodiment of the invention can be incorporated into a consumer product including a flat panel display ([0055]).
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 Djurovich as modified by Noboru by incorporating it into a flat panel display, as taught by Djurovich.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, substitution of organic light emitting devices of Djurovich in the flat panel display of Djurovich would have been substitution of one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides a flat panel display comprising an organic light emitting device of Djurovich as modified by Noboru, wherein the flat panel display is a consumer product, meeting all the limitations of claim 18.
Regarding claim 29, the Compound of Djurovich as modified by Noboru reads on all the features of claim 1 as outlined above.
The resultant compound does not have an alkyl substituent at the position corresponding to the R2 of Applicant’s Formula I; however, Djurovich does teach that R2 of Formula 014-1 of Djurovich can be alkyl ([0018]). Djurovich exemplifies t-butyl as the alkyl group ([0066]).
Noboru teaches that bulky substituents allows the metal to selectively tridentate with the ligand and prevent the formation of unwanted bidentate complexes ([0049]).
Noboru exemplifies a t-butyl group at the substitution position corresponding to the substituent of X6 of Applicant’s Formula I (multiple examples including Compound 1-5 in [0057]).
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 Djurovich as taught by Noboru by substituting a t-butyl group at the position corresponding to the substituent of X6 of Applicant’s Formula I, as taught by Djurovich and Noboru.
The motivation for doing so would have been to allow the metal of the compound to selectively form tridentate with the ligand and prevent the formation of unwanted bidentate complexes based on the teaching of Noboru.
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). A t-butyl group as R2 of Formula 014-1 of Djurovich is one of exemplified substituent groups. The substitution of hydrogen with t-butyl would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of the t-butyl group at R2 would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The resultant compound has following structure.
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The Compound of Djurovich as modified by Noboru, meeting all the limitations of claim 29.
Regarding claim 34, the Compound of Djurovich as modified by Noboru reads on all the features of claim 1 as outlined above.
The left ligand of the compound has similar structure as the third formula structure of the claim 34,
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. The only difference is that the pyridine group (i.e. the part enclosed by a dashed circle in the figure above) at the position corresponding to the R2 of the Formula 014-1 of Djurovich is required to be pyrazine; however, Djurovich does teach that the substituent R2 of Formula 014-1 can be a heteroaryl group ([0018]) and exemplifies pyrazine as the heteroaryl group ([0073]).
Noboru discloses a metal complex comprising tridentate ligands of Formula 1 used for the emitting layer material of an organic light emitting device ([0019]-[0028]).
Noboru teaches that a tridentate ligand has more bonds with the central metal than a bidentate ligand such as a phenyl pyridine ligand such that energy transfer between the metal and the ligand is easy, provides highly efficient light emission, and enables to obtain a larger stabilization energy associated with the formation of the complex ([0036]).
Noboru exemplifies pyrazine as the heterocyclic rings at the positions A-F of Formula (1) of Noboru ([0053]). Noboru further exemplifies pyrazine in Compound 3-8 ([0062]).
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 Djurovich as modified by Noboru by substituting the pyridine group at the position corresponding to R2 of Formula 014-1 of Djurovich with pyrazine, as taught by Djurovich and Noboru.
The motivation for doing so would have been to provide the compound with more bonds with the central metal than a bidentate ligand such that energy transfer between the metal and the ligand is easy, highly efficient light emission is provided, and a larger stabilization energy associated with the formation of the complex is enabled based on the teaching of Djurovich and Noboru.
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). A pyrazine group as R2 of Formula 014-1 of Djurovich is one of exemplified substituent groups. The substitution of hydrogen with pyrazine would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of the pyrazine group at R2 would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides Compound of Djurovich as modified by Noboru (2).
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Claims 1, 4, 7, 9-10, 13-15, 18, 20, 29, 31, and 33-34 are rejected under 35 U.S.C. 103 as being unpatentable over Thompson et al. (WO 2005/113704 A2, hereafter Thompson) in view of Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective”, ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo) and Noboru et al. (WO 2006/100925, a machine translated English document is referred to, hereafter Noboru).
Regarding claims 1, 4, 7, 9-10, 13-15, 18, 20, 29, 31, and 33, Thompson discloses a compound represented by Formula III used as the emissive material for an organic light emitting device ([0003], [0233]) and exemplifies a compound ([0252], the 4th compound on page 88, hereafter Compound p88-4; and see the pyridine ring in the figure below).
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The Compound p88-4 of Thompson has an imidazole carbene donor (i.e. the part enclosed by a dashed circle in the figure above) corresponding to Z1 and Z2 of Formula III of Thompson, which does not read on the limitation of the ring B of Applicant’s Formula I of the instant claims; however, Thompson does teach that Z1 can be N; Z2 can be C; R2 and R4 can be linked to form a 6-mebmered cyclic group ([0233]). Thompson teaches that Z2 can be a carbene donor ([0236]) and exemplifies
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as the carbene donor ([0294]). Thompson teaches the structure of the 6-membered carbene donor coordinating a metal M,
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(Table 38 on page 365).
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 p88-4 of Thompson by substituting the 5-membered imidazole carbene ring with a 6-membered pyridine carbene ring, as taught by Thompson.
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 5-membered imidazole carbene ring with 6-membered pyridine carbene ring are exemplified carbene donors. The substitution of imidazole carbene with pyridine carbene at the position corresponding to R2-Z1-Z2-R4 moiety of the Formula III of Thompson 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 Thompson, meeting all the limitations of claims 1, 4, 7, 9-10, 31, and 33
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Thompson in view of Luo and Noboru does not disclose a specific organic light emitting device comprising the Compound of Thompson as modified by Luo and Noboru; however, Thompson does teach that the compound of Formula III of Thompson is used as the emissive material ([0014], [0233]). Thompson teaches the compound of the invention can be a dopant ([0142]).
Thompson teaches the structure of an organic light emitting device comprising an anode, an emissive layer, and a cathode (Fig. 1, [0117]). Thompson teaches the emissive layer includes an emissive material and a host ([0121]). Thompson exemplifies CBP as the host ([0121]).
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 Thompson as modified by Luo and Noboru by incorporating it as a emissive dopant with a host material into the emissive layer of an organic light emitting device, as taught by Thompson.
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 emissive dopants in an organic light emitting device 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 Thompson as modified by Luo and Noboru comprising an anode, an emissive layer (the Compound of Thompson as modified by Lu and Noboru as an emissive dopant, CBP as a host), and a cathode, wherein the emissive layer material is a formulation, meeting all the limitations of claims 13-15, and 20.
Thompson in view of Luo and Noboru does not disclose a specific consumer product comprising the Organic light emitting device of Thompson as modified by Lu and Noboru; however, Thompson does teach the organic light emitting device of Thompson can be incorporated into a consumer product including flat panel displays ([0136]).
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 Thompson as modified by Luo and Noboru by incorporating it into a consumer product, flat panel displays, as taught by Thompson.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, substitution of organic light emitting devices in a consumer product would have been substitution of 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 Thompson as modified by Luo and Noboru, meeting all the limitations of claim 18.
Regarding claim 29, the Compound of Thompson as modified by Lu and Noboru reads on all the features of claim 1 as outlined above.
In the compound the phenyl group coordinating to the Os atom is unsubstituted (i.e. the ring pointed by an arrow in the figure above); however, Thompson does teach that the compound of Thompson is represented by Formula (IV),
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, wherein R8 can be alkyl ([0242]). Thompson exemplifies tert-butyl as the alkyl group ([0161]).
Luo teaches that a steric bulky group such as a tert-butyl of a transition metal complex can effectively suppress intermolecular interactions to improve the efficiency and the color purity of the organic light emitting device comprising the metal complex (page 69, column 2, paragraph 1).
Noboru discloses a complex comprising tridentate ligands used for the emitting layer material of an organic light emitting device ([0019]- [0028]). Noboru teaches the metal can be Os ([0025]).
Noboru teaches that bulky substituents allows the metal to selectively tridentate with the ligand and prevent the formation of unwanted bidentate complexes ([0049]).
Noboru exemplifies a tert-butyl group as the bulky substituent at the substitution position corresponding to the substituent of X6 of Applicant’s Formula I (see multiple examples including at least Compound 1-5 in [0057]).
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 Thompson by substituting the hydrogen atom at the position corresponding to the R8 of Formula VI of Thompson with a tert-butyl group, as taught by Thompson, Luo, and Noboru.
The motivation for doing so would have been to effectively suppress intermolecular interactions to improve the efficiency and the color purity of the organic light emitting device comprising the metal complex based on the teaching of Luo and to allow the metal of the compound to selectively form tridentate with the ligand and prevent the formation of unwanted bidentate complexes based on the teaching of Noboru.
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 a tert-butyl group at the position corresponding to R8 of Formula VI of Thompson 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 Thompson as modified by Luo and Noboru.
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The Compound of Thompson as modified by Luo and Noboru, meeting all the limitations of claim29.
Regarding claim 34, the Compound of Thompson as modified by Lu and Noboru reads on all the features of claim 1 as outlined above.
The left ligand of the compound has similar structure as the third formula structure of the claim 34,
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. The only difference is that the pyridine group (i.e. the part enclosed by a dashed circle in the figure above) at the position corresponding to the ring C of Formula (IX) of Thompson
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([0245]) is required to be pyrazine; however, Thompson does teach that the ring C in the Formula (IX) of Thompson can be 6-membered cyclic group ([0245]).
Noboru discloses a metal complex comprising tridentate ligands of Formula 1 used for the emitting layer material of an organic light emitting device ([0019]-[0028]).
Noboru teaches that a tridentate ligand has more bonds with the central metal than a bidentate ligand such as a phenyl pyridine ligand such that energy transfer between the metal and the ligand is easy, provides highly efficient light emission, and enables to obtain a larger stabilization energy associated with the formation of the complex ([0036]).
Noboru exemplifies pyrazine as the heterocyclic rings at the positions A-F of Formula (1) of Noboru ([0053]). Noboru further exemplifies pyrazine in Compound 3-8 ([0062]).
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 Thompson as modified by Luo and Noboru by substituting the pyridine group at the position corresponding to the ring C of Formula (IX) of Thompson with pyrazine, as taught by Thompson and Noboru.
The motivation for doing so would have been to provide the compound with more bonds with the central metal than a bidentate ligand such that energy transfer between the metal and the ligand is easy, highly efficient light emission is provided, and a larger stabilization energy associated with the formation of the complex is enabled based on the teaching of Thompson and Noboru.
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 pyridine with pyrazine at the position corresponding to the ring C of Formula (IX) of Thompson 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 Thompson as modified by Luo and Noboru (2).
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Claims 1, 4, 7, 9, 13-15, 18, 20, and 31-32 are rejected under 35 U.S.C. 103 as being unpatentable over Thompson et al. (WO 2005/113704 A2).
Regarding claims 1, 4, 7, 9, 13-15, 18, 20, and 31-32, Thompson discloses a compound represented by Formula III used as the emissive material for an organic light emitting device ([0003], [0233]) and exemplifies a compound ([0252], the 8th compound on page 88, hereafter Compound p88-8; and see the pyridine ring in the figure below).
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The Compound p88-8 of Thompson has triazole carbene donors (i.e. the parts enclosed by dashed circles in the figure above) corresponding to the structures of R1-Y1-Y2-R3 and R2-Z1-Z2-R4 of Formula III of Thompson, which does not read on the limitation of the rings A and B of Applicant’s Formula I of the instant claims.
However, Thompson does teach that Y1 can be N; Y2 can be C; R1 and R3 can be linked to form a 6-mebmered cyclic group; Z1 can be N; Z2 can be C; and R2 and R4 can be linked to form a 6-mebmered cyclic group ([0233]). Thompson teaches that Y2 and Z2 can be each a carbene donor ([0236]) and exemplifies a pyridine carbene
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as the carbene donor ([0294]). Thompson further teaches the structure of the 6-membered carbene donor coordinating a metal M,
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(Table 38 on page 365).
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 p88-8 of Thompson by substituting each of the triazole carbene donors with a pyridine carbene donor
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, as taught by Thompson.
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 5-membered triazole carbene donor with 6-membered pyridine carbene donor are exemplified carbene donors. The substitution of triazole carbene with pyridine carbene at the position corresponding to R1-Y1-Y2-R3 and R2-Z1-Z2-R4 of the Formula III of Thompson 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 Thompson (2).
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The Modified compound of Thompson (2), meeting all the limitations of claims 1, 4, 7, 9, and 31-32.
Thompson does not disclose a specific organic light emitting device comprising the Modified compound of Thompson (2); however, Thompson does teach that the compound of Formula III of Thompson is used as the emissive material ([0014], [0233]). Thompson teaches the compound of the invention can be a dopant ([0142]).
Thompson teaches the structure of an organic light emitting device comprising an anode, an emissive layer, and a cathode (Fig. 1, [0117]). Thompson teaches the emissive layer includes an emissive material and a host ([0121]). Thompson exemplifies CBP as the host ([0121]).
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 Thompson (2) by incorporating it as a emissive dopant with a host material into the emissive layer of an organic light emitting device, as taught by Thompson.
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 emissive dopants in an organic light emitting device 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 Thompson (2) comprising an anode, an emissive layer (the Modified Compound of Thompson (2) as an emissive dopant, CBP as a host), and a cathode, wherein the emissive layer material is a formulation, meeting all the limitations of claims 13-15, and 20.
Thompson does not disclose a specific consumer product comprising the Modified organic light emitting device of Thompson (2); however, Thompson does teach the organic light emitting device of Thompson can be incorporated into a consumer product including flat panel displays ([0136]).
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 Thompson (2) by incorporating it into a consumer product, flat panel displays, as taught by Thompson.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, substitution of organic light emitting devices in a consumer product would have been substitution of 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 Thompson (2), meeting all the limitations of claim 18.
Claims 1, 4, 7, 9-10, 13-14, 18, 20, 31, and 33 are rejected under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1, hereafter Djurovich) in view of Liu et al. (“Organic light-emitting devices based on a highly robust osmium(II) complex”, J. Appl. Phys. 2006, vol. 100, page 094508-1 to -4, hereafter Liu) and Thompson et al. (WO 2005/113704 A2, hereafter Thompson).
Regarding claims 1, 4, 7, 9-10, 13-14, 18, 20, 31, and 33, Djurovich discloses a compound having the following structure (the first structure in [0014]; hereafter Formula 014-1).
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Wherein M is a metal; R1 and R2 can be hydrogen, alkyl, or substituted or unsubstituted heteroaryl; (X-Y) can be an ancillary ligand; a is 0-4; m is 1 to maximum number of ligands that may be attached to metal M; m + n is the maximum number of ligands that may be attached to metal M ([0018]).
Djurovich teaches Os as the metal M ([0064]), hydrogen as R1 ([0018]; and phenyl pyridine ligand in [0059]), pyridine as the heteroaryl group ([0073]), and methyl and tert-butyl as the alkyl group ([0066]).
Djurovich does not exemplifies a specific compound structure wherein M is Os, R1 and R2 are each hydrogen; however, Djurovich does teach Os as the metal M ([0064], claim 42), hydrogen as R1 and R2 (substituents of the phenyl pyridine ligand in [0018], [0059]), and variable a of each pyridine and phenyl ring being 4 (number of substituents of the phenyl pyridine ligand in [0059]).
Liu teaches that Os(II) central metal provides shorter triplet-state exciton lifetime due to the enhancement of the heavy-metal atom participating in the lowest excited triplet manifolds (page 1, col. 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 Formula 014-1 of Djurovich by selecting M to be Os; R1 and R2 to be hydrogen; a to be 4, as taught by Djurovich.
The motivation of doing so would have been to provide shorter triplet-state exciton lifetime due to the enhancement of the heavy-metal atom participating in the lowest excited triplet manifolds based on the teaching of Liu.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Each substitution of the structures at the positions corresponding to M, R1, R2, and a in the Formula 014-1 of Djurovich would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Each selection of exemplified structures at the positions corresponding to M, R1, R2, and a in the Formula 014-1 of Djurovich (i.e. Os as M, H as R1, H as R2, and 4 as a) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides the Compound of Djurovich as modified by Liu as shown below.
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Djurovich does not disclose a specific tridentate ligand; however, Djurovich does teach that a substituent can be added to the compound of Djurovich such that the compound can be linked to form a multidentate ligand. Djurovich further teaches that this type of linking can increase stability relative to unlinked structure ([0054]).
Djurovich teaches that the substituent, R2 of Formula 014-1 can be a heteroaryl group ([0018]) and exemplifies pyridine as the heteroaryl group ([0073]).
A pyridine ring as a part of tridentate ligand of an Os(II) complex is known in the art at the time when the invention was effectively filed as taught by Thompson.
Thompson discloses an Os complex comprising a tridentate ligand and used as an emissive material in an organic light emitting device ([0003], [0233]).
Thompson exemplifies a tridentate ligand wherein a phenyl imidazole carbene ligand is substituted by a pyridine ring to comprise a tridentate ligand ([0252], the 4th compound on page 88, hereafter Compound p88-4; and see the pyridine ring in the figure below).
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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 Djurovich as modified by Liu by substituting hydrogen at the substitution position 5 of the phenyl ring (see the substitution positions 1-6 in the figure above) with a pyridine group, as taught by Djurovich and Thompson.
The motivation of doing so would have been to increase stability relative to unlinked structure based on the teaching of Djurovich.
Furthermore, pyridine is a known substituent as a part of the tridentate ligand of an Os complex as taught by Thompson. Pyridine at the position corresponding to the R2 of Formula 014-1 of Djurovich is one of exemplified substituent groups. Thus, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Additionally, the substitution of hydrogen with pyridine at the position corresponding to the R2 of Formula 014-1 of Djurovich 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 Djurovich as modified by Liu and Thompson.
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The ligand LA (the tridentate ligand of the compound) of Compound of Djurovich as modified by Liu and Thompson has identical structure as Formula I of claim 1, meeting all the limitations of claims 1, 4, 7, 9-10, 31, and 33.
Djurovich in view of Liu and Thompson does not disclose a specific organic light emitting device comprising a Compound of Djurovich as modified by Liu and Thompson; however, Djurovich does teach that the compound of Djurovich can comprise the organic layer between a cathode and an anode of an organic light emitting device (Abstract, claim 6).
Djurovich further exemplifies an organic light emitting device comprising anode (ITO), an emission layer comprising mCP as a host and a compound of Djurovich (dopant A) used as an emissive dopant, and a cathode (Al) (Example 1 in [0100]- [0101]).
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 of Djurovich as modified by Liu and Thompson by incorporating it as the emissive dopant of the emission layer of an organic light emitting device of Djurovich, as taught by Djurovich.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, substitution of the emissive dopants of Djurovich in the organic light emitting device of Djurovich would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The resultant device comprises anode (ITO), an emission layer comprising mCP as a host and Compound of Djurovich as modified by Liu and Thompson as an emissive dopant, and a cathode (Al), wherein the emission layer is an organic layer, wherein the host mCP comprises carbazole; and the emissive layer materials are a formulation, meeting all the limitations of claims 13-14, and 20.
Djurovich in view of Liu and Thompson does not disclose a specific consumer product comprising the Organic light emitting device of Djurovich as modified by Liu and Thompson; however, Djurovich does teach the device in accordance with embodiment of the invention can be incorporated into a consumer product including a flat panel display ([0055]).
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 Djurovich as modified by Noboru by incorporating it into a flat panel display, as taught by Djurovich.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, substitution of organic light emitting devices of Djurovich in the flat panel display of Djurovich would have been substitution of one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides a flat panel display comprising an organic light emitting device of Liu and Thompson, wherein the flat panel display is a consumer product, meeting all the limitations of claim 18.
Claims 13-15 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Liu et al. (“Organic light-emitting devices based on a highly robust osmium(II) complex”, J. Appl. Phys. 2006, vol. 100, page 094508-1 to -4) and Thompson et al. (WO 2005/113704 A2) as applied to claims 1, 4, 7, 9-10, 13-14, 18, 20, 31, and 33 above, further in view of Adamovich et al. (US 2013/0112952 A1, hereafter Adamovich).
Regarding claims 13-15 and 20, the Organic light emitting device of Djurovich as modified by Liu and Thompson reads on all the features of claim 13, as outlined above.
The device comprises anode (ITO), an emission layer comprising mCP as a host and Compound of Djurovich as modified by Liu and Thompson as an emissive dopant, and a cathode (Al), wherein the emission layer is an organic layer.
The host compound of mCP does not meet the limitations of claims 15 and 17.
Adamovich discloses an organic light emitting device wherein the emissive layer comprising a host (“organic composition” comprising a first compound and a second compound) and a phosphorescent emissive dopant ([0035] and [0099]).
Adamovich exemplifies a host comprising the following triphenylene containing benzo-fused thiophene compound (Compound H9 of [0070]).
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Adamovich teaches that an organic light emitting device comprising the host provides improved lifetime and efficiency (Abstract and [0001]).
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 Djurovich as modified by Liu and Thompson by substituting the host of the emission layer with the Compound H9 of Adamovich, based on the teaching of Adamovich.
The motivation for doing so would have been to provide the organic light emitting device comprising the benzo-fused thiophene host compound with improved lifetime and efficiency.
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 host compounds would have been one known element for another known element and led to predictable results. See MPEP 2143(I)(B).
The modification provides an organic light emitting device comprising anode (ITO), an emission layer comprising benzo-fused thiophene compound (Compound H9 of Adamovich) as a host and Compound of Djurovich as modified by Liu and Thompson as an emissive dopant, and a cathode (Al), wherein the emission layer is an organic layer; and the emission layer material is equated with a formulation.
Claim 29 is rejected under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Liu et al. (“Organic light-emitting devices based on a highly robust osmium(II) complex”, J. Appl. Phys. 2006, vol. 100, page 094508-1 to -4) and Thompson et al. (WO 2005/113704 A2) as applied to claims 1, 4, 7, 9-10, 13-14, 18, 20, 31, and 33 above, further in view of Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective”, ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo).
Regarding claim 29, the Compound of Djurovich as modified by Liu and Thompson reads on all the features of claim 1, as outlined above.
The Compound of Djurovich as modified by Liu and Thompson does not substituents other than hydrogen at the positions corresponding to the R1 to R3 of Applicant’s Formula I; however, Djurovich does teach that the R2 of Formula 014-1 of Djurovich can be alkyl ([0018]). Djurovich exemplifies tert-butyl as the alkyl group ([0066]).
Luo teaches that a steric bulky group such as a tert-butyl of a transition metal complex can effectively suppress intermolecular interactions to improve the efficiency and the color purity of the organic light emitting device comprising the metal complex (page 69, column 2, paragraph 1). Luo exemplifies complexes wherein the phenyl ring coordinating to the metal center is substituted by a t-butyl group at the para position with respect to the carbon coordinating to the metal (Pt-1 to Pt-3 in Scheme 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 of Djurovich as modified by Liu and Thompson by substituting the para hydrogen atom substituted to the phenyl ring of the tridentate ligand with a tert-butyl group, as taught by Djurovich and Luo.
The motivation for doing so would have been to effectively suppress intermolecular interactions to improve the efficiency and the color purity of the organic light emitting device comprising the metal complex, based on the teaching of Luo.
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 a tert-butyl group at the position corresponding to the R2 of Formula 014-1 of Djurovich 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 the Compound of Djurovich as modified by Liu, Thompson, and Luo.
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Claims 1, 4, 7, 9-10, 13-14, 18, 20, 29, 31, and 33 are rejected under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Noboru et al. (WO 2006/100925, a machine translated English document is referred to, hereafter Noboru) and Wilkinson et al. (“Luminescent Complexes of Iridium(III) Containing N^C^N-Coordinating Terdentate Ligands”, Inorg. Chem. 2006, vol. 45, page 8685-8699, hereafter Wilkinson).
Regarding claims 1, 4, 7, 9-10, 13-14, 18, 20, 29, 31, and 33, Djurovich discloses a compound having the following structure (the first structure in [0014]; hereafter Formula 014-1).
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Wherein M is a metal; R1 and R2 can be hydrogen, alkyl, or substituted or unsubstituted heteroaryl; (X-Y) can be an ancillary ligand; a is 0-4; m is 1 to maximum number of ligands that may be attached to metal M; m + n is the maximum number of ligands that may be attached to metal M ([0018]).
Djurovich exemplifies Ir as the metal M ([0064]; dopant A in [0112]), hydrogen as R1 ([0018]; phenyl pyridine ligand in [0059]), pyridine as the heteroaryl group ([0073]), and methyl as the alkyl group ([0066]).
Djurovich does not exemplifies a specific compound structure wherein M is Ir, R1 and R2 are each hydrogen; however, Djurovich does teach Ir as the metal M ([0064]; Ir as the metal center of dopant A in [0112]), hydrogen as R1 and R2 (substituents of the phenyl pyridine ligand in [0018], [0059]), and a of each pyridine and phenyl ring being 4 (number of substituents of the phenyl pyridine ligand in [0059]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified Formula 014-1 of Djurovich by selecting M to be Ir; R1 and R2 to be hydrogen; a to be 4, as taught by Djurovich.
The substitution of the structures at the positions corresponding to M, R1, R2, and a in the Formula 014-1 of Djurovich would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Each selection of exemplified structures at the positions corresponding to M, R1, R2, and a in the Formula 014-1 of Djurovich (i.e. Ir as M, H as R1, H as R2, and 4 as a) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides the Modified compound of Djurovich as shown below.
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Djurovich does not disclose a specific tridentate ligand; however, Djurovich does teach that a substituent can be added to the compound of Djurovich such that the compound can be linked to form a multidentate ligand. Djurovich further teaches that this type of linking can increase stability relative to unlinked structure ([0054]).
Djurovich teaches that the substituent, R2 of Formula 014-1 can be a heteroaryl group ([0018]) and exemplifies pyridine as the heteroaryl group ([0073]).
Noboru discloses an Ir complex comprising tridentate ligands used for the emitting layer material of an organic light emitting device ([0019]- [0028]).
Noboru teaches that a tridentate ligand has more bonds with the central metal than a bidentate ligand such as a phenyl pyridine ligand such that energy transfer between the metal and the ligand is easy, provides highly efficient light emission, and enables to obtain a larger stabilization energy associated with the formation of the complex ([0036]).
Noboru exemplifies a pyridine group substituted to the bidentate ligand of phenyl pyridine to form a tridentate ligand ([0053]; and multiple examples including Compounds 1-1, 2-2, 2-3, 2-8, 3-4, 3-7 in [0057]).
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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 Djurovich by substituting hydrogen at the substitution position 5 of the phenyl ring (see the substitution positions 1-6 in the figure of the Modified compound of Djurovich above) with a pyridine group, as taught by Djurovich and Noboru.
The motivation for doing so would have been to provide the compound with more bonds with the central metal than a bidentate ligand such that energy transfer between the metal and the ligand is easy, highly efficient light emission is provided, and a larger stabilization energy associated with the formation of the complex is enabled based on the teaching of Noboru.
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). A pyridinyl group as R2 of Formula 014-1 of Djurovich is one of exemplified substituent groups. The substitution of hydrogen with pyridine would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of the pyridinyl group at R2 would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The resultant compound has identical structure as the Modified compound of Djurovich above except that a pyridinyl group is substituted at the position 5 of the phenyl ring (see the substitution positions 1-6 in the figure of the Modified compound of Djurovich above).
The resultant compound does not have an alkyl substituent at the position corresponding to the R2 of Applicant’s Formula I; however, Djurovich does teach that R2 of Formula 014-1 of Djurovich can be alkyl ([0018]). Djurovich exemplifies t-butyl as the alkyl group ([0066]).
Noboru teaches that bulky substituents allows the metal to selectively tridentate with the ligand and prevent the formation of unwanted bidentate complexes ([0049]).
Noboru exemplifies a t-butyl group at the substitution position corresponding to the substituent of X6 of Applicant’s Formula I (multiple examples including Compound 1-5 in [0057]).
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 Djurovich as taught by Noboru by substituting a t-butyl group at the position corresponding to the substituent of X6 of Applicant’s Formula I, as taught by Djurovich and Noboru.
The motivation for doing so would have been to allow the metal of the compound to selectively form tridentate with the ligand and prevent the formation of unwanted bidentate complexes based on the teaching of Noboru.
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). A t-butyl group as R2 of Formula 014-1 of Djurovich is one of exemplified substituent groups. The substitution of hydrogen with t-butyl would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of the t-butyl group at R2 would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The resultant compound has following structure.
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The Compound of Djurovich as modified by Noboru does not have a tridentate ligand LB; however, Djurovich does teach that in the Formula 014-1 of Djurovich, the (X-Y) can be an ancillary ligand; m is 1 to maximum number of ligands that may be attached to metal M; m + n is the maximum number of ligands that may be attached to metal M ([0018]).
Djurovich teaches that a substituent can be added to the compound of Djurovich such that the compound can be linked to form a multidentate ligand. Djurovich further teaches that this type of linking can increase stability relative to unlinked structure ([0054]).
Noboru discloses an Ir complex comprising tridentate ligands used for the emitting layer material of an organic light emitting device ([0019]- [0028]).
Noboru teaches that a tridentate ligand has more bonds with the central metal than a bidentate ligand such as a phenyl pyridine ligand such that energy transfer between the metal and the ligand is easy, provides highly efficient light emission, and enables to obtain a larger stabilization energy associated with the formation of the complex ([0036]).
Djurovich as modified by Noboru does not exemplifies a specific tridentate ancillary ligand having same structure as the ligand LB of the instant claims 11 or 21.
Wilkinson teaches that two tridentate ligands can coordinate to the Ir metal ion wherein one is a monoanionic tridentate ligand and the other is a dianionic tridentate ligand to keep the overall charge neutrality (page 8687, column 1, the first paragraph under “Result and Discussion”).
Wilkinson exemplifies a tridentate ligand dppy wherein the compound has m and n being each 1 (the top ligand of Compound 3 in Scheme 5).
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 Djurovich as modified by Noboru by substituting the ancillary ligand (X-Y) with the ligand dppy of Wilkinson with m and n being each 1, as taught by Djurovich, Noboru, and Wilkinson.
The motivation for doing so would have been to increase stability, provide the compound with more bonds with the central metal than a bidentate ligand such that energy transfer between the metal and the ligand is easy, highly efficient light emission is provided, and a larger stabilization energy associated with the formation of the complex is enabled, and keep the overall charge neutrality, based on the teachings of Djurovich, Noboru, and Wilkinson.
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 resultant compound has the following structure.
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The Compound of Djurovich as modified by Noboru and Wilkinson, meeting all the limitations of claims 1, 4, 7, 9-10, 29, 31, and 33.
Djurovich as modified by Noboru and Wilkinson does not disclose a specific organic light emitting device comprising a Compound of Djurovich as modified by Noboru and Wilkinson; however, Djurovich does teach that the compound of Djurovich can comprise the organic layer between a cathode and an anode of an organic light emitting device (Abstract, claim 6).
Djurovich further exemplifies an organic light emitting device comprising anode (ITO), an emission layer comprising mCP as a host and a compound of Djurovich (dopant A) used as an emissive dopant, and a cathode (Al) (Example 1 in [0100]- [0101]).
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 of Djurovich as modified by Noboru and Wilkinson by substituting the emissive dopant of the emission layer of an organic light emitting device of Djurovich (Example 1) with the Compound of Djurovich as modified by Noboru and Wilkinson, as taught by Djurovich.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, both dopant A and the compound of Djurovich as modified by Noboru and Wilkinson are encompassed by the compound of Djurovich represented by Formula 014-1. The substitution of the compounds of Djurovich in the device of Djurovich would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The resultant device comprises anode (ITO), an emission layer comprising mCP as a host and Compound of Djurovich as modified by Noboru and Wilkinson as an emissive dopant, and a cathode (Al), wherein the emission layer materials are equated with a formulation, meeting all the limitations of claims 13-14, and 20.
Djurovich as modified by Noboru and Wilkinson does not disclose a specific consumer product comprising the organic light emitting device of Djurovich as modified by Noboru and Wilkinson; however, Djurovich does teach the device in accordance with embodiment of the invention can be incorporated into a consumer product including a flat panel display ([0055]).
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 Djurovich as modified by Noboru and Wilkinson by incorporating it into a flat panel display, as taught by Djurovich.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, substitution of organic light emitting devices of Djurovich in the flat panel display of Djurovich would have been substitution of one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides a flat panel display comprising an organic light emitting device of Djurovich as modified by Noboru and Wilkinson, wherein the flat panel display is a consumer product, meeting all the limitations of claim 18.
Claims 13-15 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Djurovich et al. (US 2005/0258433 A1) in view of Noboru et al. (WO 2006/100925, a machine translated English document is referred to) and Wilkinson et al. (“Luminescent Complexes of Iridium(III) Containing N^C^N-Coordinating Terdentate Ligands”, Inorg. Chem. 2006, vol. 45, page 8685-8699) as applied to claims 1, 4, 7, 9-10, 13-14, 18, 20, 29, 31, and 33 above, further in view of Adamovich et al. (US 2013/0112952 A1).
Regarding claims 13-15 and 20, the organic light emitting device of Djurovich as modified by Noboru and Wilkinson reads on all the features of claim 13, as outlined above.
The device comprises anode (ITO), an emission layer comprising mCP as a host and Compound of Djurovich as modified by Noboru and Wilkinson as an emissive dopant, and a cathode (Al), wherein the emission layer is an organic layer.
The host compound of mCP does not meet the limitations of claims 15 and 17.
Adamovich discloses an organic light emitting device wherein the emissive layer comprising a host (“organic composition” comprising a first compound and a second compound) and a phosphorescent emissive dopant ([0035] and [0099]).
Adamovich exemplifies a host comprising the following triphenylene containing benzo-fused thiophene compound (Compound H9 of [0070]).
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Adamovich teaches that an organic light emitting device comprising the host provides improved lifetime and efficiency (Abstract and [0001]).
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 Djurovich as modified by Noboru and Wilkinson by substituting the host of the emission layer with the Compound H9 of Adamovich, based on the teaching of Adamovich.
The motivation for doing so would have been to provide the organic light emitting device comprising the benzo-fused thiophene host compound with improved lifetime and efficiency.
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). Furthermore, both mCP and Compound H9 are known host compounds. Substitution of host compounds would have been one known element for another known element and led to predictable results. See MPEP 2143(I)(B).
The modification provides an organic light emitting device comprising anode (ITO), an emission layer comprising benzo-fused thiophene compound (Compound H9 of Adamovich) as a host and Compound of Djurovich as modified by Noboru and Wilkinson as an emissive dopant, and a cathode (Al), wherein the emission layer is an organic layer; and the emission layer material is equated with a formulation.
Claim Objections/Allowable subject matter
Claim 30 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
As outlined above, Djurovich is a representation of the closest prior arts. As described in more detail above, Djurovich teaches Ir and Os complexes each comprising a 6-membered carbene containing ligand each of which reads on the limitations of the ligand LA of Formula I of the instant claim 1.
However, claim 30 additionally requires the metal M to be Pt.
While Djurovich generally teaches the metal center of the complexes of Djurovich can be Pt ([0064]), Djurovich in combination of teaching references does not teach a specific Pt complex wherein the ligand has identical structure as LA of Formula I of the instant claim 1, as required in the instant claim 30.
As outlined above, Thompson is a representation of the closest prior arts. As described in more detail above, Thompson teaches an Os complex comprising a 6-membered carbene containing ligand which reads on the limitations of the ligand LA of Formula I of the instant claim 1.
However, claim 30 additionally requires the metal M to be Pt.
Thompson even in combination of teaching references does not teach a specific Pt complex wherein the ligand has identical structure as LA of Formula I of the instant claim 1, as required in the instant claim 30.
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.
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/SEOKMIN JEON/Primary Examiner, Art Unit 1786