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 .
Response to Amendment
The amendment of 10/27/2025 has been entered.
Disposition of claims:
Claims 4-7 has been canceled.
Claims 1-3 and 8-20 are pending.
Claims 1, 13, and 15 have been amended.
The amendments of claims 1, 13, and 15 have overcome:
the rejections of claims 1-3 and 8-19 under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 2019/0326527 A1, hereafter Choi) in view of Shang et al. (“DFT/TDDFT study on the electronic structures and optoelectronic properties of a series of iridium(III) complexes based on quinoline derivatives in OLEDs”, J. Phys. Org. Chem. 2013, vol. 26, page 784-790, hereafter Shang) and Boudreault et al. (US 2015/0001472 A1, hereafter Boudreault),
the rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 2019/0326527 A1) in view of Shang et al. (“DFT/TDDFT study on the electronic structures and optoelectronic properties of a series of iridium(III) complexes based on quinoline derivatives in OLEDs”, J. Phys. Org. Chem. 2013, vol. 26, page 784-790) and Boudreault et al. (US 2015/0001472 A1) as applied to claims 1-3 and 8-19 above, further in view of Pang et al. (“A full-color, low-power, wearable display for mobile applications”, SPIE, 03/29/2012, hereafter Pang),
the rejections of claims 1-3, 8, and 10-19 under 35 U.S.C. 103 as being unpatentable over Lin et al. (US 2017/0155065 A1, hereafter Lin) in view of Shang et al. (“DFT/TDDFT study on the electronic structures and optoelectronic properties of a series of iridium(III) complexes based on quinoline derivatives in OLEDs”, J. Phys. Org. Chem. 2013, vol. 26, page 784-790, hereafter Shang) and Boudreault et al. (US 2015/0001472 A1),
the rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Lin et al. (US 2017/0155065 A1) in view of Shang et al. (“DFT/TDDFT study on the electronic structures and optoelectronic properties of a series of iridium(III) complexes based on quinoline derivatives in OLEDs”, J. Phys. Org. Chem. 2013, vol. 26, page 784-790, hereafter Shang) and Boudreault et al. (US 2015/0001472 A1) as applied to claims 1-3, 8, and 10-19 above, further in view of Pang et al. (“A full-color, low-power, wearable display for mobile applications”, SPIE, 03/29/2012, hereafter Pang),
the rejections of claims 1-3, 9-14, and 16-19 under 35 U.S.C. 103 as being unpatentable over Shen et al. (US 2007/0237981 A1, hereafter Shen) in view of Kurotaki et al. (JP 2005/213348 A, machine translated English version is referred to, hereafter Kurotaki),
the rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Shen et al. (US 2007/0237981 A1) in view of Kurotaki et al. (JP 2005/213348 A, machine translated English version is referred to), as applied to claims 1-3, 9-14, and 16-19 above, further in view of Pang et al. (“A full-color, low-power, wearable display for mobile applications”, SPIE, 03/29/2012, hereafter Pang) set forth in the last Office Action.
The rejections have been withdrawn.
Response to Arguments
Applicant’s arguments see page 26-28 of the reply filed 04/29/2026 regarding the rejections of claims 1-3 and 8-19 under 35 U.S.C. 103 as being unpatentable over Choi/Shang/Boudreault, the rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Choi/Shang/Boudreault/Pang set forth in the Office Action of 02/10/2026 have been considered.
Applicant argues that amended claims are nonobvious over the combination of the cited references.
The rejections refer to the Compound of Choi as modified by Shang and Boudreault (see section 72 of the last Office Action). The compound does not read on the limitation of the Formula 1 of the amended claims because at least the unsubstituted phenyl group does not read on the limitation of the R13 of Applicant’s Formula 11-1. Thus, the rejections are withdrawn.
Applicant’s arguments see page 28-30 of the reply filed 04/29/2026 regarding the rejections of claims 1-3, 8, and 10-19 under 35 U.S.C. 103 as being unpatentable over Lin/Shang/Boudreault, the rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Lin/Shang/Boudreault/Pang set forth in the Office Action of 02/10/2026 have been considered.
Applicant argues that amended claims are nonobvious over the combination of the cited references.
The rejections refer to the Compound of Lin as modified by Shang and Boudreault (see section 108 of the last Office Action). The compound does not read on the limitation of the Formula 1 of the amended claims because at least the left ligand does not read on the limitation of Applicant’s Formula 11-1. Thus, the rejections are withdrawn.
Applicant’s arguments see page 30-334 of the reply filed 04/29/2026 regarding the rejections of claims 1-3, 9-14, and 16-19 under 35 U.S.C. 103 as being unpatentable over Shen/Kurotaki, the rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Shen/Kurotaki/Pang set forth in the Office Action of 02/10/2026 have been considered.
Applicant argues that amended claims are nonobvious over the combination of the cited references.
The rejections refer to the Compound of Shen as modified by Kurotaki (2) and the Compound of Shen as modified by Kurotaki and Boudreault (see sections 139 and 172 of the last Office Action). The compounds do not read on the limitation of the Formula 1 of the amended claims because at least the perylene ring does not read on the limitation of the phenanthrene ring of Applicant’s Formula 11-1. Thus, the rejections are withdrawn.
However, Shen is still applicable for new grounds of rejection.
Shen discloses an organometallic compound (Formula (I) in [0005]) used for an organic light emitting device ([0001]) and exemplifies Compound 2 ([0020]).
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In the Compound 2 of Shen, the phenyl group at the position corresponding to the A2 of the Formula (I) of Shen does not read on the limitation of Applicant’s Formula 11-1; however, Shen does teach that the A2 can be a substituted or non-substituted aryl group ([0005]).
Edkins discloses a pyrene-containing Ir metal complex (Ir(2-pypyr)2(acac) in Scheme 1, Abstract). It is known in the art that Ir(ppy)2(acac) emits green light. Edkins teaches that Ir(2-pypyr)2(acac) emits red emission (Fig. 5), indicating that substitution of the phenyl ring of the phenyl pyridine-based ligand with pyrene, otherwise same, provides a red shift in the emission spectrum. Edkins further teaches that an Ir complex comprising 1-pypyr has unfavorable steric interaction and provides nonradiative deactivation (page 9858, column 2, line 3-6); thus, an ordinary skill in the art would choose 2-pypyr instead of 1-pypyr when forming a pyrene-containing Ir complex.
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound 2 of Shen by substituting the phenyl group at the position corresponding to A2 of Formula (I) of Shen with pyrene (i.e. 2-pyrene).
The motivation of doing so would have been to red shift the emission spectrum with reduced nonradiative deactivation, based on the teaching of Edkins.
The modification provides Compound of Shen as modified by Edkins.
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In the Compound of Shen as modified by Edkins, the ligand at the position corresponding to the A3 of Formula (I) of Shen is acetylacetonate which does not read on the limitation of claim 9; however, Shen does teach that the ligand at the A3 can be a picolinic acid ligand ([0011]).
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Shen as modified by Edkins by substituting the acetylacetonate ligand with a picolinic acid ligand as taught by Shen.
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The modification provides Compound of Shen as modified by Edkins (2) which has identical structure as Applicant’s Formula 1.
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 1-3, 9-14, and 16-19 are rejected under 35 U.S.C. 103 as being unpatentable over Shen et al. (US 2007/0237981 A1, hereafter Shen) in view of Edkins et al. (“Syntheses, Structures, and Comparison of the Photophysical Properties of Cyclometalated Iridium Complexes Containing the Isomeric 1- and 2‑(2′-pyridyl)pyrene Ligands” Inorg. Chem. 2013, vol. 52, page9842-9860, hereafter Edkins).
Regarding claims 1-3, 9-14, and 16-19, Shen discloses an organometallic compound (Formula (I) in [0005]) used for an organic light emitting device ([0001]) and exemplifies Compound 2 ([0020]).
Shen exemplifies an organic light emitting device ([0021]-[0022], column 3 in Table 1) comprising a first electrode (anode, ITO), a hole transport layer (NPB), an emission layer (Compound 2 as a dopant and CBP as a host with dopant/host volumetric ratio of 6%), an electron transport layer (Alq3), and a second electrode (cathode, Al).
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In the Compound 2 of Shen, the phenyl group at the position corresponding to the A2 of the Formula (I) of Shen does not read on the limitation of Applicant’s Formula 11-1; however, Shen does teach that the A2 can be a substituted or non-substituted aryl group ([0005]).
Edkins discloses a pyrene-containing Ir metal complex (Ir(2-pypyr)2(acac) in Scheme 1, Abstract). It is known in the art that Ir(ppy)2(acac) emits green light. Edkins teaches that Ir(2-pypyr)2(acac) emits red emission (Fig. 5), indicating that substitution of the phenyl ring of the phenyl pyridine-based ligand with pyrene, otherwise same, provides a red shift in the emission spectrum. Edkins further teaches that an Ir complex comprising 1-pypyr has unfavorable steric interaction and provides nonradiative deactivation (page 9858, column 2, line 3-6); thus, an ordinary skill in the art would choose 2-pypyr instead of 1-pypyr when forming a pyrene-containing Ir complex.
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 2 of Shen by substituting the phenyl group at the position corresponding to A2 of Formula (I) of Shen with pyrene (i.e. 2-pyrene), as taught by Shen and Edkins.
The motivation of doing so would have been to red shift the emission spectrum with reduced nonradiative deactivation, based on the teaching of Edkins.
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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In the Compound of Shen as modified by Edkins, the ligand at the position corresponding to the A3 of Formula (I) of Shen is acetylacetonate which does not read on the limitation of claim 9; however, Shen does teach that the ligand at the A3 can be a picolinic acid ligand ([0011]).
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 Shen as modified by Edkins by substituting the acetylacetonate ligand with a picolinic acid ligand as taught by Shen.
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 Shen as modified by Edkins (2), meeting all the limitations of claims 1-3 and 9-14.
It should be noted that the pyrene moiety reads on the substituted phenanthrene moiety of Applicant’s Formula 11-1, wherein R27 and R28 can be each a substituted C2 alkenyl group. While the instant claims are silent about formation of a fused ring between substituents R27 and R28, the instant specification recites “at least two of R21 to R28 are optionally bound to form a carbocyclic group” (page 2, par. 2). The instant claims are interpreted in the broadest reasonable manner (BRI) in light of specification such that the fused carbocyclic ring (i.e. benzene) at positions R27 and R28 reads on all the limitation of the Formula 11-1.
The modification also provides Organic light emitting device of Shen as modified by Edkins comprising a first electrode (anode, ITO), a hole transport layer (NPB), an emission layer (Compound of Shen as modified by Edkins (2) as a dopant and CBP as a host with dopant/host volumetric ratio of 6%), an electron transport layer (Alq3), and a second electrode (cathode, Al), wherein the hole transport layer, the emission layer, and the electron transport layer are an organic layer, meeting all the limitations of claims 16-19.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Shen et al. (US 2007/0237981 A1) in view of Edkins et al. (“Syntheses, Structures, and Comparison of the Photophysical Properties of Cyclometalated Iridium Complexes Containing the Isomeric 1- and 2‑(2′-pyridyl)pyrene Ligands” Inorg. Chem. 2013, vol. 52, page9842-9860) as applied to claims 1-3, 9-14, and 16-19 above, further in view of Pang et al. (“A full-color, low-power, wearable display for mobile applications”, SPIE, 03/29/2012, hereafter Pang).
Regarding claim 20, the Organic light emitting device of Shen as modified by Edkins reads on all the features of claim 16 as outlined above.
The device comprises a first electrode (anode, ITO), a hole transport layer (NPB), an emission layer (Compound of Shen as modified by Edkins (2) as a dopant and CBP as a host with dopant/host volumetric ratio of 6%), an electron transport layer (Alq3), and a second electrode (cathode, Al), wherein the hole transport layer, the emission layer, and the electron transport layer are an organic layer.
Shen in view of Edkins and Boudreault does not disclose a specific display device comprising the Organic light emitting device of Shen as modified by Edkins and Boudreault.
Pang discloses a display device (“flexible active matrix OLED display” in Fig. 3) comprising an organic light emitting device (“C: OLED” in Fig. 3).
Pang teaches the display device provide a full-color, low-power, wearable display for mobile application (title and abstract).
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 Shen as modified by Edkins and Boudreault by incorporating it into a display device, as taught by Shen, Edkins and Boudreault, and Pang.
The motivation of doing so would have been to provide a full-color, low-power, wearable display for mobile application based on the teaching of Pang.
Furthermore, the modification would have been a combination of prior art elements according to known material and method to achieve predictable results. See MPEP 2143(I)(A). The substitution of the organic light emitting devices in a display 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 an electronic apparatus (i.e. display device) comprising the Organic light emitting device of Shen as modified by Edkins.
Claims 1-3, 8, 10-14, and 16-19 are rejected under 35 U.S.C. 103 as being unpatentable over Shen et al. (US 2007/0237981 A1, hereafter Shen) in view of Edkins et al. (“Syntheses, Structures, and Comparison of the Photophysical Properties of Cyclometalated Iridium Complexes Containing the Isomeric 1- and 2‑(2′-pyridyl)pyrene Ligands” Inorg. Chem. 2013, vol. 52, page9842-9860, hereafter Edkins) and Boudreault et al. (US 2015/0001472 A1, hereafter Boudreault).
Regarding claims 1-3, 8, 10-14, and 16-19, Shen discloses an organometallic compound (Formula (I) in [0005]) used for an organic light emitting device ([0001]) and exemplifies Compound 2 ([0020]).
Shen exemplifies an organic light emitting device ([0021]-[0022], column 3 in Table 1) comprising a first electrode (anode, ITO), a hole transport layer (NPB), an emission layer (Compound 2 as a dopant and CBP as a host with dopant/host volumetric ratio of 6%), an electron transport layer (Alq3), and a second electrode (cathode, Al).
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In the Compound 2 of Shen, the phenyl group at the position corresponding to the A2 of the Formula (I) of Shen does not read on the limitation of Applicant’s Formula 11-1; however, Shen does teach that the A2 can be a substituted or non-substituted aryl group ([0005]).
Edkins discloses a pyrene-containing Ir metal complex (Ir(2-pypyr)2(acac) in Scheme 1, Abstract). It is known in the art that Ir(ppy)2(acac) emits green light. Edkins teaches that Ir(2-pypyr)2(acac) emits red emission (Fig. 5), indicating that substitution of the phenyl ring of the phenyl pyridine-based ligand with pyrene, otherwise same, provides a red shift in the emission spectrum. Edkins further teaches that an Ir complex comprising 1-pypyr has unfavorable steric interaction and provides nonradiative deactivation (page 9858, column 2, line 3-6); thus, an ordinary skill in the art would choose 2-pypyr instead of 1-pypyr when forming a pyrene-containing Ir complex.
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 2 of Shen by substituting the phenyl group at the position corresponding to A2 of Formula (I) of Shen with pyrene (i.e. 2-pyrene), as taught by Shen and Edkins.
The motivation of doing so would have been to red shift the emission spectrum with reduced nonradiative deactivation, based on the teaching of Edkins.
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 Shen as modified by Edkins.
The acetylacetonate ancillary ligand does not read on the limitation of Applicant’s Formula 2-1.
Boudreault 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 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 2 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 Shen as modified by Edkins by substituting the acetylacetonate ligand with the ligand LA1 of Boudreault, as taught by Boudreault.
The motivation of doing so would have been to provide smaller FWHM, lower voltage and higher luminous, external quantum, and power efficiencies based on the teaching of Boudreault.
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 Shen as modified by Edkins and Boudreault, meeting all the limitations of claims 1-3, 8, and 10-14.
It should be noted that the pyrene moiety reads on the substituted phenanthrene moiety of Applicant’s Formula 11-1, wherein R27 and R28 can be each a substituted C2 alkenyl group. While the instant claims are silent about formation of a fused ring between substituents R27 and R28, the instant specification recites “at least two of R21 to R28 are optionally bound to form a carbocyclic group” (page 2, par. 2). The instant claims are interpreted in the broadest reasonable manner (BRI) in light of specification such that the fused carbocyclic ring (i.e. benzene) at positions R27 and R28 reads on all the limitation of the Formula 11-1.
The modification also provides Organic light emitting device of Shen as modified by Edkins and Boudreault comprising a first electrode (anode, ITO), a hole transport layer (NPB), an emission layer (Compound of Shen as modified by Edkins and Boudreault as a dopant and CBP as a host with dopant/host volumetric ratio of 6%), an electron transport layer (Alq3), and a second electrode (cathode, Al), wherein the hole transport layer, the emission layer, and the electron transport layer are an organic layer, meeting all the limitations of claims 16-19.
Claim Objections / Allowable Subject Matter
Claim 15 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, Shen is representation of the closest prior art. As described in more detail above, Shen teaches an organometallic compound comprising a ligand containing a phenyl thienopyridine moiety; however, Shen does not teach an organometallic compound having same structure as the specific embodiments of the instant claim 15.
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
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