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 .
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 03/09/2026 was filed after the mailing date of the instant application on 10/04/2022. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Response to Amendment
In the response filed 03/10/2026, the claims and specification were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims and specification, the objections to claims 1, 17, and 19-20 and to the specification are withdrawn by the Office.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 112(b) of claims 1-20 as failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention, the rejection under 35 U.S.C. 112(d) of claims 14 and 19 as being of improper dependent form, the rejection under 35 U.S.C. 102 of claims 1-14 as being anticipated by Park et al. (KR 2013/0110934 A), and the rejections under 35 U.S.C. 103 of claims 15, 17, and 20 as being unpatentable over Park et al. (KR 2013/0110934 A) as applied above, of claim 16 as being unpatentable over Park et al. (KR 2013/0110934 A) as applied above and further in view of Kim et al. (KR 2012/0032054 A), and of claims 18 and 19 as being unpatentable over Park et al. (KR 2013/0110934A) as applied above, and further in view of Metz et al. (US 2016/0072081 A1) are withdrawn by the Office.
Claims 1-20 were filed originally.
Claims 21-25 have been added.
Claims 2, 6, 8, 16, and 19 have been canceled.
Claims 1, 14, 17, and 20 are instantly amended.
Claims 1, 3-5, 7, 9-15, 17-18, and 20-25 remain pending in the application and are examined herein.
Response to Arguments
Applicant’s arguments have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
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, 3-5, 7, 9-15, 17-18, and 20-23 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (US 2016/0141526 A1) in view of Takiguchi et al. (US 2003/0068535 A1).
With respect to claims 1, 3-5, 7, and 9, Lee discloses an organometallic compound for use in an organic electroluminescent device, such as compound 3 (paragraph 0167, page 27), which is pictured below.
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However, Lee does not teach nor fairly suggest that the compound also comprises a polycyclic fused-ring system comprising at least one 5-membered and at least one 6-membered ring.
In analogous art, Takiguchi also teaches organometallic compounds for use in an organic electroluminescent device.
Takiguchi teaches a bidentate ligand comprising two cyclic groups connected by a single bond wherein at least one cyclic group comprises a partial structure of formula (5) (paragraph 0084), which is pictured below.
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In this formula, Y is oxygen (paragraph 0043).
Takiguchi teaches that incorporating the aromatic group of formula (5) into a metal coordination compounds allows for control of the emissive wavelength (particularly to provide a long emission wavelength). Further, the presence of the aromatic group of formula (5) enhances the solubility of the metal coordination compound in an organic solvent, facilitating purification thereof by recrystallization or column chromatography (paragraph 0085). The aromatic group of formula (5) is also able to change the intermolecular interaction of the compound with the host material by suppressing thermal deactivation and formation of exciton associates. This reduces the quenching process and improves phosphorescent yield and device characteristics. For this reason, a metal coordination compound comprising a moiety of formula (5) exhibits excellent stability and continuous current passage (paragraph 0086).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate a moiety of formula (5) into the phenylpyridine ligand of Lee in order to allow for control of the emissive wavelength, enhance the solubility of the metal coordination compound in an organic solvent, facilitate purification thereof by recrystallization or column chromatography, change the intermolecular interaction of the compound with the host material by suppressing thermal deactivation and formation of exciton associate, reduce the quenching process, improve phosphorescent yield and device characteristics, and obtain a compound with excellent stability and continuous current passage (paragraph 0086), as taught by Takiguchi.
Such a modification produces a compound that meets the requirements of instant condition (1)(i) wherein x is 1, y is 2, and z is 0, A is a 6-membered heterocyclic (pyridine) ring, B is a 6-membered carbocyclic (benzene) ring, C is a 6-membered heterocyclic (pyridine) ring, D is a fused 6-membered carbocyclic and 5-membered heterocyclic (benzofuran) ring, Z1, Z3, Z4, Z5, Z7, and Z8 are a carbon atom, Z2 and Z6 are a nitrogen atom, K is a direct bond, one of RA is a C1 alkyl (methyl) group and one of RA is represented by Formula III, X1 through X5 are each a carbon atom, L is a direct bond, Q is a silicon atom, R1 through R3 are each a C1 alkyl (methyl) group, two RD are joined to form a fused benzene group, and RB and RC are not present.
With respect to claims 10 and 11, Lee and Takiguchi teach the compound of claim 1, and ligand LA is represented by the first embodiment of each claim, as pictured above.
With respect to claim 12, Lee and Takiguchi teach the compound of claim 1, and the compound is represented by instant ligand LA1(L1)(Q1)(R2)(R3)(R1)(R1)(R1)(R1), as pictured above.
With respect to claim 13, Lee and Takiguchi teach the compound of claim 1, and the compound has the formula Ir(LA)(LB)2, as discussed above.
With respect to claim 14, Lee and Takiguchi teach the compound of claim 1, and LB is represented by the embodiment of the instant claim found in the second row, second column when K1’ is a direct bond, Y’ is an oxygen atom, and all other Y characters are carbon atoms, as discussed above. Ligand LC is not present.
With respect to claim 15, Lee and Takiguchi teach the compound of claim 1, and the compound has the formula Ir(LA)(LB)2, wherein LA is as discussed above and LB is instant LB65, as discussed above. Ligand LC is not present.
With respect to claim 17, Lee discloses an organic light emitting device (OLED) comprising an anode, a cathode (paragraph 0181), and an organic layer between the anode and cathode, and the organic layer comprises (paragraph 0172) an organometallic compound for use in an organic electroluminescent device, such as compound 3 (paragraph 0167, page 27), which is pictured below.
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However, Lee does not teach nor fairly suggest that the compound also comprises a polycyclic fused-ring system comprising at least one 5-membered and at least one 6-membered ring.
In analogous art, Takiguchi also teaches organometallic compounds for use in an organic electroluminescent device.
Takiguchi teaches a bidentate ligand comprising two cyclic groups connected by a single bond wherein at least one cyclic group comprises a partial structure of formula (5) (paragraph 0084), which is pictured below.
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In this formula, Y is oxygen (paragraph 0043).
Takiguchi teaches that incorporating the aromatic group of formula (5) into a metal coordination compounds allows for control of the emissive wavelength (particularly to provide a long emission wavelength). Further, the presence of the aromatic group of formula (5) enhances the solubility of the metal coordination compound in an organic solvent, facilitating purification thereof by recrystallization or column chromatography (paragraph 0085). The aromatic group of formula (5) is also able to change the intermolecular interaction of the compound with the host material by suppressing thermal deactivation and formation of exciton associates. This reduces the quenching process and improves phosphorescent yield and device characteristics. For this reason, a metal coordination compound comprising a moiety of formula (5) exhibits excellent stability and continuous current passage (paragraph 0086).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate a moiety of formula (5) into the phenylpyridine ligand of Lee in order to allow for control of the emissive wavelength, enhance the solubility of the metal coordination compound in an organic solvent, facilitate purification thereof by recrystallization or column chromatography, change the intermolecular interaction of the compound with the host material by suppressing thermal deactivation and formation of exciton associate, reduce the quenching process, improve phosphorescent yield and device characteristics, and obtain a compound with excellent stability and continuous current passage (paragraph 0086), as taught by Takiguchi.
Further, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound of Lee and Takiguchi in an OLED device with the claimed structure, as taught by Lee.
Such a modification produces a compound that meets the requirements of instant condition (1)(i) wherein x is 1, y is 2, and z is 0, A is a 6-membered heterocyclic (pyridine) ring, B is a 6-membered carbocyclic (benzene) ring, C is a 6-membered heterocyclic (pyridine) ring, D is a fused 6-membered carbocyclic and 5-membered heterocyclic (benzofuran) ring, Z1, Z3, Z4, Z5, Z7, and Z8 are a carbon atom, Z2 and Z6 are a nitrogen atom, K is a direct bond, one of RA is a C1 alkyl (methyl) group and one of RA is represented by Formula III, X1 through X5 are each a carbon atom, L is a direct bond, Q is a silicon atom, R1 through R3 are each a C1 alkyl (methyl) group, two RD are joined to form a fused benzene group, and RB and RC are not present.
With respect to claim 18, Lee and Takiguchi teach the OLED of claim 17, and Lee also teaches that the organic layer further comprises a host such as CBP (paragraph 0222), which comprises a carbazole moiety.
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It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use a host comprising a carbazole moiety as a host material for the compound of Lee and Takiguchi, as taught by Lee.
With respect to claim 20, Lee discloses a full color organic light-emitting device (a consumer product) comprising an anode, a cathode (paragraph 0181), and an organic layer between the anode and cathode, and the organic layer comprises (paragraph 0172) an organometallic compound for use in an organic electroluminescent device, such as compound 3 (paragraph 0167, page 27), which is pictured below.
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However, Lee does not teach nor fairly suggest that the compound also comprises a polycyclic fused-ring system comprising at least one 5-membered and at least one 6-membered ring.
In analogous art, Takiguchi also teaches organometallic compounds for use in an organic electroluminescent device.
Takiguchi teaches a bidentate ligand comprising two cyclic groups connected by a single bond wherein at least one cyclic group comprises a partial structure of formula (5) (paragraph 0084), which is pictured below.
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In this formula, Y is oxygen (paragraph 0043).
Takiguchi teaches that incorporating the aromatic group of formula (5) into a metal coordination compounds allows for control of the emissive wavelength (particularly to provide a long emission wavelength). Further, the presence of the aromatic group of formula (5) enhances the solubility of the metal coordination compound in an organic solvent, facilitating purification thereof by recrystallization or column chromatography (paragraph 0085). The aromatic group of formula (5) is also able to change the intermolecular interaction of the compound with the host material by suppressing thermal deactivation and formation of exciton associates. This reduces the quenching process and improves phosphorescent yield and device characteristics. For this reason, a metal coordination compound comprising a moiety of formula (5) exhibits excellent stability and continuous current passage (paragraph 0086).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate a moiety of formula (5) into the phenylpyridine ligand of Lee in order to allow for control of the emissive wavelength, enhance the solubility of the metal coordination compound in an organic solvent, facilitate purification thereof by recrystallization or column chromatography, change the intermolecular interaction of the compound with the host material by suppressing thermal deactivation and formation of exciton associate, reduce the quenching process, improve phosphorescent yield and device characteristics, and obtain a compound with excellent stability and continuous current passage (paragraph 0086), as taught by Takiguchi.
Further, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound of Lee and Takiguchi in an consumer OLED device, such as a full color device, with the claimed structure, as taught by Lee.
With respect to claim 21, Lee and Takiguchi teach the compound of claim 1, as discussed above.
Compound 3, pictured and discussed above, is derived from Lee Formula 2-2 (paragraph 0151), which is pictured below.
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Lee also teaches that R13 is CD3 (paragraph 0148) and R2 is CD3 (paragraph 0146).
Such a modification produces the compound found on the third row, first column of page 56 of the instant claims.
Lee includes each element claimed, with the only difference between the claimed invention and Lee being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which excellent electric characteristics and thermal stability which can be used to form an organic light-emitting device with low driving voltage, high efficiency, and high color purity (paragraph 0330), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 22, Lee and Takiguchi teach the compound of claim 1, and y is 2, D is a fused 6-membered carbocyclic and 5-membered heterocyclic (benzofuran) ring, Z1, Z3, Z4, Z5, Z7, and Z8 are a carbon atom, and Z2 and Z6 are a nitrogen atom, as discussed above.
With respect to claim 23, Lee and Takiguchi teach the compound of claim 1, as discussed above.
Compound 3, pictured and discussed above, is also derived from Lee Formula 1(2) (paragraph 0134), which is pictured below.
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Lee also teaches that R11 is CH3 (paragraph 0148).
Such a modification produces the compound that meets the requirements of the instant claim.
Lee includes each element claimed, with the only difference between the claimed invention and Lee being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which excellent electric characteristics and thermal stability which can be used to form an organic light-emitting device with low driving voltage, high efficiency, and high color purity (paragraph 0330), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Claim 24 is rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (US 2016/0141526 A1) and Takiguchi et al. (US 2003/0068535 A1) as applied above, and further in view of Park et al. (WO 2009/082043 A1).
With respect to claim 24, Lee and Takiguchi teach the compound of claim 1, as discussed above.
However, neither Lee nor Takiguchi teaches a moiety of Formula III wherein L is an organic linker.
In analogous art, Park teaches organometallic compound for use in an organic electroluminescent device comprising a bidentate ligand, wherein the pyridine cyclic group of the bidentate ligand is substituted by an organic linking group comprising a silyl group (paragraph 3 of page 2 and Chemical Formula 1 on page 3).
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Similar to Lee, Park teaches that the linking group at Ar1 may be a phenylene group (see Formula 2 on page 4). However, Park expands upon the work of Lee by giving examples of additional linking groups at Ar1 which include a fluorene group according to Formula 9 (page 4), which is pictured below.
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This linking group meets the requirements of the instant claim when ring E is a phenylene group and L is an organic moiety.
Park teaches that the iridium complexes disclosed have excellent solubility and can be used to form a film using a solution coating method. Further, when the compounds are used as a red phosphorescent dopant, the organic electroluminescent device comprising the compounds have excellent efficiency, color purity, and stability.
Lee teaches a compound of instant Formula I wherein L is a direct bond and ring E is a phenylene group. This compound differs from the compounds of the instant claim which comprise a phenylene group and an organic linker. However, Park teaches that both of phenylene linking groups and the combination of a phenylene linking group and an organic moiety were known in the art prior to the effective filing date of the claimed invention. It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to substitute the known element of a phenylene linking group with the known alternative of a phenylene linking group and organic moiety since the simple substitution would have yielded the predictable result an iridium compound with excellent solubility, and which can be used to form a film using a solution coating method to form an organic electroluminescent device with excellent efficiency, color purity, and stability, as taught by Park (see MPEP 2143).
Claim 25 is rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (US 2016/0141526 A1) and Takiguchi et al. (US 2003/0068535 A1) as applied above, and further in view of Tsai et al. (US 2017/0365800 A1).
With respect to claim 24, Lee and Takiguchi teach the compound of claim 1, as discussed above.
However, neither Lee nor Takiguchi teaches a compound requiring three different bidentate ligands.
In analogous art, Tsai teaches an iridium complex comprising three different bidentate ligands and their use in OLEDs to enhance the device efficiency and lifetime (abstract).
Tsai teaches that iridium complexes comprising three different bidentate ligands provide better device efficiency and lifetime when incorporated into OLED devices (paragraph 0054).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate a third, different bidentate ligand into the compound of Lee and Takiguchi in order to provide better device efficiency and lifetime when incorporated into an OLED device, as taught by Tsai.
Such a compound meets the requirements of the instant claim when x, y, and z are all 1.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Lee et al. (KR 2018/0020878A) – teaches preferential combination of a silyl group and dibenzofuran group in an organometallic ligand (paragraph 0216).
Xia et al. (US 2010/0244004 A1) – teaches a single dibenzofuran ligand.
Xia et al. (US 2014/0231755 A1) – teaches deuteration of ligand substituents.
Kim et al. (US 2015/0090974 A1) – see compound P-26 on page 17.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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/RACHEL SIMBANA/Examiner, Art Unit 1786
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