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 .
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 (i.e., changing from AIA to pre-AIA ) 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.
Election/Restrictions
Applicant’s election without traverse of species (A) and formula A(1) in the reply filed on 02/21/2025 is acknowledged.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on each of 06/27/2025 and 07/14/2025 has been considered by the examiner.
Response to Amendment
Claims 1, 7, 9, and 15 are amended and claims 2-6, 8, and 10-13 cancelled due to the applicant's amendment.
The applicant's amendment of 06/11/2025 has been entered.
Claims 1, 7, 9, and 14-19 are pending.
The rejection of claims 1, 7, 9, and 14-19 under 35 U.S.C. 103 as being unpatentable over Kosuge et al. US-20150295188-A1 in view of Zhang et al. US-20200099000-A1 as set forth in the previous Office action is overcome due to the applicant's amendment.
However, as outlined below, new grounds of rejection have been made further teachings of Kosuge.
Response to Arguments
The applicant’s arguments on pages 17-22 of the reply dated 06/11/2025 with respect to the rejection of claims under 35 U.S.C. 103 as being unpatentable over Kosuge et al. US-20150295188-A1 in view of Zhang et al. US-20200099000-A1 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument – The applicant argues on pages 17-22 that the prior art does not provide any reason(s) to modify the compound of Kosuge/Zhang to derive the exact subject matter of claim 1. More specifically, the applicant argues that the features of improved quantum yield and luminous efficiency as taught by Kosuge are stated for the entirety of general formula of Kosuge and therefore nothing in the prior art of record would have motivated the persona having ordinary skill in the art to select the claimed species/subgenus of claim 1.
Examiner's response – The invention of the prior art is not limited to or defined by only those embodiments disclosed in the examples. A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill the art, including nonpreferred embodiments. See MPEP § 2123. While Kosuge does to expressly recite a compound as claimed, as described in detail in the rejection of record, it would have been obvious to arrive at the claimed compound in view of the teachings of Kosuge and Zhang and in each case the substitutions would have been one preferred element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as the guest in the light-emitting layer of the organic light-emitting element of Kosuge and possessing the properties/benefits taught by Kosuge (And Zhang). Further, one of ordinary skill in the art would have been motivated to produce additional compounds represented the formula [1] having the benefits as described above taught by Kosuge in order to pursue the known options within their technical grasp with a reasonable expectation of success.
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, 7, 9, and 14-19 are rejected under 35 U.S.C. 103 as being unpatentable over Kosuge et al. US-20150295188-A1 (hereinafter "Kosuge") in view of Zhang et al. US-20200099000-A1 (hereinafter "Zhang").
It is noted that Kosuge is cited on the IDS of 08/10/2023.
Regarding claims 1, 7, 9, 14, and 16-18, Kosuge teaches an organic light-emitting element comprising in order anode/hole-transporting layer/electron blocking layer/light-emitting layer/hole-blocking layer/electron-transporting layer/cathode (¶ [0047]) wherein the light-emitting layer comprises an iridium complex represented by the general formula [1]
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and the heterocycle-containing compound represented by the general formula [5] (¶ [0052], ¶ [0039]). Kosuge teaches the organic light-emitting element has extremely high luminous efficiency (¶ [0119]), emits red light (¶ [0119], ¶ [0134]), and has long lifetime (¶ [0134]).
Kosuge discloses specific examples of the iridium complex represented by the general formula [1] including Ir-504
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(¶ [0136], page 25). In the above iridium complex, the bidentate ligand X of the general formula [1] of Kosuge is
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.
Kosuge does not specifically disclose an organic light- emitting element comprising an iridium complex represented by the general formula [1] as discussed above wherein the benzo[f]lisoquinoline is additionally substituted with a group that does not comprise a fluoro group (-F) and is not hydrogen. However, Kosuge teaches that the iridium complex represented by the general formula [1] is particularly preferably an iridium complex represented by the following general formula [20]
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(¶ [0084]), wherein Q1 to Q9 each represent hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, or a cyano group (¶ [0085]) and teaches specific examples of an alkyl group include a methyl group and a tert-butyl group (¶ [0063]). Further, Kosuge teaches iridium complexes represented by the general formula [20] wherein Q1 and/or Q2 are a methyl group including Ir-113 (¶ [0136], page 14) and wherein Q1 and/or Q2 are a t-butyl group including Ir-112 and Ir-217 (¶ [0136], page 13 and page 17).
Therefore, given the general formula and teachings of Kosuge, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to further substitute at least the position corresponding to Q1 and/or Q2 in the general formula [20] of Kosuge in the modified iridium complex of Kosuge, as discussed above, with one of a non-fluorine halogen atom, an alkyl group (a methyl group and a tert-butyl group), an alkoxy group, or a cyano group, because Kosuge teaches the variables may suitably be selected as such and exemplifies compounds wherein Q1 and/or Q2 is substituted. The substitution would have been one preferred element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as the guest in the light-emitting layer of the organic light-emitting element of Kosuge and possessing the benefits taught by Kosuge. See MPEP § 2143.1.(B).
Further, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to specifically select one of a non-fluorine halogen atom, an alkyl group, an alkoxy group, or a cyano group because Kosuge exemplifies compounds wherein Q1 and/or Q2 is substituted and it would have been choosing from the list of positions and the list substituents taught for Q1 and Q-2 in the formula [20] of Kosuge, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the emitter in the light-emitting layer of the organic light-emitting element of Kosuge and possessing the benefits as described above taught by Kosuge. One of ordinary skill in the art would have been motivated to produce additional compounds represented the formula [1] having the benefits as described above taught by Kosuge in order to pursue the known options within their technical grasp with a reasonable expectation of success. See MPEP § 2143.1.(E).
Kosuge does not specifically disclose a compound as discussed above wherein the positions corresponding to R9 and R11 in claimed Formula A(1) are each independently a C1-C20 alkyl group, a C3-C10 cycloalkyl group, or a C2-C10 heterocycloalkyl group, each unsubstituted or substituted with deuterium, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, or any combination thereof. However, Kosuge teaches that ring A may be a benzene ring and may have a substituent (¶ [0020]) and teaches exemplary compounds wherein ring A is a benzene ring substituted with two methyl groups such as Ir-106
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(¶ [0136], page 13).
Therefore, given the general formula and teachings of Kosuge, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the unsubstituted benzene ring in the position corresponding to ring A in the general formula [1] of Kosuge and CY2 in the claimed Formula 1 in the modified compound Ir-504 with a benzene ring substituted with two methyl groups as shown in Ir-106, because Kosuge teaches the variable may suitably be selected as such and teaches exemplary compounds with that group. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful in the light emitting layer of the device of Kosuge and possess the benefits of improved sublimation purification, quantum yield, and luminous efficiency, as taught by Kosuge. See MPEP 2143.I.(B).
Kosuge does not specifically disclose a compound as discussed above wherein the bidentate ligand X of the general formula [1] of Kosuge is a group corresponding to the claimed
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. For example, the compound Ir-504 shown above differs from the claimed compound in that the bidentate ligand X of the general formula [1] of Kosuge is not a group corresponding to the claimed
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. However, Kosuge teaches X represents a bidentate ligand in the general formula [1] of Kosuge and may specifically be represented by a general formula [2] to [4] (¶ [0071]) which include both
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and
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(¶ [0071]). Further, Kosuge teaches that the acac-based ligand (diketone-based bidentate ligand) has a small molecular weight such that the compound comprising the ligand can be easily subjected to sublimation purification and the compounds comprising the ligands of the general formula [1] and the acac-based ligand have an extremely high emission quantum yield such that the incorporation of any such complex as a guest into the light-emitting layer provides an organic light-emitting element having high luminous efficiency (¶ [0138]).
Zhang teaches an electroluminescent device comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a metal complex comprising an acac-based ligand La represented by Formula 1
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(¶ [0017]). Zhang teaches the metal complex comprising the ancillary ligand La can be used as an emitter in the emissive layer of an organic electroluminescent device and that the ancillary ligand La can alter the sublimation properties of luminescent materials, improve quantum efficiency and device performance (¶ [0024]). Zhang discloses examples of the ancillary ligand La (¶ [0083]) including La5
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(page 7), La20
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(¶ [0083], page 9), La26
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(¶ [0083], page 10) and La28
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(¶ [0083], page 10) and teaches exemplary devices comprising compounds comprising La26 (¶ [0141]–[0144]).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the X bidentate ligand in the modified complex Ir-504 of Kosuge with an acac-based ligand and to select the acac-based ligand as one of the ligands of Zhang. The motivation for doing so would have been to improve sublimation purification, quantum yield, and luminous efficiency, as taught by Kosuge, and to improve quantum efficiency and device performance, as taught by Zhang.
Further, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to specifically select the ancillary ligand as La5
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, La20
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, La26
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, or La28
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, because it would have been choosing from the list of specifically disclosed ancillary ligands of Formula 1 of Zhang, which would have been a choice from a finite number of identified, predictable solutions of an ancillary ligand La for use in a metal complex in the emissive layer of an organic electroluminescent device and possessing the benefits taught by Zhang. One of ordinary skill in the art would have been motivated to produce additional compounds comprising ancillary ligands represented by Formula 1 of Zhang having the benefits taught by Zhang in order to pursue the known options within their technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The organic light emitting device comprising modified compound of Kosuge in view of Zhang meets claims 1, 7, 9, 14, and 16-18.
Regarding claim 15, Kosuge in view of Zhang teaches the device comprising the modified compound as discussed above with respect to claim 1.
Kosuge in view of Zhang does not specifically disclose a compound as listed in claim 15. The modified compound wherein Q2 is a t-butyl group the ancillary ligand is La5 of Zhang as discussed above differs from the claimed compound
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in that the -CF3 group is substituted at the position corresponding to the claimed R5 instead of the position corresponding to the claimed R7. However, Kosuge teaches that the position corresponding to the claimed R6 may be a trifluoromethyl group, among others (¶ [0061]).
Therefore, given the general formula and teachings of Kosuge, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of the compound discussed above wherein the -CF3 group is substituted at the position corresponding to the claimed R6. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by the general formula of Kosuge in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful in the light emitting layer of the device of Kosuge in view of Zhang and possess the properties of improved sublimation purification, quantum yield, and luminous efficiency, as taught by Kosuge, and improved quantum efficiency and device performance, as taught by Zhang. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP § 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP § 2144.09 II.
The further modified compound has the structure
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.
Regarding claim 19, Kosuge in view of Zhang discloses the device as described above with respect to claim 18.
Kosuge in view of Zhang is silent to wherein the modified organometallic compound emits red light.
In the instant specification in Table 4, it is shown that Examples 1-3 comprising compounds 4, 1, and 6, respectively emit red light. The modified compound of Kosuge in view of Zhang is substantially similar in structure to compounds 4, 1, and 6. Additionally, as noted above, Kosuge teaches the organic light-emitting element emits red light (¶ [0119], ¶ [0134]).
Since Kosuge in view of Zhang teaches a substantially similar structure as that disclosed by the Applicant which emits red light, the property of red light emission is considered to be inherent, absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP § 2112.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure:
Kishino et al. US-20150303386-A1 and Kamatani et al. US-20150333279-A1 also teach metal complex Ir-504
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(page 24 and page 32, respectively); and
Kosuge et al. US-20150295188-A1, cited on the IDS of 06/18/2024, Kishino et al. US-20150303386-A1, and Kamatani et al. US-20150333279-A1 teach metal complex Ir-209
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(page 16, page 14).
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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Elizabeth M. Dahlburg whose telephone number is 571-272-6424. The examiner can normally be reached Monday through Thursday, 9 a.m. to 4 p.m. ET, and alternate Fridays.
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/ELIZABETH M. DAHLBURG/Primary Examiner, Art Unit 1786