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 .
Summary of Claims
Claim 7 is amended due to Applicant’s amendment dated 23 February 2025. Claims 1-10 are pending.
Response to Amendments
The rejection of claim 7 under 35 U.S.C. 112(d) as being of improper dependent form is overcome due to the Applicant’s amendment dated 23 February 2026. The rejection is overcome.
The rejection of claims 1 and 2 under 35 U.S.C. 103 as being unpatentable over Park et al. (KR20200078254) is not overcome due to the Applicant’s argument dated 23 February 2026. The rejection is maintained.
The rejection of claims 3-10 under 35 U.S.C. 103 as being unpatentable over Park et al. (KR20200078254) in view of Lee et al. (Chem. Commun. 2016, 52, 10032), and in view of Lee et al. (US20180123049) is not overcome due to the Applicant’s argument dated 23 February 2026. The rejection is maintained.
Response to Arguments
Applicant’s arguments on pages 13-18 of the reply dated 23 February 2026 with respect to the rejection of claims 1-10 as set forth in the previous Office Action have been fully considered, but they are not persuasive.
Applicant’s Argument – Applicant argues that compounds of the claimed embodiments exhibit unexpected and desirable results with respect to at least one property including driving voltage, efficiency, and life-span over the cited prior art. Applicant points to a comparison of Examples 1-7 and Comparative Examples 1-5 as shown in Table 1 for support (instant Specification, pg 55 ¶ [00216]). Applicant points to (1) Example 1 with compound 1 compared to Comparative Example 4 with Host 3 and (2) Example 2 with compound 2 compared to Comparative Example 5 with Host 4 for support. As Host 3 of Comparative Example 4 is identical to the cited compound of Park, Applicant argues the claimed embodiments would not have been obvious over Park.
Examiner’s Response – Overcoming a rejection based on unexpected results requires at least the combination of three different elements: (i) the results must fairly compare with the closest prior art in an affidavit or declaration under 37 CFR 1.132, (ii) the claims must be commensurate in scope, and (iii) the results must truly be unexpected. MPEP 716.02. Additionally, the burden rests with Applicant to establish the results are unexpected and significant. MPEP 716.02(b).
As shown in page 52-54 of the instant specification, the structures of Comparative Examples 1 to 5 and inventive Examples 1 to 7 are the same comprising Ir (PPy)3 as dopant and a host compound as demonstrated by Table 1 (¶ [00196] – [00202]).
Unexpected Results
The properties of driving voltage, efficiency, and life-span pertain to the device in which the compound is applied and not directly to the compound itself. An appropriate comparison would require a comparison of properties directly attributable to the compound itself.
While there are improvements in driving voltage, efficiency, and life-span between (1) Example 1 and Comparative Example 4, (2) Example 2 and Comparative Example 5, and (3) Examples 1-7 and Comparative Example 2, it is not clear whether these performance improvements are truly unexpected.
Example 1 displays a 6% decrease in driving voltage, 12% increase in efficiency and a 133% increase in life-span when compared to Comparative Example 4, that corresponds to Compound 1 of Park. Example 1 displays a 1-3% decrease in driving voltage, a 7-9% increase in efficiency, and a 23-50% increase in life-span when compared to either Comparative Example 2 or 3, that corresponds to Compound 2 of Park. Note that Compound 2 of Park features two carbazoles connected to the core carbazole at the 1- and 8-positions. Compound 2 in Example 2 of Park shares similarity with Host 1 and Host 2 of the instant specification because all compounds feature two carbazoles connected to the core carbazole wherein Host 1 is connected at positions 2- and 7- and Host 2 is connected at positions 1- and 3-.
Given the device property values of Examples 1-7, the instant devices show a driving voltage variability of 4%, an efficiency variability of 13%, and a life-span variability of 60%. Similarly, as shown in Table 1 of the instant specification, Comparative Examples 1-5 show a driving voltage variability of 20%, an efficiency variability of 24%, and a life-span variability of 2125%. These variabilities illustrate the degree to which one of ordinary skill in the art could expect device properties to differ simply by altering the host compound therein. Given that the degree of improvement shown by Examples 1-7 significantly overlaps with the degree of variability shown by (1) Examples 1-7 and (2) Comparative Examples 1-5, it is unclear whether the improvement is unexpected.
Additionally, one of ordinary skill in the art would recognize that devices comprising compounds having different structures would not result in identical properties. Accordingly, one of ordinary skill would expect some degree of difference in driving voltage, efficiency, and life-span between devices of Examples 1-7 and Comparative Example 1-5.
Thus, in light of the variability between instant devices and the variability between comparative devices, and given that one of ordinary skill in the art would expect some difference between devices comprising compounds having different structure, it is unclear whether the degree of improvement shown by the data in the instant specification is truly unexpected.
Commensurate in Scope
The example devices of the instant specification uses one particular dopant material, Ir(PPy)3, is not required by the claims. Therefore, examples with other dopant materials would offer a clearer comparison in the life-span improvement and whether it is attributable to the claimed compound.
The definitions of L1, L2, L3, Ar1, and Ar2 in the Chemical Formula 1 of instant claim 1 are much broader in scope than the small number of specific Examples shown in the Tables. Therefore, it is not clear that similar results would be present if there were another falling within the scope of the formula such as a heterocyclic group.
While Example 1 displays a 133% improvement in life-span over Comparative Example 4, Example 5 displays a 122% improvement in life-span over Comparative Example 4. That is, given that Example 1 and 5 are both claimed embodiments, the same degree of improvement is not shown across the full scope of what is being claimed.
Additionally, Example 5 displays a 17% improvement in life-span over Comparative Example 3, which corresponds to the Compound 2 of Park. While some of the compounds display a large improvement in lifespan compared to the Compound 1 of Park, the same may not apply to compounds corresponding to other compounds of Park such as Compound 2 of Park. These other comparisons within the scope of the claims exhibit much smaller increases. Accordingly, it cannot be said that unexpected results are demonstrated across the full scope of what is being claimed with respect to the properties of driving voltage, efficiency, and life-span.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-2 are rejected under 35 U.S.C. 103 as being unpatentable over Park et al. (KR20200078254A). Note that a machine-generated translation is provided with this office action.
Regarding claim 1, Park teaches an organic light-emitting device having a first electrode, a second electrode, and one or more layers of organic matter between the first and second electrodes. An aromatic, heterocyclic compound Formula 3-4 is contained in the organic matter layer where Formula 3-4 is the following:
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Park teaches: R1-R2 being aryl or heteroaryl, X1-X3 each independently being N or CR with at least one being N, and Y1-Y2 being hydrogen, aryl, arylamine, or heteroaryl groups (claim 10). In preferred embodiments, Y1 and Y2 are specifically “hydrogen, deuterium, phenyl, diphenylamine, or…carbazole” (description of Formula 3-1 to 3-4). Park also discloses the efficiency and luminance properties for specific Compound 2 following generic structure Formula 1 where Y1 and Y2 are carbazole, R1 and R2 are phenyl, and X1-X3 are N forming a triazine (claim 11, Table 2):
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342
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It would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select carbazole as Y1 and Y2 for Formula 3-4 of Park because it would have been a choice from a finite number of identified, predictable solutions of a compound useful as the organic dopant material in the emissive layer of the electroluminescent device and possessing the benefits taught by Park. The motivation for doing so would have been to optimize for both luminance and efficiency as taught by Park. See MPEP 2143.I.(E). The burden of proof is now shifted to applicants to show otherwise unexpected results.
Regarding claim 2, Park teaches the compound as claimed in the instant claim 1 wherein L3 is a single bond.
Claims 3-10 are rejected under 35 U.S.C. 103 as being unpatentable over Park et al. (KR20200078254A) in view of Lee et al. (Chem. Commun. 2016 52, 10032) and further in view Lee et al. (US20180123049).
Regarding claim 3, Park teaches the compound as claimed in instant claim 1 featuring a 1,5-dicarbazoylcarbazole linked to a triazine where L3 is a single bond. Park fails to teach L3 being a substituted or unsubstituted ortho-phenylene group.
Lee (2016) teaches in the analogous art of light-emitting organic materials that there is a “low QE issue of the linker free TADF emitters” for the basic backbone structure containing diphenyl triazine and a carbazole (Pg 10032, Column 2). A phenyl linker inserted between the triazine and carbazole moieties manages the HOMO/LUMO separation to achieve higher efficiency (QE).
The skilled artisan would have been motivated to combine Park and Lee (2016) by inserting a phenylene linker between the substituted triazine and 1,5-dicarbazoylcarbazole to achieve a higher QE compound.
The combination of Park and Lee (2016) fails to teach the ortho-substitution pattern for the moieties on the phenylene linker compared to the meta- and para- positions.
Lee (‘049) teaches in the analogous art of organic light-emitting materials the phenylene linker with an ortho-substitution between the electron-donating carbazole and the electron-withdrawing triazine demonstrated in Chemical Formula 7 (Page 39, Claim 3).
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Lee (‘049) also teaches the ortho-substituted phenylene linker having the smallest energy difference between the singlet state and triplet state compared to the other meta- and para- forms (Table 1, para 27 and 190). A smaller singlet-triplet splitting translates to a higher efficiency material due to an easier Reverse Intersystem Crossing (RISC) via thermally activated delayed fluorescence.
One of ordinary skill in the art would have expected success at the time of invention in formulating a compound of instant claim 3 through combining the previous combination of Park and Lee (2016) with Lee (‘049). One of ordinary skill in the art would have selected the ortho-phenylene over the meta- and para-substitutions in order to minimize the singlet-triplet splitting, thereby improving the efficiency of the aryl-triazine and 1,5-dicarbazoylcarbazole system.
Regarding instant claim 4, Park teaches phenyl, biphenyl, naphthyl, or terphenyl as preferred aryl groups of R1 and R2 of Formula 3-4 (Park claim 3, claim 7).
Regarding instant claim 5, Park teaches a single bond for L1 and L2 between the triazine and aryl groups (Park claim 3, claim 11).
Regarding instant claim 6, Park teaches Formula 3-4 where R1 and R2 are each independently a phenyl, biphenyl, naphthyl, terphenyl or 9-carbazole (Park claim 3, claim 11).
Regarding instant claim 7, the preferred embodiment of Park Formula 3-4 may be aryl groups such as phenyl at R1 and R2, carbazole groups at Y1 and Y2 (Park claim 10, claim 11).
Regarding instant claim 8-10, Park teaches an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers between the electrodes including compounds with Formula 3-4 (Park claim 12). The organic light-emitting device comprises the compound as a dopant material in the light-emitting layer, as well as electronic devices containing organic light-emitting elements (Park claim 14, claim 16).
Conclusion
THIS ACTION IS MADE FINAL. 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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/L.Q.N./ Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786
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