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 .
Status of Claims
This office action is in response to the amendment received on 14 April 2026. Claims 1, 7-8, and 15 are amended. Claims 1-20 are pending.
Response to Amendment
Acknowledgment is made of Applicant’s certified English language translation of the priority document of Korean Application No. 10-2021-0143081 to perfect the foreign priority claim.
The objection to the specification as set forth in the previous Office Action is overcome due to the Applicant’s amendment to the specification dated 14 April 2026. The objection is withdrawn.
The rejection of claims 1-20 under 35 U.S.C. 103 as being unpatentable over Yi et al. (US2021/0288268 A1, hereinafter “Yi”) is overcome due to the Applicant’s affidavit dated 14 April 2026. Applicant’s statement of common ownership and certified translation of the Korean priority documents has rendered Yi ineligible as prior art. The rejection is withdrawn.
The rejection of claims 1-20 under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 20200287143 A1, hereinafter “Kim”) in view of Ordonez et al. (ES 2642114 A1, hereinafter “Ordonez”) is overcome due to the Applicant’s amendment dated 14 April 2026. The rejection is withdrawn.
Response to Arguments
Applicant’s argument with respect to claims 1-20 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.
Claims 1-7 and 9-20 are rejected under 35 U.S.C. 103 as being unpatentable over Hwang et al. (US 2016/0155962 A1, hereinafter "Hwang") in view of Ordonez et al. (ES 2642114 A1, hereinafter “Ordonez”). Note that a machine-generated English translation is relied upon and provided with this office action.
Regarding claims 1-15, Hwang teaches, in the field of organic light emitting devices, an iridium complex represented by general formula “Formula 2A-3” where an aryl-pyridine ligand may be substituted with a silyl group at the pyridine (claim 10). Hwang discloses specific examples of the iridium complex represented by Formula 2A-3 including the compound 146, shown below, wherein X1 of the general formula is O and Y3 to Y8 is C (pg 64).
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Compound 146 of Hwang is a compound of Formula 2A-3 where R1 to R3 is methyl, forming a trimethyl silyl or “TMS” group. Hwang teaches that the addition of the TMS group to various positions of the pyridine ligand leads to an improvement in the efficiency, lifespan, and a reduction in voltage when compared to examples without the TMS group such as compound A (Pg 145-146, Table 2).
Hwang does not specifically disclose an iridium complex that meets the claimed Formula 1. Compound 146 shown above differs from the claimed compound in that the phenylpyridine ligand of Compound 146 is not a group corresponding to the claimed Formula 1 ligand represented by the instant Formula 1B. However, Hwang does not particularly limit the ancillary ligand to be phenyl-pyridine; instead, Hwang defines L2 in Hwang’s general Formula 1 as being selected from a monovalent, divalent, trivalent and a tetravalent organic ligand (claim 1, pg 146)
Ordonez teaches in the pertinent art of photodynamic therapy and electroluminescent devices an Ir(III) complex with the General Formula of [Ir(C^N)2(N^O)] where (C^N) is a cyclometalated ligand and (N^O) is an arylazole ligand that may be represented by the General Formula shown below (Description and Technical Sector). Ordonez teaches in the General Formula that X can be N-H or N-Me and Y can be O (claim 2). Ordonez discloses specific examples of the iridium complex represented by the General Formula [Ir(C^N)2(N^O)] where the cyclometalated ligand is a phenylpyridine and the arylazole ligand is a hydroxyphenyl benzimidazole shown below, referred hereinafter as Compound of Claim 22 (claim 22).
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Ordonez teaches that the (N^O) ligands, such as the one found in Compound of Claim 22, display excellent phosphorescence intensity and quantum yields while improving emission times and the efficiency of absorbed energy. (Description, pg 3).
22. 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 phenylpyridine ligand of Compound 146, as taught by Hwang, and to select the (N^O) ligand as of Compound 22, as taught by Ordonez. The motivation for doing so would have been to improve efficiency, lifetime, and a reduction in voltage, as taught by Hwang, and to improve emission times and the efficiency of absorbed energy, as taught by Ordonez.
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 ligand where X is N-Me because it would have been choosing from the list of specifically disclosed identities for X, which would have been a choice from a finite number of identified, predictable solutions of an arylazole ligand (N^O) for use in a metal complex in the emissive layer of an organic electroluminescent device and possessing the benefits taught by Ordonez. One of ordinary skill in the art would have been motivated to produce additional compounds comprising arylazole (N^O) ligands represented by General Formula of Ordonez having the benefits taught by Ordonez in order to pursue the known options within their technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E). The modified compound of Hwang in view of Ordonez is shown below.
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The above Modified Compound of Hwang in view of Ordonez is a compound of the claimed instant Formula 1 wherein:
M1 is Ir;
Ln1 is Formula 1A;
Ln2 is Formula 1B;
n1 is 2 and n2 is 1;
ring CY3 is a 5-membered N-containing heterocylic group condensed with a C6 carbocyclic group (benzimidazole);
ring CY4 is a 6-membered carbocyclic group (phenylene);
Y1 is O;
Y2 is O;
At least one of R1, R2, R11-R14, R30 or R40 (namely R12) is -Si(Q1)(Q2)(Q3) where Q1, Q2, and Q3 are Me (Si(Me)3 or “TMS”);
R2, R11, R13, R14, R21 to R26, R30 and R40 are each independently hydrogen
Ln2 is represented by Formula 1B-2;
X33 is N(R33);
N(R33) is methyl; and
CY3 is represented by Formulae 3-5.
The Modified Compound of Kim in view of Ordonez teaches compound 33 of instant claim 15 as discussed above.
The organic light emitting device comprising modified compound of Kim in view of Ordonez meets claims 1-7 and 9-15.
Regarding claims 16-20, Hwang teaches an organic light emitting device comprising: an ITO electrode, m-MTDATA hole injection layer, a-NPD hole injection layer, Compound 1 and CBP emission layer, BAlq hole blocking layer, Alq3 electron transport layer, LiF electron injection layer, and Al second electrode in that order wherein Compound 1, a compound of Hwang’s Formula 1, and CBP serve as a host and dopant in the emission layer (pg 144, ¶ [0440] – [0443]). Hwang further teaches that the organometallic compound 1 is 10% of the emission layer, wherein the CBP host is greater than an amount of the organometallic compound in the emission layer (pg 144, ¶ [0443]). Hwang teaches that the organic light-emitting element, containing Compound 1 and CBP, may be manufactured in an electronic organic light-emitting device displaying excellent driving voltage, efficiency, power, color purity, and lifespan (¶ [0446] – [0449]). Hwang teaches the above; however, Hwang does not teach a specific device containing the Modified Compound of Hwang and Ordonez.
Hwang teaches an anode, a cathode, and an organic layer and the compound 1 is in the organic layer as discussed above. It would have been obvious to use the modified compound of Hwang and Ordonez in the organic layer with the device structure of anode, hole transport, emission layer, electron transport, and cathode as Hwang demonstrates this device structure was known prior to the effective filing date of the claimed invention. The resulting device reads on instant claims 15-20.
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Hwang et al. (US 2016/0155962 A1, hereinafter "Hwang") and Ordonez et al. (ES 2642114 A1, hereinafter “Ordonez”) as applied to claims 1-7 and 9-20 described above, in view of Choi et al. (US 2018/0273563 A1, hereinafter "Choi").
Hwang and Ordonez teach the Modified Device containing the Modified Compound of Hwang and Ordonez that reads on instant claims 1-7 and 9-20 as described above. Hwang and Ordonez is silent on the organometallic complex wherein at least one of R11 and R21 to R24 of the general formula of instant claim 1 is -Ge(Q1)(Q2)(Q3).
In the relevant art of organic light-emitting devices, Choi teaches organometallic, iridium compounds 17 and 18, shown below, wherein a substituted pyridine ligand features a trimethyl silyl “TMS” group, and a corresponding complex wherein the TMS group is replaced with a trimethyl germyl “TMG” group (pg 22-23).
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The compounds 17 of Choi is similar to the compound 146 of Hwang in that both are iridium (III) organometallic complexes that are neutral and feature an aryl-pyridine ligand wherein the aryl group is dibenzofuran and the pyridine group is substituted and features a TMS group. The compound 17 of Choi differs from the compound of Hwang in that the pyridine group features substitution wherein the aromatic group is fused to the pyridine to form a condensed ring system. Therefore, Choi teaches that TMG is functionally equivalent to a TMS group for an iridium complex that features a ligand system containing a dibenzofuran-pyridine.
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 TMS group, with a TMG group, of the Modified Compound of Hwang and Ordonez in the light-emitting device of Hwang and Ordonez, based on the teachings of Choi. The motivation for doing so would be because Choi teaches that TMG and TMS are functionally equivalent substituents for iridium complexes that feature a ligand system containing a dibenzofuran-pyridine.
The resulting Modified Compound of Hwang, Ordonez, and Choi reads on instant claim 8.
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
/JENNA N CHANDHOK/Primary Examiner, Art Unit 1789
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