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 07/24/2026 was filed after the mailing date of the instant application on 01/12/2023. 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 07/24/2026, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the objection to claims 1 and 4 are withdrawn by the Office.
Claims 1-20 were originally filed.
Claims 5 and 11-12 are canceled.
Claims 1, 4, 8-9 and 13 are instantly amended.
Claims 1-4, 6-10, and 13-20 are pending in the application.
Response to Arguments
Applicant's arguments have been fully considered but they are not persuasive. Applicant’s amendments do not overcome the prior art because the prior art still reads on the claimed invention.
Specifically, there is no teaching nor suggestion in Ma or Yeager that the 5-membered ring which is condensed to the dibenzoheterole moiety cannot or should not be an oxazole group which cannot or should not comprise a phenyl substituent.
A reinterpretation of the prior art is given below to explain how the prior art still reads on the claimed invention.
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 1-4, 6-10, and 13-20 are rejected under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2013/0181190 A1) and further in view of Yeager et al. (US 2021/0288269 A1).
With respect to claims 1-4, Ma discloses a heteroleptic iridium complex containing a phenyl pyridine ligand and another ligand containing a dibenzofuran linked to an imidazole or benzimidazole fragment (abstract).
Ma gives an example of such a compound in Compound 6-O (page 8 and paragraph 0059 which defines X), which is pictured below.
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This compound is derived from Formula I (paragraph 0060) which is pictured below.
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However, while Ma teaches that R3 can represent disubstitution and adjacent R3 can be linked (paragraph 0046), Ma does not teach nor fairly suggest that two R3 are joined to form a 5-membered heterocyclic group.
In analogous art, Yeager teaches heteroleptic iridium complexes containing benzo-fused ligands (abstract) wherein at least two adjacent substituents on the non-coordinated benzene ring of the dibenzofuran moiety are joined to form a condensed, 5-membered heterocyclic group (paragraph 0013) represented by Formula II, which is pictured below.
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In Formula II, Z1 is an oxygen atom (paragraph 0073), Z2 is a nitrogen atom (paragraph 0015), and RB is a phenyl group (paragraph 0016, see also the compounds on page 98).
Yeager teaches that compounds with these features demonstrate blue-shifted emission and allow for fine tuning of emission color (paragraph 0212).
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 join two adjacent R3 in the dibenzofuran moiety of Compound 6-O of Ma to form the condensed, 5-membered ring of Formula II of Yeager in order to blue-shift the emission color of the organometallic complex as well as allow for fine tuning of emission color, as taught by Yeager.
While Yeager teaches all of the instantly claimed bonding patterns between the 5-membered ring and dibenzoheterole moiety (see pages 19-20 of Yeager), for the sake of this correspondence, the structure of instant Formula 21-1 is being used.
Such a modification produces a compound of instant Formula 1 when M1 is iridium, Ln1 is represented by Formula 1A, Ln2 is represented by Formula 21-1, n1 is 2, and n2 is 1. In Formula 1A, X1 is a nitrogen atom and CY1 is a C5 heterocyclic (pyridine) group, X2 is a carbon atom and CY2 is a 6-membered carbocyclic (benzene) group, b10 is 4, b20 is 4, and R10 and R20 are both hydrogen atoms. In Formula 21-1, X31 is C(R31), X32 is C(R32), R31 and R32 are joined to form a benzimidazole moiety, a1 is 1 and L1 is a 1,5-diisopropyl substituted C6 carbocyclic (phenylene) group, b5 is 1 and R5 is a C6 aryl (phenyl) group, Y1 is an oxygen atom, R1-R2 and R41-R42 are hydrogen atoms, X41 is a nitrogen atom, X42 is an oxygen atom, R45 is a phenyl group, and X33-X36 are each CH (see for example ligand LA1401-45 on pages 19 and 32 for support).
With respect to claim 6, Ma and Yeager teach the compound of claim 1, and the pyridine ring of CY1 is instant 1-1, as pictured above.
With respect to claim 7, Ma and Yeager teach the compound of claim 1, and the benzene group of CY2 is represented by instant 2-1, as pictured above.
With respect to claims 8 and 9, Ma and Yeager teach the compound of claim 1, and R1 and R2 are hydrogen atoms, R3 and R4 are not present, R5 is a phenyl group (10-12, claim 9), R10 and R20 are hydrogen atoms, R31 and R32 are joined to form a benzene ring, R33 to R36 are hydrogen atoms, R41 and R42 are hydrogen atoms, R43 and R44 are not present, R45 is a phenyl group (10-12, claim 9), and R46 and R47 are not present, as pictured and discussed above.
With respect to claim 10, Ma and Yeager teach the compound of claim 1, as discussed above.
Ma also teaches that in Formula I, R1 which is analogous to instant R10 can be deuterium (paragraph 0060, line 9).
Ma includes each element claimed, with the only difference between the claimed invention and Ma being a lack of the aforementioned deuterium atom 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 substituents to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound which, when incorporated into OLED devices, can result in devices with improved efficiency and lifetimes (paragraph 0048), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 13, Ma and Yeager teach the compound of claim 1, and the compound is represented by instant formula 31-7 when X11-X24 are CH. All other variables are as defined above.
With respect to claim 14, Ma and Yeager teach the compound of claim 1, and the compound is instant compound 5.
With respect to claims 15-17 and 19, Ma and Yeager teach the compound of claim 1, and Ma also teaches an organic light emitting device comprising an anode, a cathode, and an organic layer between the electrodes comprising the compound of Formula I (paragraph 0060). The organic layer comprises a hole transport region comprising a hole transport layer, an emissive layer, and an electron transporting region comprising an electron transporting layer (paragraph 0037 and Figure 1), and Ma teaches use of the compounds of the invention as a dopant in combination with a host in the emitting layer, and the amount of the dopant is 7, 10, or 13 wt % (Paragraph 0067 and Table 1).
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 Ma and Yeager as a dopant in the emitting layer of an organic light-emitting device with the claimed device structure, as taught by Ma.
With respect to claim 18, Ma and Yeager teach the device of claim 16, as discussed above.
Examiner is interpreting the compound of Ma and Yeager to produce a wavelength within the claimed range, which can meet the requirements of the instant claim through its use as a preferred embodiment of the claimed invention, as given through the use of identical compound 5 on page 41 of the instant specification. Products of identical chemical composition cannot have mutually exclusive properties, and it has been held that when the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present (See MPEP 2112.01(II)), and the compound of Ma and Yeager reads on the claims.
Ma teaches the compounds of the invention demonstrate an emissive wavelength within the claimed range (see Table 2 on page 14) and Yeager teaches that the condensed 5-membered heterocyclic ring results in a blue-shift in emission wavelength. Neither explicitly states what the emission wavelength of such a combination would be. However, this is considered to be a property of the composition. Support for this presumption comes from the use of like materials and like processes when the compound of Ma and Yeager is used as an emissive dopant in the organic layer of an electroluminescent device, which would result in the claimed property described in the instant claims. Therefore, the claims are considered to be obvious over Ma and Yeager, and the burden shifts to applicant to show that there is an unobvious difference between the claimed composition and the composition in the prior art. See MPEP 2112 (V). In addition, the presently claimed properties are considered to be present once the work of Ma and Yeager was first provided. See MPEP 2112.01 (II).
With respect to claim 20, Ma and Yeager teach the device of claim 15, and Ma also teaches that optoelectronic devices are suitable for us in apparatuses such as organic phototransistors, organic photovoltaic cells, and organic photodetectors (paragraph 0003).
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 device of Ma and Yeager in an apparatus such as an organic phototransistor, as taught by Ma.
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.
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached at 571-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/RACHEL SIMBANA/Primary Examiner, Art Unit 1786
