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 .
Priority
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in parent Application No. KR10-2021-0066142, filed on 05/24/2021.
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 11/08/2023, 11/08/2023, 08/26/2025, 12/03/2025, and 07/15/2026 were filed after the mailing date of the instant application on 11/08/2023. The submissions are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Response to Amendment
In the preliminary amendments dated 11/08/2023, the claims were amended.
These amendments are hereby entered.
Claims 1-11 were originally filed.
Claim 6 is instantly amended.
Claims 1-11 are pending in the application.
Specification
The disclosure is objected to because of the following informalities:
In the reaction diagram of <Preparation Example 11> on page 107 of the instant specification, “suzuki” should be capitalized.
On pages 138 and 143 of the instant specification, the structure of 2-TNATA is illegible due to low resolution. Please correct this.
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Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-11 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
With respect to independent claim 1, the claim requires that the compound comprises 1-100 % deuterium content. It is unclear if this is relative to molecular weight, mole weight, hydrogen content, etc.
In continuing examination, percent deuterium content is being interpreted as
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Claim Rejections - 35 USC § 103
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.
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 1-6 and 8-11 are rejected under 35 U.S.C. 103 as being unpatentable over Uno et al. (US 2022/0416174 A1, herein after referred to as Uno 2022) and further in view of Uno et al. (US 2019/0165285 A1, herein after referred to as Uno 2019).
With respect to claim 1, Uno 2022 discloses compound A38 (page 15), which is pictured below.
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This compound is derived from Formula 1 (paragraph 0006), which is pictured below.
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In this formula, Uno 2022 teaches that A1-A10 may each be independently selected as deuterium or a C6 aryl group (paragraph 0009), and one of A1-A10 has a structure of Formula 2-1, which is pictured below.
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In Formula 2-1, Uno 2022 is non-limiting with respect to the bonding position of the naphthyl group.
When a positional isomer of compound A38 is formed and modified to comprise the taught deuterium atoms, it produces the compound below.
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Uno 2022 includes each element claimed, with the only difference between the claimed invention and Uno 2022 being a lack of the aforementioned deuterium atoms 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 polycyclic compound which has a core structure including a benzonaphthofuran combined with an amine group which supports a decreased driving voltage, increased lifespan, and increased efficiency in an organic electroluminescence device by improving hole transport capacity such that the recombination of holes and electrons in the emission layer is improved (paragraph 0343), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Such a compound meets the requirements of instant Chemical Formula 1 when R1 to R8 are deuterium atoms, A has a structure of Chemical Formula 1-1, and B has the structure of Chemical Formula 1-2. In Chemical Formula 1-1, m is 0 and L is not present, r and s are 1 and L1 and L2 are each a C6 arylene (phenylene) group, Ar1 is a C6 aryl (phenyl) group and Ar2 is a C10 (naphthyl) group. In Chemical Formula 1-2, p is 1 and L3 is a C6 arylene (phenylene) group and q is 1 and Ar3 is a C6 aryl (phenyl) group. The compound is ~22% deuterated.
However, Uno 2022 does not teach nor fairly suggest the instantly required bonding pattern.
In analogous art, Uno 2019 teaches an amine compound comprising an aryl-substituted dibenzoheterole moiety (abstract). Uno 2019 teaches that important chemical properties, such as emission efficiency and emission life, can be optimized by changing the bonding pattern between the dibenzoheterole and the aryl substituent, and by changing the bonding pattern between the dibenzoheterole and the amine core (see paragraphs 0189-0200 for an in-depth discussion).
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 determine which locations on the benzonaphthofuran moiety to place the aryl substituent and amine bonds in order to produce the best emission efficiency and emission life of an organic electroluminescence device comprising the compound, as taught by Uno 2019. Further, absent a showing of unexpected results, it would have been within the technical grasp of a person of ordinary skill to synthesize a compound with any possible bonding pattern, including the pattern claimed, between aryl substituent, benzonaphthofuran, and amine core in the compound of Uno 2022 in order to obtain the maximum possible efficiency of emission and lifetime. (See MPEP 2144.05 (II)).
With respect to claim 2, Uno 2022 and Uno 2019 teach the compound of claim 1, and Chemical Formula 1 is represented by Chemical Formula 3, as pictured above.
With respect to claims 3 and 4, Uno 2022 and Uno 2019 teach the compound of claim 1, and the benzonaphthol furan moiety (Structural Formula A) is deuterated for a total percentage deuteration of ~22 %, as discussed above.
With respect to claim 5, Uno 2022 and Uno 2019 teach the compound of claim 1, and Chemical Formula 1 is represented by compound 74, as pictured above.
With respect to claims 6 and 8-11, Uno 2022 and Uno 2019 teach the compound of claim 1, and Uno 2022 also teaches an organic light emitting device comprising a first electrode (an anode), a second electrode (a cathode), an organic material layer between the electrodes comprising a plurality of organic layer such as a hole transport region, an emission layer, and an electron transport region, and the emission layer, the hole transport region (hole injection layer, hole transport layer, paragraph 0052, lines 3-5), the electron transport region (hole blocking layer (paragraph 0159), electron injection layer, electron transport layer, paragraph 0052, lines 5-7), and/or the capping layer comprises the compound (paragraph 0051).
Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Uno et al. (US 2022/0416174 A1, herein after referred to as Uno 2022) and Uno et al. (US 2019/0165285 A1, herein after referred to as Uno 2019), as applied above, and further in view of Lee et al. (US 2015/0364694 A1).
With respect to claim 7, Uno 2022 and Uno 2019 teach the device of claim 6, as discussed above.
Uno 2022 also teaches that the hole transport region may comprise a plurality of hole transport layers (paragraph 0055) and that the polycyclic compound may be present anywhere in the hole transport region (paragraph 0057). However, neither Uno 2022 nor Uno 2019 teach nor fairly suggest that the compound is in an emitting auxiliary layer.
In analogous art, Lee teaches organic compounds for use in an organic optoelectronic device (paragraph 0001).
Lee teaches that an organic light emitting diode may comprise an emission auxiliary layer and that the emission auxiliary layer may be a part of the hole transport region and may be a hole transport layer for improving efficiency and stability of an organic light emitting diode (paragraph 0006).
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 Uno 2022 and Uno 2019 in an emission auxiliary layer as the compound is taught in a hole transport layer and Lee teaches that an emission auxiliary layer is any hole transport layer.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Lee et al. (US 2022/0199911 A1) – teaches relevant benzonaphthofuran derivatives
Pan et al. (WO 2018/095383 A1, translation provided) – teaches that compounds have different properties when different moieties are deuterated (paragraph 0076).
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..
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
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
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