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 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.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on July 10, 2026 has been entered.
Status of Claims
This action is in reply to the communication filed on July 10, 2026.
Claim 9 has been amended is hereby entered.
Claims 12 – 21 have been added.
Claims 1 – 8, 10 and 11 have been canceled.
Claims 9, and 12 – 21 are currently pending and have been examined.
Terminal Disclaimer
The terminal disclaimer filed on July 9, 2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of U.S. Patent 12,686,661 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Response to Amendments
Applicant’s amendments to the claims, filed July 10, 2026, caused the withdrawal of the rejection of claims 1 – 11 under 35 U.S.C. 103 as being unpatentable over Yang as set forth in the office action filed April 10, 2026.
Response to Arguments
Applicant's arguments filed July 10, 2026 have been fully considered but they are not persuasive.
Applicant argues that Yang does not teach or suggest any effect associated with including deuterium on the pendant carbazole group and that the instant Application determined that the addition of at least four deuterium substituents on the carbazole group improves the device lifetime when the compound is provided in a light emitting layer. Applicant points to the comparison of Example 1 and Example 13 to Comparative Example 3 as evidence of this property. Examiner respectfully disagrees. As it relates to the data shown in the Examples cited by Applicant, Examiner notes that while Compound 1 and Compound 13 show improved lifespan as compared to the undeuterated compound CE3, no comparison or results have been shown as to the effect of deuterium on the core structure in other locations, such as compound 1-41 in Yang. Therefore, it is not possible to determine whether the effects on the device lifespan can be ascribed to the inclusion of deuterium generally or are only present for the particularly claimed location of the deuterium substitutions. Additionally, the Example compounds show 5 and 6 deuterium substitutions, respectively. No compound has been shown with 4 deuterium substitutions, the minimum required by the claim, nor has a compound with 1 – 3 deuterium substitutions been shown, as evidence that a minimum number of deuterium substitutions as claimed is required for the improved properties.
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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
Determining the scope and contents of the prior art.
Ascertaining the differences between the prior art and the claims at issue.
Resolving the level of ordinary skill in the pertinent art.
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 9 and 12 – 19 are rejected under 35 U.S.C. 103 as being unpatentable over (WO2021091259A1, using US20220396568A1 as the official English language translation) in view of Tsuji (Tsuji et al. “The Hydrogen/Deuterium Isotope Effect of the Host Material on the Lifetime of Organic Light-Emitting Diodes.” Chem Comm. (2014) 50: 14870.).
As per claims 9 and 12 – 17, Yang teaches:
An organic light emitting device comprising a first electrode, a second electrode that is provided opposite to the first electrode, and one or more organic material layers that are provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers comprise the compound of claim 1 ([0019]: “In addition, one embodiment of embodiment of the present application provides an organic light emitting device comprising a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers comprise the heterocyclic compound represented by Chemical Formula 1.”)
Wherein one or more of the organic material layers is a light emitting layer that comprises a compound of Chemical Formula 1
PNG
media_image1.png
266
406
media_image1.png
Greyscale
(Yang teaches heterocyclic compounds of Chemical Formula 1
PNG
media_image2.png
208
332
media_image2.png
Greyscale
([0010]). A particular compound taught by Yang is compound 1-41
PNG
media_image3.png
314
348
media_image3.png
Greyscale
([0129]). Compound 1-41 does not teach that the carbazole group contains at least four deuterium atoms as currently claimed. However, Yang teaches that since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium and that even though a substituent is not shown in the compound structure, hydrogen and deuterium may be mixed as long as deuterium is not explicitly excluded ([0041 – 0043]). Therefore, the compound 1-41 of Yang can be interpreted as containing any number of deuterium substitutions, including the particularly claimed pattern of deuterium substitution claimed. Furthermore, Tsuji teaches that the hydrogen/deuterium exchange of a C-H bond in an OLED host material increases the lifetime of the device (Page 14871, Right Column, Last Paragraph). Therefore, it would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to provide the deuterium atoms in the claimed locations and arrive at the claimed compound, because Yang teaches that even though a substituent is not explicitly shown, it may still be deuterium ([0041 – 0043]) and Tsuji teaches that the predictable benefits of substituting a hydrogen atom for a deuterium atom include increased device lifetime. When modified in this way, the modified compound reads on the claimed Formula wherein each X is independently N; Y is O; L1 is a direct bond; L2 is a direct bond; Ar1 and Ar2 are both an unsubstituted C6 aryl, namely a phenyl as required by claim 16; R1 is a substituted C6 aryl, namely a phenyl as required by claim 17, wherein R1 is substituted with deuterium. & [0026]: “Particularly, the compound can be used as a light emitting material of the organic light emitting device. For example, the compound can be used alone as a light emitting material, or two of the compounds can be used together as a light emitting material, and can be used as a host material of a light emitting layer.”)
Wherein the light emitting layer also comprises Compound YGH-1
PNG
media_image4.png
262
178
media_image4.png
Greyscale
([0020]: “In addition, one embodiment of the present application provides a composition for an organic material layer of an organic light emitting device, the composition comprising the heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by the following Chemical Formula 2.”
PNG
media_image5.png
184
302
media_image5.png
Greyscale
A specific compound within the scope of Chemical Formula 2 taught by Yang is compound 3-4
PNG
media_image6.png
292
314
media_image6.png
Greyscale
, which is the same as claimed compound YGH-1.)
Yang includes each element claimed, with the only difference between the claimed invention and Yang being a lack of the aforementioned combination being explicitly stated. 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 combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable results of improved efficiency, lower driving voltage and/or improved lifetime ([0021]), absent a showing of unexpected results commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E). Additionally, a person having ordinary skill in the art would have been further motivated because Tsuji teaches that the predictably benefits of substituting a hydrogen atom for a deuterium atom include increased device lifetime.
Yang teaches an anode, a cathode, and an organic layer and that the compound is in the organic layer as discussed above. It would have been obvious to use the compound in the organic layer with the device structure of Yang as Yang demonstrates this device structure was known prior to the effective filing date of the claimed invention.
As per claim 18, the only difference between another compound taught by Yang, namely compound 1-1 of Yang
PNG
media_image7.png
300
354
media_image7.png
Greyscale
and claimed compound
PNG
media_image8.png
138
176
media_image8.png
Greyscale
is the deuterium substitution on the carbazole ring. However, Yang teaches that since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium and that even though a substituent is not shown in the compound structure, hydrogen and deuterium may be mixed as long as deuterium is not explicitly excluded ([0041 – 0043]). Therefore, the compound 1-1 of Yang can be interpreted as containing any number of deuterium substitutions, including the particularly claimed pattern of deuterium substitution claimed. It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to provide the deuterium atoms in the claimed locations and arrive at the claimed compound, because Yang teaches that even though a substituent is not explicitly shown, it may still be deuterium ([0041 – 0043]).
Yang includes each element claimed, with the only difference between the claimed invention and Yang being a lack of the aforementioned combination being explicitly stated. 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 combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable results of improved efficiency, lower driving voltage and/or improved lifetime ([0021]), absent a showing of unexpected results commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
As per claim 19, Yang teaches:
Wherein the light emitting layer comprises a dopant that is an iridium complex ([0145]: “As another example, the organic material layer comprising the heterocyclic compound comprises the heterocyclic compound represented by Chemical Formula 1 as a host, and an iridium-based dopant may be used therewith.”)
Allowable Subject Matter
Claims 20 and 21 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: As per claims 20 and 21, Yang teaches Ir(ppy)3 and Ir(piq)2(acac) dopants, but Yang does not teach, suggest or motivate a person of ordinary skill in the art to use the specific Ir-based dopant claimed. Furthermore, Yang teaches the dopants present in an amount of either 3% or 7% by weight. Yang does not teach, suggest, or motivate a person of ordinary skill in the art to provide the compounds in the particular ratio claimed.
Conclusion
All claims are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JENNA N CHANDHOK whose telephone number is (571)272-5780. The examiner can normally be reached on Monday through Friday from 6:30 - 3:30.
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, Marla McConnell can be reached on 571-270-7692. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/JENNA N CHANDHOK/Primary Examiner, Art Unit 1789
Prosecution Insights