DETAILED ACTION
Notice of Pre-AIA or AIA Status
1. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
2. Acknowledgment is made of applicant's claim for foreign priority based on
applications filed in Korea on March 5, 2021.
3. Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C.
119(a)-(d) prior to declaration of an interference, a certified English translation of the
foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and
41.202(e).
4. Failure to provide a certified translation may result in no benefit being accorded
for the non-English application.
Information Disclosure Statement
5. The references provided in the Information Disclosure Statements filed on September 1, 2023 and August 4, 2025 have been considered. Signed copies of the corresponding 1449 forms have been included with this office action.
Specification
6. The disclosure is objected to because of the following informalities:
the chemical structures provided in the list of compounds 1-180 beginning on pg. 41 of the instant specification are small, blurry, and difficult to read; and
numerous depictions of chemical formulae and structures throughout the specification are of low resolution and difficult to read (see formulae on pgs. 19 and 26 of the instant specification as examples).
7. Appropriate correction is required.
Claim Objections
8. Claim 4 is objected to because of the following informalities:
the chemical structures provided in the list of compounds 1-180 are small, blurry, and difficult to read.
9. Claims 6-9 are objected to because of the following informalities:
claim 5 recites “…one or more organic material layers…” while claims 6-9, which depend upon claim 5, recite “…wherein the organic material layer…”
for the purposes of clarity, it is suggested that claims 6-9 instead recite “… wherein the one or more organic material layers…”
10. Appropriate correction is required.
Claim Rejections - 35 USC § 103
11. 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.
12. 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.
13. 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.
14. 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.
15. Claims 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over DE 202013012401 U1 (hereinafter “App. ‘401”) in view of Sun et al. (CN 106083861 A; hereinafter “Sun”).
16. Regarding claim 1-4, App. ‘401 teaches compounds represented by Formula [1] (App. ‘401) (¶ [0016]-[0027]) that are useful as hole injection, hole transport, and/or exciton blocking materials in organic light emitting devices (¶ [0014]).
17. App. ‘401 teaches that compounds represented by Formula [1] have advantageous characteristics of at least:
low sublimation temperature, high thermal and oxidative stability, and high glass transition temperatures which facilitates facile organic light emitting device fabrication (¶ [0123]); and
high hole mobility (¶ [0123]); and
affording high efficiency, low operating voltage, and long service lifetimes when used as a hole injection and/or hole transport material (¶ [0123]).
18. App. ‘401 discloses the following compound shown below represented by Formula [1] (App. ‘401 – see Formel 118: ¶ [0074] and compound 1-15: ¶ [0123], which are identical).
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469
816
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19. Compound 1-15 of App. ‘401 reads on the limitations of Chemical Formulae 1 and 2 of claim 1 wherein:
Ar1 and Ar2 are each independently unsubstituted C6 aryl groups; and
R1-R4 and R6-R8 are each independently hydrogen atoms; and
R5 is represented by Chemical Formula 2; and
L is a direct bond and l is an integer equal to one; and
La and Lb are direct bonds, and a and b are integers equal to one; and
Ra and Rb are each independently unsubstituted C12 aryl groups.
20. Compound 1-15 of App. ‘401 fails to read on the limitation of Chemical Formula 1 wherein there is an alkynyl linker between Ar2 and position C9 of the fluorene group.
21. However, App. ‘401 does teach that each R1 of Formula [1] (App. ‘401) can be independently selected as:
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308
535
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C6-C30 aryl groups (¶ [0016]); and
C2-C20 alkynyl groups which can be substituted with C6-C30 aryl groups (¶ [0016]).
22. Sun teaches organic light emitting materials and organic light emitting devices comprising the light emitting materials of Sun (pg. 1, Technical Field).
23. Sun teaches at least the following benefits of introducing an alkynyl linker within organic compounds wherein:
the energy gap between the HOMO and LUMO levels of the compound comprising an alkynyl linker becomes smaller [pg. 1, Background of the Invention, (i)]; and
hole and electron mobility are significantly increased because the introduction of alkynyl linker enables significant reduction of undesired hole and electron recombination [pg. 1, Background of the Invention, (iii)]; and
hole and electron mobility of the compound comprising the alkynyl linker are also improved by an increase in the length of the conjugated system [pg. 1, Background of the Invention, (iv)].
24. 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 introduce an alkynyl linker in compound 1-15 of App. ‘401, based on the teaching of Sun. The motivation for doing so would have been to minimize the energy gap between the HOMO and LUMO, and improve hole and electron mobility, as taught by Sun [pg. 1, Background of the Invention, (i), (iii), (iv)].
25. Additionally, 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 one of the C6 aryl groups of compound 1-15 (App. ‘401, see circled area below)
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430
748
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with a C6 aryl-substituted alkynyl group, because it would have been choosing a specific location in compound 1-15 at which to include the alkynyl linker as a known group for R1 in Formula [1] (App. ‘401), which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the hole injection and/or transport material in the hole injection and/or transport layers of the organic light emitting device of App. ‘401 and possessing the benefits taught by App. ‘401. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula [1] (App. ‘401) having the benefits taught by App. ‘401 (low sublimation temperature, high thermal and oxidative stability, high glass transition temperatures, and high hole mobility, ¶ [0123]) in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
26. The modified compound 1-15 (App. ‘401, Sun) resulting from the alkynyl introduction discussed above is shown below.
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360
401
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27. Per claim 1, the modified compound 1-15 (App. ‘401, Sun) reads on all of the limitations of Chemical Formulae 1 and 2 wherein:
Ar1, Ar2, R1-R8, L, La, Lb, l, a, b, Ra, and Rb are all the same as previously defined.
28. Per claim 2, the modified compound 1-15 (App. ‘401, Sun) reads on all of the limitations of Chemical Formula 2-1 wherein:
L, La, Lb, l, a, and b are the same as previously defined; and
R11 and R12 are each independently unsubstituted C12 aryl groups.
29. Per claim 3, Chemical 2-2 is not required to be present, as per claim 2, and thus the limitation is met.
30. Per claim 4, the modified compound 1-15 (App. ‘401, Sun) reads on the limitation wherein it is identical to compound 136.
31. Regarding claims 5-10, App. ‘401 teaches an organic light emitting device (¶ [0168]-[0175]) comprising:
a first electrode (ITO, ¶ [0169]); and
a second electrode (Al, ¶ [0169]); and
one or more organic material layers provided between the first electrode and the second electrode (HIL, HTL, EBL, EML, ETL ¶ [0169]); and
one or more layers of the organic material layers comprise the heterocyclic compound of any one of claim 1 (¶ [0172], [0174]-[0175]).
32. App. ‘401 specifically teaches compound 1-15 (App. ‘401) in the EBL of an organic light emitting device (Table 1, Example E9).
33. While App. ‘401 teaches the compound 1-15 (App. ‘401) in the EBL of an organic light emitting device and generally teaches uses of the compounds disclosed therein in an organic light emitting device of claim 5, App. ‘401 does not specifically teach the modified compound 1-15 (App. ‘401, Sun) in an organic light emitting device.
34. At the time the invention was effectively filed, it would have been obvious to
one of ordinary skill in the art to have modified the organic light emitting device of App. ‘401 by substituting compound 1-15 (App. ‘401) with modified compound 1-15 (App. ‘401, Sun) in the EBL of App. ‘401, based on the teaching of App. ‘401 (low sublimation temperature, high thermal and oxidative stability, high glass transition temperatures, and high hole mobility, ¶ [0123]). The modification would have been a combination of prior art elements according to known methods to yield predictable results. See MPEP 2143(I)(A).
35. Per claims 5, 7, and 10, the modified organic light emitting device of App. ‘401, comprising modified compound 1-15 (App. ‘401, Sun) in the EBL reads on all of the limitations as previously described.
36. Per claim 6 and 9, the modified organic light emitting device of App. ‘401, comprising modified compound 1-15 (App. ‘401, Sun) in the EBL reads on the limitations of claim 6 wherein the EBL has the same function as an HTL (to facilitate the effective transport of holes), and claim 9 wherein the EBL has the same function as an HIL (to facilitate the effective transport of holes).
37. Per claim 8, the modified organic light emitting device of App. ‘401, comprising modified compound 1-15 (App. ‘401, Sun) in the EBL reads on the limitation in that the light emitting auxiliary layer, as per the definition provided on pg. 52 of the instant specification, has the function of facilitating hole transfer, hole injection, and electron blocking, which is the same as the EBL.
Conclusion
38. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Brandon J. Cooper whose telephone number is (571)272-0005. The examiner can normally be reached Monday - Friday 8:30 AM - 5:00 PM.
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40. 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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/B.J.C./Examiner, Art Unit 1786
/BRAELYN R WATSON/Primary Examiner, Art Unit 1786
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