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 December 23, 2020.
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 Statement filed on
June 22, 2023 have been considered. A signed copy of the corresponding 1449 form has been included with this office action.
Specification
6. The disclosure is objected to because of the following informalities:
the structures provided in the list of compounds (A1-A106, B1-B160, C1-C150, D1-D155, and E1-E160) on pgs. 35-54 are small, blurry, and difficult to read.
7. Appropriate correction is required.
Claim Rejections - 35 USC § 112
8. 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.
9. Claims 1-12 and 15-22 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.
10. Claim 1 recites the limitation “… when a sum of a+b is 1 or more; or when Y is CRaRb or SiRaRb, at least one of Ra and Rb has a cyano group.” Given the use of the word “when” and the semi-colon, it is unclear whether the limitation is requiring: i) wherein at least one of Ra and Rb has a cyano group when a sum of a+b is 1 or more; or ii) wherein a sum of a+b is 1 or more; or wherein at least one of Ra and Rb has a cyano group when Y is CRaRb or SiRaRb.(and the sum of a+b is not necessarily 1 or more). For purposes of examination, the limitation will be interpreted as interpretation ii).
11. Claim 1 recites Chemical Formula 1 (shown below) and recites the limitation “…a and b are each an integer in a range from 0 to 2…”. It is unclear where the cyano groups (CN)a and (CN)b would be bonded to on the Y-containing ring of Chemical Formula 1 if a and/or b are integers greater than or equal to one given that all of the valencies on the Y-containing ring are satisfied by the substitution with R1 to R8. For the purposes of examination, the interpretation for a and/or b being integers greater than or equal to one is that the cyano groups (CN)a and/or (CN)b will replace the corresponding substituent R1 to R8 at the point of attachment to the Y-containing ring and thus the substituent R1 to R8 replaced with the cyano groups (CN)a and/or (CN)b will not be present.
PNG
media_image1.png
307
440
media_image1.png
Greyscale
12. Claims 2-12 and 15-22 are also rejected by virtue of their dependence upon claim 1.
Claim Rejections - 35 USC § 102
13. 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.
14. The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
15. Claims 1-7, 9-12, 15-18, and 20-22 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Huh et al. (provided by applicant in the IDS filed June 22, 2023: KR 20200033769 A – English machine translation obtained from WIPO, hereinafter “Huh”).
16. Per claim 1, Huh discloses compound 2-6 (Huh) (pg. 18, shown below) which reads on all of the limitations of Chemical Formula 1 wherein:
PNG
media_image2.png
279
543
media_image2.png
Greyscale
X1 to X3 are each independently nitrogen atoms; and
Ar1 and Ar2 are each independently C6 aryl groups; and
L1, L2, L4, and L5 are all single bonds; and
L3 is a C6 arylene group; and
A is a monocyclic hydrocarbon ring group containing one nitrogen atom; and
R1 and R3 to R8 are each independently hydrogen atoms; and
R2 is not present as it is replaced by a cyano group (CN)a since a is an integer equal to one; and
Y is CRaRb, and Ra and Rb are each independently C1 alkyl groups; and
the sum of a+b is equal to one.
17. Per claims 11-12 and 20-22, Huh discloses an organic electroluminescent device (see Table 1, Device Example 6) that reads on all of the limitations therein comprising:
an anode (ITO, pg. 22); and
a cathode (Al, pg. 22); and
one or more organic layers disposed between the anode and cathode (1st HTL, 2nd HTL, EML, ETL, pg. 22); and
compound 2-6 is included in at least one of the one or more organic layers (the ETL, in which compound 2-6 (Huh) is an ETL material).
18. Per claims 2 and 15, Huh discloses compound 2-6 (Huh) and an organic electroluminescent device comprising compound 2-6 (Huh) as an ETL material that reads on the limitation wherein A is selected as
PNG
media_image3.png
124
131
media_image3.png
Greyscale
.
19. Per claims 3 and 16, Huh discloses compound 2-6 (Huh) and an organic electroluminescent device comprising compound 2-6 (Huh) as an ETL material that reads on the limitation wherein
PNG
media_image4.png
160
190
media_image4.png
Greyscale
is selected as Chemical Formula A-5, and Ar1 and Ar2 are the same as defined previously.
20. Per claim 4, Huh discloses compound 2-6 (Huh) that reads on the limitation wherein Ar1 and Ar2 are each independently C6 aryl groups.
21. Per claims 5 and 17, Huh discloses compound 2-6 (Huh) and an organic electroluminescent device comprising compound 2-6 (Huh) as an ETL material that reads on the limitation wherein Ar1 and Ar2 are each independently
PNG
media_image5.png
102
126
media_image5.png
Greyscale
.
22. Per claim 6, Huh discloses compound 2-6 (Huh) that reads on all of the limitations wherein:
L1, L2, L4, and L5 are all single bonds; and
L3 is a linker selected as
PNG
media_image6.png
85
148
media_image6.png
Greyscale
.
23. Per claims 7 and 18, Huh discloses compound 2-6 (Huh) and an organic electroluminescent device comprising compound 2-6 (Huh) as an ETL material that reads on the limitations of Chemical Formula 6 wherein:
A, X1 to X3, L1 to L5, Ar1 and Ar2, R1 to R8, Ra and Rb, a and b are each the same as previously defined.
24. Per claims 9 and 20, Huh discloses compound 2-6 (Huh) and an organic electroluminescent device comprising compound 2-6 (Huh) as an ETL material that reads on the limitation wherein the Y-containing ring is selected as
PNG
media_image7.png
137
264
media_image7.png
Greyscale
25. Per claim 10, Huh discloses compound 2-6 (Huh) that reads on all of the limitations wherein:
R1 and R3 to R8 are each independently hydrogen atoms; and
R2 is not present as it is replaced by a cyano group (CN)a since a is an integer equal to one.
Claim Rejections - 35 USC § 103
26. 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.
27. 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.
28. 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.
29. 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.
30. Claims 8 and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Huh et al. (KR 20200033769 A – English machine translation obtained from WIPO, hereinafter “Huh”) as applied to claim 1 under 35 U.S.C. 102(a)(1) and (a)(2), as discussed above, and in view of Eum et al. (WO 2016105050 A1 – English machine translation obtained from WIPO, hereinafter “Eum”).
31. Regarding claims 8 and 19, the compound 2-6 (Huh) and the organic electroluminescent device comprising compound 2-6 (Huh) as an ETL material, as taught by Huh, fails to read on the limitations of Chemical Formulae 8-11 in that the monocyclic or polycyclic hydrocarbon ring group represented by B is not present.
32. Huh, however, does teach in Chemical Formula 2 (Huh) (see pg. 2) that L1 may be selected as a C6-C36 arylene group (pg. 8).
33. Eum teaches compounds represented by Chemical Formula 1 (Eum) (¶ [0029]) that are useful as ETL materials in organic electroluminescent devices (¶ [0061]) and that can be used to achieve excellent driving voltage, luminous efficiency, and lifespan (¶ [0061]).
34. Eum teaches that the substituents R1 and R2 on the fluorenyl moiety of Chemical Formula 1 (Eum) may be joined together to form an additional fused ring (¶ [0014], see structure below).
PNG
media_image8.png
295
621
media_image8.png
Greyscale
35. Eum specifically discloses compounds LE-07 and LE-10 (¶ [0083] and [0108]) shown below and teaches the use of both as lifespan improvement layers (see Table 5 – Examples 18 and 20), which function effectively as an ETL (see ¶ [0048]-[0060]).
PNG
media_image9.png
642
533
media_image9.png
Greyscale
36. Compounds LE-07 (Eum) and LE-10 (Eum) are identical in all respects except for compound LE-10 (Eum) possessing an additional benzo-moiety fused to the fluorenyl scaffold.
37. As demonstrated by the lifespan device data (in hours, T97) presented in Table 5, compound LE-10 (Eum) exhibits a significantly improved lifespan compared to compound LE-07 (Eum), which lacks the additional benzo-moiety fused to the fluorenyl scaffold.
38. 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 fuse an additional benzo-moiety on onto the fluorenyl scaffold of compound 2-6 (Huh) as shown in Eum’s compound LE-10, based on the teaching of Eum, based on the teaching of Eum. The motivation for doing so would have been to improve device lifetime, as taught by Eum (see lifespan data; Table 5 – Examples 18 and 20).
39. The compound 2-6 (Huh), as modified by Eum, is shown below.
PNG
media_image10.png
390
612
media_image10.png
Greyscale
40. Per claims 8 and 19, the compound 2-6 (Huh, Eum modification) and the organic electroluminescent device comprising compound 2-6 (Huh, Eum modification) as an ETL material reads on the all of the limitations of Chemical Formula 10 wherein:
B is a monocyclic hydrocarbon ring group; and
A, X1 to X3, L1 to L5, Ar1 and Ar2, R1 to R8, Y, Ra and Rb, a and b are each the same as previously defined.
Conclusion
41. The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. The references of Yoon et al. (KR-20200032020-A, English machine translation obtained from WIPO; see compounds on pgs. 14-24) and Arai et al. (JP-2018115125-A, English machine translation obtained from Global Dossier; see Chemical Formula 1 ¶ [0011] and compounds A-1 to A-108 ¶ [0039]-[0050]) disclose compounds that are relevant with respect to Chemical Formula 1 of the instant application.
42. 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.
43. 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.
44. 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.
45. 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.
/B.J.C./Examiner, Art Unit 1786
/BRAELYN R WATSON/Primary Examiner, Art Unit 1786
Prosecution Insights