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 .
DETAILED ACTION
Response to Arguments
Applicants arguments and amendments, filed on 3/31/26, have been fully considered but they do not confer patentability on all of the instantly filed claims. Applicants have filed a terminal disclaimer which overcomes the double patenting rejection from the previous Office action. Applicants have amended independent claims 1 and 20 to recite that the phosphorescent dopant comprises a structure as shown in each of claims 1 and 20. All of the 8 ligands recited in claims 1 and 20 share the structural feature that the phosphorescent dopant comprises at least one ligand comprising a pyrimidine ring. Applicants have further amended claim 20 to recite that the energy of the HOMO of the hole blocking layer is at least 0.1 eV lower than the energy of the HOMO of the phosphorescent dopant. The claims have also been amended to overcome the objection to claim 5 and the 112(b) and 112(d) rejections of claims 5-9 and 17 and the 112(d) rejection of claims 15, 16, and 18.
The previously relied upon prior art rejection to Yang et al. (J. Organomet. Chem. 2006, 691, 2767-2773) has been withdrawn due to Applicants amendments. Applicants instantly filed claims includes a new proviso which states that if the phosphorescent dopant comprises the structure of
PNG
media_image1.png
144
144
media_image1.png
Greyscale
then at least one of RA or RB is not hydrogen or deuterium. The complex (4-pqz)2Ir(acac) as taught by Yang et al. only satisfies the above ligand where all RA and RB are hydrogen atoms. The complex (4-pqz)2Ir(acac) is the only complex disclosed by Yang et al. which comprises a pyrimidine moiety. Yang et al. does not provide any teaching or suggestion to modify the complexes described therein.
The previously relied upon prior art rejection to Nagai et al. (J. Mater. Chem. C 2017, 5, 527-530) has also been withdrawn due to Applicants amendments. The complex disclosed by Nagai et al. does not comprise a pyrimidine ring, which is a required structural feature of the instantly filed claims. The ligand disclosed by Nagai et al. comprises a pyrazine ring. Further search has led to new prior art rejections which are described below.
While Applicants have amended the independent claims, the addition of a new objection of Applicants figures and the fact that independent claim 20 was not subject to any prior art rejections in the previous Office action, but is rejected as shown below, this Office action is non-final.
Terminal Disclaimer
The terminal disclaimer filed on 3/31/26 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of US Pat. No. 11,515,482 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Drawings
The drawings are objected to under 37 CFR 1.84(a)(l) because figures 4 through 7 are illegible. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in response to this Office action. Any new drawing sheet must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” in accordance with 37 CFR 1.121(d)(1). Also see MPEP 608.02 for the general reference for the standards of drawings.
Claim Rejections - 35 USC § 102
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.
Claims 1, 2, 4, and 10-12 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Du et al. (Inorg. Chem. 2010, 49, 8713-8723 and the supporting information) as evidenced by two technical data sheets from Ossila.
Du et al. teaches the complex 4a which has the structure shown in Scheme 2 where the two NC ligands have the structure
PNG
media_image2.png
90
112
media_image2.png
Greyscale
. This complex comprises a ligand
PNG
media_image3.png
144
144
media_image3.png
Greyscale
where RB is equal to F and all RA is equal to hydrogen which satisfies the first proviso of independent claim 1. The HOMO energy level of this compound is taught in the supporting information to be -5.1 eV (Table S1 in the supporting information of Du et al.), which satisfies the HOMO energy level requirements as recited in claim 1. The emission spectra of a solution of complex 4a in methylene chloride has a maximum emission wavelength of 628 nm as shown in Table 2 and Figure 6 which satisfies the emission maximum requirements of claims 1 and 2. One having ordinary skill in the art would not expect a dilute solution of 4a in methylene chloride to have a significantly different emission profile compared to a doped (0.5 wt%) film in PMMA. Du et al. further teaches OLED fabrication where compound 4a is employed in an OLED device comprising an anode, a hole injection layer, a hole transport layer, an emission layer comprising a host and compound 4a as a phosphorescent dopant, an electron blocking layer (TCTA and TBPI), an electron transporting layer, and a cathode (page 8722, right column). The HOMO energy level of TCTA is -5.7 eV and the HOMO energy level of TBPi is -6.2 eV as evidenced by technical data sheets from Ossila. The HOMO energy level difference between 4a and TCTA is 0.6 eV which satisfies both claims 1 and 4 and the HOMO energy level difference between 4a and TBPi is 1.1 eV which satisfies both claims 1 and 4. Therefore, the device example taught by Du et al. anticipates all of the structural and device limitations of claims 1, 2, and 4.
Claims 10-12: Complex 4a as shown above comprises a metal-carbon bond, where the metal is Ir, and where the complex comprises a pyrimidine chemical moiety, thereby anticipating claims 10-12.
Claims 1, 3, 4, 10-16, and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Boudreault et al. (US 2015/0236277) as evidenced by a datasheet from Ossila.
Claims 1, 3, and 4: Boudreault et al. teaches organic electroluminescent materials and devices. The devices are comprised of an anode, a hole transport region, an emission layer, an electron transport region comprising a hole blocking layer which is located between the emission layer and the election transport layer, and a cathode. The emission layer is comprised of a host material and a phosphorescent iridium dopant which in many embodiments, including the device example, is an iridium dopant of the formula (L1)2(L3) where L1 is a ligand which comprises the structure
PNG
media_image4.png
144
142
media_image4.png
Greyscale
where at least one of RA and RB is not hydrogen or deuterium. Preferred ligands are taught in paragraph 0100 which includes compounds 81 (which is employed in the device example) and compound 87. Compounds 81 and 87 are also taught in Applicants specification as being suitable compounds according to the invention. The device which comprises compound 81 as the phosphorescent emitter is shown in Table 3 of Boudreault et al. as having a maximum emission wavelength of 668 nm, which is well above the “greater than or equal to 600 nm” as recited in claim 1 and above 610 nm as recited in claim 2. A person having ordinary skill in the art would expect that a 0.5 wt% film in PMMA comprising the complexes above would satisfy the emission wavelength requirements of claim 1 at least because compounds 81 (and 87) are explicitly taught as being suitable for Applicants invention. As such, it can be rationally supposed that at least compounds 81 and 87 would satisfy Applicants claimed emission peak maximum wavelength when employed in a doped PMMA film. Additionally, because compounds 81 and 87 are identical to some of Applicants preferred iridium complexes, it can also be rationally supposed that the HOMO energy level would be lower than or equal to -5.1 eV as recited in claim 1. Because the USPTO does not have a testing facility, the burden shifts to Applicants to show that this position is lacking by submitting evidence to the contrary. The exemplified device which employs compound 81 as the phosphorescent dopant also includes the complex BAlq as the material for the hole blocking layer (10 nm thickness). BAlq is taught in the Ossila data sheet as having a HOMO energy level of -5.9 eV. In order to satisfy claim 1, compound 81 as taught by Boudreault would need to have a HOMO energy level of between -5.1 eV and -5.7 eV, or between -5.2 eV and -5.7 eV to satisfy claim 3, or between -5.1 eV and -5.6 eV to satisfy claim 4. Applicants hole blocking materials as taught in Table 3 of the instantly filed specification to have a HOMO energy level of -5.64 eV, -5.70 eV, and -5.90 eV. Since BAlq is taught as having a deep HOMO energy level of -5.90 eV (which is the deepest HOMO level material exemplified by Applicants), there is a preponderance of evidence that the device example taught by Boudreault et al. which employs a phosphorescent dopant which is identical to one of Applicants preferred phosphorescent dopants and further teaches a hole blocking layer which matches the HOMO energy level of hole blocking material HBL3 in Applicants specification. For the reasons above, the device example taught by Boudreault et al. would be expected to satisfy Applicants device limitations of claims 1, 3, and 4.
Claims 10-12: Iridium complex 81 as taught by Boudreault et al. is an iridium complex comprising an iridium-carbon bond and a pyrimidine chemical moiety, thereby anticipating claims 10-12.
Claims 13-16: Iridium complex 81 of Boudreault et al. has the chemical structure
PNG
media_image5.png
112
170
media_image5.png
Greyscale
(page 105). This complex has the formula Ir(L1)2(L3), where L1 satisfies the second to last structure recited in claim 13 and L3 satisfies the first structure recited in claim 13 and the structure recited in claim 14. The formula Ir(L1)2(L3) satisfies claim 15 and 16 with L3 satisfying the ligand recited in claim 16.
Claim 20: The rejection of claim 1 above is wholly incorporated into the rejection of claim 20. Boudreault et al. teaches that the devices taught therein may be employed in a variety of consumer products (paragraph 0047). As such, the preparation of a consumer product comprising the OLED of claim 1 is at once envisaged, thereby anticipating claim 20.
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.
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.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Du et al. (Inorg. Chem. 2010, 49, 8713-8723).
The rejection of claim 1 as described above is wholly incorporated into the rejection of claim 20. Du et al. teaches an OLED which satisfies all of the limitations of claim 20 as described in claim 1 above. While Du et al. does not explicitly teach preparing a consumer product comprising the OLEDs described therein, it would have been obvious to one of ordinary skill in the art at the time of the invention to incorporate the OLED devices of Du et al., including the device described in claim 1 above into a consumer product, such as a television or a mobile phone, because the known and primary purpose of such OLED devices is for use in commercial electronic displays, thereby satisfying claim 20.
Allowable Subject Matter
Claims 5-9 and 17-19 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT S LOEWE whose telephone number is (571)270-3298. The examiner can normally be reached on Monday-Friday from 8 AM to 5 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski, can be reached at telephone number 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of an application may be obtained from Patent Center. Status information for published applications may be obtained from Patent Center. Status information for unpublished applications is available through Patent Center for authorized users only. Should you have questions about access to Patent Center, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free).
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) Form at https://www.uspto.gov/patents/uspto-automated- interview-request-air-form.
/Robert S Loewe/Primary Examiner, Art Unit 1766
Prosecution Insights