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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 07/20/2026 has been entered.
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.
Claim 32 is 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.
In reference to claim 32, the claim limits the hole transport layer which lacks antecedent basis in the claim. That is, claim 2 from which claim 32 does not comprise a hole transport layer.
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 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, 4, 7-10, 12-15, 17, 20, 22-26, 28-29 and 31-33 are rejected under 35 U.S.C. 103 as being unpatentable over Hartmann et al (US 2013/0099209) (Hartmann) as evidenced by Irak et al (J. Chil. Chem. Soc., (64)1 2019,p. 4303-9.) (Irak).
In reference to claims 1, Hartmann teaches an organic electronic device comprising an anode, a hole transport layer, an organic active layer, an electron injection layer and a cathode (Hartmann [0079]) wherein the hole transport layer is comprised of materials such as Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile (Hartmann, [0060]) that is doped with a square planar copper complex that is a p-type dopant such as Cu(tfac)2 (Hartmann Table 2; examples 4 and 5).
PNG
media_image1.png
242
256
media_image1.png
Greyscale
PNG
media_image2.png
104
280
media_image2.png
Greyscale
While Hartmann does not exemplify a device with this taught dopant and this taught hole transport material, it would have been obvious to have selected from a list of hole transport materials to have arrived at the a functional device using a dopant that can be processed by liquid or gas phased techniques and that is inexpensive and commercially available due to its use in the semiconductor industry (Hartmann, [0028] [0075]).
While Hartmann does not expressly teach that the Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile has a HOMO energy as claimed, the HOMO energy of a material is an inherent property of the molecule. As evidence to that fact, Irak teaches the HOMO energy of this compound is -7.47 as calculated by DFT calculations, which puts its HOMO much further from vacuum than the claim requirement (Irak, Table 1).
For Claim 1: Reads on a device as claimed with an anode and cathode and the hole transport layer reads on a hole injection layer with a hole transport compound of Pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile comprising C, H and N covalently bound, Cu(tfac)2 reads on a metal complex of formula IId wherein M is Cu, n is 2, A1 CF3 and A2 is CH3.
For Claim 4: Reads on where the layer is non-emissive.
For Claim 7: Reads on a transition metal.
For Claim 8: Reads on 369.7 g/mol.
For Claim 9: Reads on at least 3 carbon atoms.
For Claim 10: Reads on where the metal complex is non emissive.
For Claim 12: Reads on from 1 to 6 aromatic fused ring systems comprising heteroaromatic rings.
For Claim 13: Reads on 4 fused aromatic rings.
For Claim 14: Reads on at least 1 unsaturated 6 membered ring comprising a hetero atom.
For Claim 15: Reads on N.
For Claim 20: Reads on wherein n is 2.
For Claim 22: Reads on A1 CF3 and A2 is CH3.
For Claim 23: Reads on G61.
For Claim 24: The organic active layer reads on a photoactive layer.
For Claim 25: Reads on an emission layer.
For Claim 31: Reads on a light emitting device.
For Claim 32: Reads on wherein the layers are the same.
For Claim 33: Reads on wherein A3 is hydrogen.
For Claim 26, 28 and 29, Hartmann teaches the device as described above for claim 1. While Hartmann does not describe the HTL layer as comprising two sublayers, it meets the requirements of two layers as the layers do not have to have mutually exclusive compositions.
Claims 2, 5, 6, 11, and 16-19 are rejected under 35 U.S.C. 103 as being unpatentable over Hartmann et al (US 2013/0099209) (Hartmann) and further in view of Nikiforov (Organic Electronics (36) 2016, 120-132).
In reference to claims 2, 5, 6, 11, and 16-19, Hartmann teaches the device as described above for claim 1. Hartmann generally teaches that teaches known hole transport layer materials can be used such as several examples (Hartmann [0030] to [0068]) but is not limited thereto and exemplifies in examples NPB. Hartmann does not expressly teach a compound that meets the claim requirements.
With respect to the difference, Nikiforov teaches, in analogous art that CBP can be used as a p-doped hole transport layer material as an alternative to NPB in similar devices (Nikiforov p 121, col 1-2 and p 130 col 1-2).
That is, the substitution of the CBP of Nikiforov for the hole transport layer material of Hartmann, absent unexpected results, would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application with the predictable result of efficiently transporting electrons away from the emission layer. The simple substitution of one known element for another is likely to be obvious when predictable results are achieved. See KSR International Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395 – 97 (2007) (See MPEP § 2143, B).
For Claim 2: Reads on wherein k, p and r are each 1, Ar1 and Ar6 is carbazole, Ar3 and Ar4 are phenyl.
For Claim 5: Reads on wherein k, p and r are each 1, Ar1 and Ar6 is carbazole, Ar3 and Ar4 are phenyl.
For Claim 6: Reads on 484.59 g/mol.
For Claim 11: Reads on wherein k, p and r are each 1, Ar1 and Ar6 is carbazole, Ar3 and Ar4 are phenyl.
For Claim 16: Reads on no N atoms that are not part of an aromatic ring.
For Claim 17: Reads on 8 aromatic rings.
For Claim 18: Reads on D2.
For Claim 19: Reads on F9.
Claim 27 are rejected under 35 U.S.C. 103 as being unpatentable over Hummert et al as evidenced by Irak et al (J. Chil. Chem. Soc., (64)1 2019, p. 4303-9.) (Irak) and further in view of Pentlehner et al (US 20200185624) (Pentlehner).
In reference to claim 27, Hartmann teaches the device as described above for claim 1. Hartmann does not expressly teach a sublayer comprising of only the p-dopant. However, such a configuration is well known in the art.
With respect to the difference, Pentlehner teaches, in analogous art, metal complexes in OLED devices and specifically teaches that they can be used in a hole injection layer that either comprises such metals as a dopant or a hole injection layer that consists of a p-dopant alone (Pentlehner [2104]).
That is, the substitution of the layer configuration of Pentlehner for the layer configuration of Hartmann, absent unexpected results, would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application with the predictable result of efficiently transporting electrons away from the emission layer. The simple substitution of one known element for another is likely to be obvious when predictable results are achieved. See KSR International Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395 – 97 (2007) (See MPEP § 2143, B).
Response to Arguments
Applicant’s arguments with respect to the claims have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Sean M DeGuire whose telephone number is (571)270-1027. The examiner can normally be reached Monday to Friday, 7:00 AM - 5:00 PM.
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 A. 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.
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.
/Sean M DeGuire/Primary Examiner, Art Unit 1786
Prosecution Insights