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 .
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 01/12/2023, 01/12/2023, 01/12/2023, and 01/12/2023 were filed after the mailing date of the instant application on 08/03/2022. The submissions are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Election/Restrictions
In a requirement for election of species, dated 10/29/2025, Applicant was required to choose from:
A compound comprising ligand LA of Formula I wherein,
Species I, wherein M is iridium (claims 1-13 and 17-20),
Species II, wherein M is platinum or palladium (claims 1-11 and 14-20), or
Species III, wherein M is Os, Cu, Ag, or Au, (claims 1-11 and 17-20).
Applicant’s election without traverse of iridium (Species I) in the reply filed on 12/18/2025 is acknowledged.
Claims 14-16 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.
Species I, drawn to claims 1-13 and 17-20, is examined herein.
Specification
The disclosure is objected to because of the following informalities:
The letters, numbers, and/or bonds in the chemical structure given on page 72 are illegible due to poor resolution. Please correct these structures so all letters, numbers, and/or bonds are clearly visible. See the example below.
PNG
media_image1.png
440
770
media_image1.png
Greyscale
Please note that this example is non-limiting and there may be other structures that require correction. Please check all formulae to make sure they are clear. Applicant may wish to make these structures clearer by increasing the size of the structure and/or font, or by making the bond lines thicker.
Appropriate correction is required.
Claim Objections
Claim 7 is objected to because of the following informalities:
With respect to claim 7, there is an unnecessary amount of space between the words “group” and “consisting” in the first line of the claim.
Appropriate correction is required.
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.
Claims 1-13 and 17-20 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.
With respect to independent claims 1, 17, and 20, the claims all require that “two RA or two RB are joined together to form a structure of Formula II fused to A or B”, while simultaneously requiring that “LA does not comprise a structure of Formula II”.
The claims also comprise two structures labelled Formula II, which are pictured below.
PNG
media_image2.png
200
396
media_image2.png
Greyscale
PNG
media_image3.png
454
344
media_image3.png
Greyscale
This introduces uncertainty into the claim because it is unclear which structure the limitation “Formula II” refers to.
In continuing examination, the claims are being interpreted as requiring a structure of the first Formula II fused to one of rings A and B of Formula I, wherein the complete structure of LA, comprising Formula I and the first Formula II, should not be a derivative of the second Formula II.
Claims 2-13 and 18-19 are rejected by virtue of dependency.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 18 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
With respect to claim 18, the claim contains at least one host compound which does not comprise a chemical moiety of parent claim 17. See the example below.
PNG
media_image4.png
154
400
media_image4.png
Greyscale
Please note that this example is non-limiting and there may be other structures that require correction. Please check all formulae to make sure they are in proper dependent form.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 103
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.
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 1-5, 9-12, 17-18, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Nishizeki et al. (JP 2016/219490 A, using the provided translation for references).
With respect to claim 1, Nishizeki discloses compound D-2 ( paragraph 0125), which is pictured below.
PNG
media_image5.png
402
434
media_image5.png
Greyscale
This compound is derived from Nishizeki general equation [3] (paragraphs 0103-0104), which is pictured below.
PNG
media_image6.png
288
318
media_image6.png
Greyscale
In this formula, Nishizeki also teaches that X1 is a nitrogen atom, and forms a pyrazole moiety (paragraph 0105, see also compounds A-5, A-12, A-16, A-19, etcetera).
Such a modification produces a compound with a ligand that meets the requirements of instant Formula I when A is a monocyclic 5-membered (pyrazole) ring, B is a monocyclic 6-membered carbocyclic ring (benzene), Z1 and Z2 are nitrogen atoms and Z3 and Z4 are carbon atoms, K1 and K2 are each a direct bond, RA represents disubstitution of the combination of an aryl and alkyl group, and an alkyl and halogen group, RB is a halogen, and two additional RB are joined to form a structure of Formula II which is fused to ring B. In Formula II, Y is a sulfur atom, and RC represents no substitution. The ligand is complexed to an iridium atom.
Nishizeki includes each limitation claimed, with the only difference between the claimed invention and Nishizeki being a lack of the aforementioned combination of a pyrazole ring and a thiazole-condensed benzimidazole being explicitly stated. Absent a showing of unexpected results, 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 a nitrogen atom from the finite list of possible atoms (C or N) and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a phenylazole organometallic compound condensed with a heteroring (paragraph 0015), which can be used to produce an organic electroluminescent device with high luminescence efficiency, excellent durability, and excellent effect on preventing the occurrence of dark spots and uneven luminescence when having sufficiently shortwave light emission as a blue phosphorescent element (paragraph 0014), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 2, Nishizeki teaches the compound of claim 1, and R, R’, and RC are not present, RA is the combination of an aryl and alkyl group, and alkyl and fluorine, and RB is a fluorine atom, as pictured above.
With respect to claim 3, Nishizeki teaches the compound of claim 1, and ring B is a 6-membered ring, as discussed above.
With respect to claim 4, Nishizeki teaches the compound of claim 1 and Z1 is nitrogen and Z4 is carbon, as discussed above.
With respect to claim 5, Nishizeki teaches the compound of claim 1, and K1 and K2 are both a direct bond, as discussed above.
With respect to claims 9 through 12, Nishizeki teaches the compound of claim 1, and the compound has the formula of Ir(LA)3 wherein p is 3, q is 0, and r is 0 so that ligands LB and LC are not present, as pictured above.
With respect to claim 17, Nishizeki discloses and organic EL device (paragraph 0040) comprising an anode, a cathode, an organic layer between the electrodes (paragraph 0041) and the organic layer comprises a compound of Formula 3 (paragraph 0046), such as compound D-2 (paragraph 0125), which is pictured below.
PNG
media_image5.png
402
434
media_image5.png
Greyscale
This compound is derived from Nishizeki general equation [3] (paragraphs 0103-0104), which is pictured below.
PNG
media_image6.png
288
318
media_image6.png
Greyscale
In this formula, Nishizeki also teaches that X1 is a nitrogen atom, and forms a pyrazole moiety (paragraph 0105, see also compounds A-5, A-12, A-16, A-19, etcetera).
Such a modification produces a compound with a ligand that meets the requirements of instant Formula I when A is a monocyclic 5-membered (pyrazole) ring, B is a monocyclic 6-membered carbocyclic ring (benzene), Z1 and Z2 are nitrogen atoms and Z3 and Z4 are carbon atoms, K1 and K2 are each a direct bond, RA represents disubstitution of the combination of an aryl and alkyl group, and an alkyl and halogen group, RB is a halogen, and two additional RB are joined to form a structure of Formula II which is fused to ring B. In Formula II, Y is a sulfur atom, and RC represents no substitution. The ligand is complexed to an iridium atom.
Nishizeki includes each limitation claimed, with the only difference between the claimed invention and Nishizeki being a lack of the aforementioned combination of a pyrazole ring and a thiazole-condensed benzimidazole being explicitly stated. Absent a showing of unexpected results, 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 a nitrogen atom from the finite list of possible atoms (C or N) and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a phenylazole organometallic compound condensed with a heteroring (paragraph 0015), which can be used to produce an organic electroluminescent device with high luminescence efficiency, excellent durability, and excellent effect on preventing the occurrence of dark spots and uneven luminescence when having sufficiently shortwave light emission as a blue phosphorescent element (paragraph 0014), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Further, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use such a compound in an organic electroluminescent device to produce an organic electroluminescent device with high luminescence efficiency, excellent durability, and excellent effect on preventing the occurrence of dark spots and uneven luminescence when having sufficiently shortwave light emission as a blue phosphorescent element (paragraph 0014), as taught by Nishizeki.
With respect to claim 18, Nishizeki teaches the OLED of claim 17, and Nishizeki also teaches an example of a host compound for the organometallic complex is compound OC-11 (paragraphs 0260 and 0268), which is pictured below.
PNG
media_image7.png
406
648
media_image7.png
Greyscale
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use a host compound with a dibenzofuran or carbazole moiety, as demonstrated by Nishizeki.
With respect to claim 20, Nishizeki discloses a consumer product (a display device or an illumination device, paragraph 0001) which comprises an anode, a cathode, an organic layer between the electrodes (paragraph 0041) and the organic layer comprises a compound of Formula 3 (paragraph 0046), such as compound D-2 (paragraph 0125), which is pictured below.
PNG
media_image5.png
402
434
media_image5.png
Greyscale
This compound is derived from Nishizeki general equation [3] (paragraphs 0103-0104), which is pictured below.
PNG
media_image6.png
288
318
media_image6.png
Greyscale
In this formula, Nishizeki also teaches that X1 is a nitrogen atom, and forms a pyrazole moiety (paragraph 0105, see also compounds A-5, A-12, A-16, A-19, etcetera).
Such a modification produces a compound with a ligand that meets the requirements of instant Formula I when A is a monocyclic 5-membered (pyrazole) ring, B is a monocyclic 6-membered carbocyclic ring (benzene), Z1 and Z2 are nitrogen atoms and Z3 and Z4 are carbon atoms, K1 and K2 are each a direct bond, RA represents disubstitution of the combination of an aryl and alkyl group, and an alkyl and halogen group, RB is a halogen, and two additional RB are joined to form a structure of Formula II which is fused to ring B. In Formula II, Y is a sulfur atom, and RC represents no substitution. The ligand is complexed to an iridium atom.
Nishizeki includes each limitation claimed, with the only difference between the claimed invention and Nishizeki being a lack of the aforementioned combination of a pyrazole ring and a thiazole-condensed benzimidazole being explicitly stated. Absent a showing of unexpected results, 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 a nitrogen atom from the finite list of possible atoms (C or N) and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a phenylazole organometallic compound condensed with a heteroring (paragraph 0015), which can be used to produce an organic electroluminescent device with high luminescence efficiency, excellent durability, and excellent effect on preventing the occurrence of dark spots and uneven luminescence when having sufficiently shortwave light emission as a blue phosphorescent element (paragraph 0014), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Further, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use such a compound in an organic electroluminescent device to produce an organic electroluminescent device with high luminescence efficiency, excellent durability, and excellent effect on preventing the occurrence of dark spots and uneven luminescence when having sufficiently shortwave light emission as a blue phosphorescent element (paragraph 0014), as taught by Nishizeki.
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Nishizeki et al. (JP 2016/219490 A, using the provided translation for references) as applied above, and further in view of Metz et al. (US 2016/0072081 A1).
With respect to claim 19, Nishizeki teaches the OLED of claim 18, as discussed above.
However, Nishizeki does not teach nor fairly suggest any if the instant host materials.
In analogous art, Metz teaches a matrix material for use with an organometallic complex in an electroluminescent device. A preferred embodiment of this matrix material is given on page 17 which is pictured below.
PNG
media_image8.png
119
225
media_image8.png
Greyscale
In this formula, T is a sulfur atom (paragraph 0084).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant application to use the matrix material of Metz as a host compound for the organometallic compound of Nishizeki as Metz teaches that these compounds are suitable matrix materials for use as a host for an emitter compound (paragraph 0090).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Liang et al. (CN 111039987 A) – teaches relevant compounds.
Zhang et al. (CN 113105510 A) – teaches relevant compounds.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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 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.
/RACHEL SIMBANA/Examiner, Art Unit 1786
Prosecution Insights