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 10/04/2023 and 10/04/2023 were filed after the mailing date of the instant application on 10/04/2023. The submissions are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Specification
The disclosure is objected to because of the following informalities:
The letters, numbers, and/or bonds in the chemical structure given in paragraphs [0134] and [0135] 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
416
368
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 19 is objected to because of the following informalities:
The letters, numbers, and/or bonds in the chemical structure given in claim 19 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
416
368
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 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 1-20 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 claim 1, the claim contains the limitation,
PNG
media_image2.png
56
740
media_image2.png
Greyscale
This introduces uncertainty into the claims because X is defined as CRX.
In continuing examination, this is being interpreted as a simple typographical error, wherein CR is meant to be CRX.
Claims 2-20 are rejected by virtue of dependency.
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 1-4 and 9-13 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ohsawa et al. (US 2015/0073142 A1).
With respect to claims 1-4, Ohsawa discloses Compound (115) (page 13), which is pictured below.
PNG
media_image3.png
232
344
media_image3.png
Greyscale
This compound meets the requirements of condition (1) of the instant claim when each of X1-X6 is carbon, K is a direct bond, LA is coordinated to an iridium atom, R1 is a C6 aryl (phenyl) group which is substituted at the para position with a C1 alkyl (methyl) group, and RA and RB represent no substitution. All other groups are either hydrogen atoms or not present.
With respect to claim 9, Ohsawa teaches the compound of claim 1, and R2 is not present.
With respect to claim 10, Ohsawa teaches the compound of claim 1, and ligand LA has the structure of the first embodiment of the claim.
With respect to claim 11, Ohsawa teaches the compound of claim 1, and ligand LA has the structure of the last embodiment of the claim.
With respect to claim 12, Ohsawa teaches the compound of claim 1, and ligand LA has the structure of instant ligand LA2(R2)(R2)(R1)(R1).
With respect to claim 13, Ohsawa teaches the compound of claim 1, and the compound has the formula Ir(LA)2(LB).
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 1-15 and 17-20 are rejected under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2017/0077425 A1).
With respect to claims 1-4, Ma discloses Comp (LA1)2Ir(LB196) (page 16), which is pictured below.
PNG
media_image4.png
392
504
media_image4.png
Greyscale
This compound is derived from Ma formula M(LA)x(LB)y(LC)z, wherein all ligands are derived from the phenylpyridine derivative shown below (paragraph 0016).
PNG
media_image5.png
282
138
media_image5.png
Greyscale
In this formula, Ma teaches that each of X1 to X13 are a carbon or a nitrogen atom.
When X2 is selected as a nitrogen atom, it forms a compound which meets the requirements of condition (1) of the instant claim when each of X1-X6 is carbon, K is a direct bond, LA is coordinated to an iridium atom, R1 is a C6 aryl (phenyl) group which is substituted at the para position with a C5 alkyl (neopentyl-α,α-d2) group, and RA and RB represent no substitution. All other groups are either hydrogen atoms or not present.
Ma includes each element claimed, with the only difference between the claimed invention and Ma being a single nitrogen atom. 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 carbon or nitrogen atom at the required location since the combination of elements would have yielded the predictable result of an emitter which has a more parallel orientation factor as a result of the steric bulkiness from the substituent, which has increased external quantum efficiency (paragraph 0131), and which can be used at a higher concentration due to decreased self-quenching, resulting in increased emitter PLQY (paragraph 0132), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claims 5-7, Ma teaches the compound of claim 1, as discussed above.
Ma also teaches that ligand LA may be represented by the structure below (paragraph 0016).
PNG
media_image6.png
418
272
media_image6.png
Greyscale
In this formula, X2 is nitrogen, X1 and X3-X10 are carbon atoms (paragraph 0017), and X is an oxygen atom (paragraph 0018).
Such a modification produces a compound that meets the requirements of the instant claim when two RB are joined to form a structure of Formula II, wherein Y is oxygen, X is CRX, and RX and R2 are joined to form a fused benzene ring.
Ma includes each element claimed, with the only difference between the claimed invention and Ma being a lack of the aforementioned specific ligand being used. 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 any taught ligand from the finite list of possible ligands since the combination of elements would have yielded the predictable result of an emitter which has a more parallel orientation factor as a result of the steric bulkiness from the substituent, which has increased external quantum efficiency (paragraph 0131), and which can be used at a higher concentration due to decreased self-quenching, resulting in increased emitter PLQY (paragraph 0132), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 8, Ma teaches the compound of claim 5, and Ma also teaches that the materials may be further modified to have better solution processing by adding substituents such as aryl because such structures demonstrate a lower tendency to recrystallize (paragraph 0089, lines 23-33).
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 add an aryl substituent to the ligand of Ma in order to lower the tendency for the compound to recrystallize during solution processing, as taught by ma.
With respect to claim 9, Ma teaches the compound of claim 1, and R2 is an alkyl group which combines with RX to form a fused ring structure, as discussed above.
With respect to claim 10, Ma teaches the compound of claim 1, and the ligand LA has the structure of the first embodiment of the claim, as pictured above.
With respect to claim 11, Ma teaches the compound of claim 1, and the ligand LA has the structure of the last embodiment of the claim.
With respect to claim 12, Ma teaches the compound of claim 1, and the ligand LA has the structure of instant LA2(R1)(R15)(R1)(R1), as pictured above.
With respect to claims 13, Ma teaches the compound of claim 1, and the compound has the formula Ir(LA)(LB)2, as pictured above.
With respect to claims 14 and 15, Ma teaches the compound of claim 13, and LB has the structure of the first embodiment on the second row of the instant claim when all Y characters are CH, K1’ is a direct bond, and Ra and Rb are no substitution, as pictured above. Ligand LC is absent.
With respect to claim 15, Ma teaches the compound of claim 13, and the compound has the formula Ir(LA)(LB)2, when k is 2 and LB has the structure of instant LB1, as pictured above.
With respect to claim 17, Ma teaches the compound of claim 1, and Ma also teaches an organic light emitting device comprising an anode, a cathode, and an organic layer between the anode and cathode and the organic layer comprises the compound (paragraph 0035).
With respect to claims 18 and 19, Ma teaches the OLED of claim 17, and Ma also teaches that the organic layer may comprise a host (paragraph 0220), such as the compound pictured below, which comprises a dibenzothiophene moiety, and meets the requirements of the third embodiment on the second row on page 195 of the instant claim (dated 10/04/2023), when all X characters are carbon atoms, YA is sulfur, and RA’-RD’ represent no substituent.
PNG
media_image7.png
172
298
media_image7.png
Greyscale
With respect to claim 20, Ma teaches the compound of claim 1, and Ma also teaches a consumer product, such as a lighting panel, comprising a cathode, an anode, and an organic layer, and the organic layer comprises the compound (paragraph 0219).
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 the compound in a consumer product, such as a lighting panel, with the claimed device structure, as taught by Ma.
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2017/0077425 A1) as applied above, and further in view of Inoue et al. (US 2015/0005496 A1).
With respect to claim 16, Ma teaches the compound of claim 1, as discussed above.
However, while Ma teaches that the phenyl substituent on the pyrimidine moiety may be further substituted by a deuterated alkyl group (see for example the formulae in paragraph [0029] and the definition of R6 in paragraph [0034]), Ma does not fairly suggest such a selection.
In analogous art, Inoue teaches an iridium organometallic complex comprising a phenylpyrimidine ligand wherein the pyrimidine portion of the ligand comprises a phenyl substituent and the phenyl substituent is substituted at the 2 and 6-positions.
Inoue teaches that when a phenyl group whose 2 and 6-positions are each substituted by an alkyl group is bonded to the 4-position of a pyrimidine skeleton, a broad electron distribution caused by conjugation between the pyrimidine skeleton and the phenyl group can be prevented, thus, the spectrum derived from the complex can be narrower than that of an organometallic iridium complex that is not substituted this way. As a result, emission efficiency is increased (paragraph 0055).
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 include alkyl groups, deuterated or otherwise, at the 2 and 6-positions of the phenyl substituent on the ligand of Ma in order to prevent a broad electron distribution caused by conjugation between the pyrimidine skeleton and phenyl group, narrowing the spectrum of the organometallic complex, and increasing the emission efficiency, as taught by Inoue.
Such a modification produces the first compound in the second row on page 191 of the instant claims (dated 10/04/2023).
PNG
media_image8.png
208
312
media_image8.png
Greyscale
Double Patenting
A rejection based on double patenting of the “same invention” type finds its support in the language of 35 U.S.C. 101 which states that “whoever invents or discovers any new and useful process... may obtain a patent therefor...” (Emphasis added). Thus, the term “same invention,” in this context, means an invention drawn to identical subject matter. See Miller v. Eagle Mfg. Co., 151 U.S. 186 (1894); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Ockert, 245 F.2d 467, 114 USPQ 330 (CCPA 1957).
A statutory type (35 U.S.C. 101) double patenting rejection can be overcome by canceling or amending the claims that are directed to the same invention so they are no longer coextensive in scope. The filing of a terminal disclaimer cannot overcome a double patenting rejection based upon 35 U.S.C. 101.
Claims 1-11, 13-15, and 17-20 are provisionally rejected under 35 U.S.C. 101 as claiming the same invention as that of claims 1-11, 13-15, and 17-20 of copending Application No. 18/627,982 (reference application).
The wording, structures, formulae, limitations, and wording of claims 1-11, 13-15, and 17-20 of ‘982 are either identical to each corresponding claim in the instant application, or the claims differ in their wording, but still contain the same limitations listed in the alternative. The substance of the claims is identical.
This is a provisional statutory double patenting rejection since the claims directed to the same invention have not in fact been patented.
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Yoo et al. (KR 2018/0064216 A, translation provided) – teaches phenylpyridine ligands with a 5-membered heterocycle condensed to the benzene portion of the ligand.
Seo et al. (US 2017/0288154 A1) – teaches an iridium phenyl-pyrimidine ligand wherein the substituent on the pyrimidine group causes the HOMO to be distributed over the first ligand and the LUMO to be distributed over the ancillary phenylpyridine ligand.
Dyatkin et al. (US 2021/0188888 A1) -teaches an iridium organometallic complex with a dibenzoheterole group wherein the pyridine/pyrimidine portion has a steric polyphenylene substituent.
Li et al. (US 2018/0159051 A1) – teaches iridium organometallic complexes with polyphenylene luminophore substituents.
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/Primary Examiner, Art Unit 1786
Prosecution Insights