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
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 1/1/26 has been entered.
Response to Arguments
Applicants arguments and amendments, filed on 1/1/26, have been fully considered but they do not confer patentability on all of the instantly filed claims. Applicants have amended independent claim 1 such that the metal complex is limited to heteroleptic iridium complexes of the formula Ir(La)m(Lb)n(Lc)q wherein ligands La satisfies any one of the compounds of Formulae 2-4, 6, 9, 11, 13, and 15, and wherein ligands Lb and Lc satisfy one of the structures recited in claim 1. The claim amendments overcome the previously relied upon claim objections and 112(b) rejection. The prior art rejection to Fortte et al. (US 2010/0331506) under 102(a)(1) has been withdrawn due to Applicants amendments. However, Fortte et al. is relied upon in an obviousness type rejection as described below. Applicants argue that the iridium complexes taught by Fortte et al. and relied upon in the previous prior art rejection are homoleptic iridium complexes, which are mutually exclusive from the heteroleptic iridium complexes as instantly claimed. While true, Fortte et al. is not limited to homoleptic iridium complexes. The preparation of heteroleptic iridium complexes which satisfy all of the structural limitations of claim 1 is prima facie obvious for reasons described in the new 103 rejection below.
Applicants have further amended the claims in a manner which overcomes the objections to the specification. Applicants have also overcome all of the 112(b) rejections by removing all references to “preferably” and “more preferably”. Applicants have added new claims 24-29 and have canceled claims 2 and 4. Applicants have amended independent claim 1 such that the metal complex is represented by one of Formulae 2-4, 6, 9, 11, 13, and 15. These amendments overcome the previously relied upon prior art rejection to Moon et al. (US 2022/0127288). The metal complexes taught by Moon et al. must adhere to Formula 1 as taught in paragraph 0008. Within the limitations for the variables present in Formula 1 is the requirement that X6 and X7 or X7 and X8 forms a ring (paragraph 0016). Because of Applicants amendments, the metal complexes taught by Moon et al. are mutually exclusive from the metal complexes as recited in independent claim 1.
Claim Objections
Claim 1 is objected to. The limitation “when m is greater than 1” should be amended to “when m is 2” for better clarity. Greater than 1 implies that 2 or more groups are present but claim 1 already limits variable m to be equal to 1 or 2.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 3, 6-14, 17, and 19-27 are rejected under 35 U.S.C. 103 as being unpatentable over Fortte et al. (US 2010/0331506), optionally in view of Tang et al. (Optical Materials 2011, 33, 1291-1296).
Claims 1 and 3: Fortte et al. teaches metal complexes of Formula (1) (paragraph 0032) with at least one ligand satisfying Formula (2) (paragraph 0032). Fortte et al. additionally teaches that a preferred ligand satisfies formula (4a) (paragraph 0065). In formula (4a), variables D’ are each selected from C-H, N, or P with all working examples having one D’ equal to C-H and one D’ equal to N. Specific metal complexes are recited in paragraph 0085. The explicitly taught iridium complexes include both homoleptic and heteroleptic iridium complexes. Specific complexes which comprise a ligand which satisfies ligand La of claim 1 are complexes 88 and 91 which have the respective structures
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and
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. While Fortte et al. does not teach heteroleptic complexes comprising these ligands, it would have been obvious to one having ordinary skill in the art to have prepared heteroleptic iridium complexes which comprise a ligand satisfying LA of claim 1 and at least one ligand which satisfies one of ligands Lb or Lc given the overall teachings of Fortte et al. Fortte et al. explicitly teaches heteroleptic iridium complexes where the ancillary ligands include 2-phenylpyridine and acetylacetonate based ligands. One having ordinary skill in the art would understand that the various ligands disclosed therein may be combined with a ligand satisfying Formula LA above. The reason/motivation for preparing heteroleptic complexes would be to tune/alter the photoluminescent properties. One of ordinary skill in the art would have a reasonable expectation of success since as Fortte et al. teaches many different heteroleptic iridium complexes which are useful as phosphorescent dopant materials. The ancillary ligands disclosed in the complexes of Fortte et al. are well-known ligands and such ligands is within the palette of ligands available to a person of ordinary skill in the art. Replacing one or two of the ligands in the complexes shown above with one of the ancillary ligands disclosed by Fortte et al., including 2-phenylpyridine or acetylacetonate, would be expected to produce predictable changes in the HOMO/LUMO levels of the phosphorescent dopant, and thus the emission color, which is a known effect in the art.
While Fortte et al. alone is believed to render obvious the preparation of heteroleptic iridium complexes which satisfy claim 1, further motivation to prepare such complexes can be found in Tang et al. Fortte et al. and Tang et al. are combinable as they are both from the same field of endeavor of organic electroluminescent devices. Tang et al. teaches that heteroleptic iridium complexes offer several advantages to homoleptic iridium complexes such as easy preparation, easy tuning of solubility and photophysical properties through the introduction of various ancillary ligands (page 1291). Given this teaching, one having ordinary skill in the art would look to prepare heteroleptic complexes, including heteroleptic complexes of complexes 88 and 91 of Fortte et al. by including any of the explicitly taught ancillary ligands of Fortte et al. for the reasons provided by Tang et al. This includes preparing the iridium complexes
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and
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where n is equal to 1 or 2, m is equal to 1 or 2, and q is equal to 1 or 2 with m + n = 3 and m + q = 3, and 3 being the oxidation state of the Ir. As applied to claim 1, the above complexes have the formula Ir(La)m(Lb)n with Lb satisfying the 5th ligand and the last ligand recited for Lb with Xc and Xd equal to O, Ra and Rb equal to methyl, and Rc equal to hydrogen. Ligand La in the above complexes satisfies Formula 2 of claims 1 and 3 with X1 through X8 equal to CRx with all Rx equal to hydrogen atoms, and Y is equal to CRyRy with both Ry equal to fluorine.
Claim 6: In the complexes above, all X groups are equal to CRx, thereby satisfying claim 6.
Claim 7: In the complexes above Rx, Ry, and Rz are equal to one of hydrogen, halogen, and alkyl, thereby satisfying claim 7.
Claims 8-11 and 24-27: In the complexes above, all of X1-X8 are equal to CRx, and all Rx are equal to hydrogen atoms, thereby satisfying claims 8-11 and 24-27.
Claims 12, 13, and 17: While Fortte et al. does not explicitly teach any metal complexes which satisfy claims 12, 13, and 17, the overall teachings of Fortte et al. render obvious to one having ordinary skill in the art to prepare such complexes. For example, the metal complex 88 has variable Y equal to CRyRy with both Ry equal to fluorine. However, variable Y is taught by Fortte et al. to include the groups taught in paragraph 0034 and includes the groups -O-, -S-, and -Se-. Preparing a compound according to complex 88 with variable Y equal to O, S, or Se is within the level of one having ordinary skill in the art. Additionally, complexes where variable Y is equal to O are exemplified by Fortte et al. Therefore, the preparation of a metal complex which is analogous to complex 88 but with -O- present instead of -CF2- is prima facie obvious to one having ordinary skill in the art. Such a metal complex satisfies the limitations of claims 12, 13, and 17.
Claim 14: The complexes rendered obvious as described in claim 1 above have the formula M(La)m(Lb)n(Lc)q with n equal to 1 or 2, m equal to 1 or 2, M being equal to Ir, and ligands La and Lb being a ligand described in claim 1 above, thereby satisfying claim 14.
Claims 19, 20, and 22: The metal complexes taught by Fortte et al. are employed as phosphorescent dopants in organic light-emitting devices (example 7). The organic light-emitting devices are comprised of an anode, a hole transport region, an emission layer comprising a host material and said dopant, an electron transport region, and a cathode. The employment of any one of the phosphorescent metal complexes explicitly taught by Fortte et al., including the metal complexes which are rendered obvious by Fortte et al. (optionally evidenced by Tang et al.) and shown in claim 1 above, in the same manner as taught in example 7, is prima facie obvious to a person having ordinary skill in the art, thereby satisfying claims 19, 20, and 22.
Claim 21: Because the metal complexes taught and suggested by Fortte et al. as described in claim 1 above satisfy all of Applicants structural limitations of claim 1, it necessarily follows that any physical property claimed by Applicants regarding Formula 1 but not explicitly taught by Fortte et al. would inherently be present. A chemical compound and its properties are inseparable.
Claim 23: The act of preparing any one of the metal complexes suggested by Fortte et al. and described in claim 1 above would require forming a crude reaction mixture comprising one of these complexes, which is in itself, a compound composition, thereby satisfying claim 23. Additionally, the act of characterizing either of these metal complexes via customary methods such as NMR would require a solvent, which also results in a compound combination which satisfies claim 23.
Allowable Subject Matter
Claims 5, 15, 18, 28, and 29 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. To arrive at metal complexes which satisfy claims 5, 15, 18, 28, and 29 given the teachings of Fortte et al. with or without the teachings of Tang et al., as described above would require the use of improper hindsight reconstruction.
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.
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/Robert S Loewe/Primary Examiner, Art Unit 1766