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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 12/11/25 has been entered.
Response to Arguments
Applicants arguments and amendments have been fully considered but they do not confer patentability on all of the instantly filed claims. Applicants have amended independent claims 1, 17, and 20 . These claims include the limitation that when LB and LC are each independently bidentate ligands, and neither LB nor LC has the structure
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. Claims 1, 17, and 20 have further been amended such that in proviso (iv) each of R and R’ is not H or D. Proviso (vi) has been removed from claims 1, 17, and 20. Last, new dependent claims 22-27 have been added.
The prior art rejection to Cho et al. (KR-20150115975) has been withdrawn since the compound disclosed in Cho et al. has an acetylacetonate ligand, which has been excluded from Applicants claims as described above.
The prior art rejection and double patenting rejections to Kottas et al. (US Pat. 8,709,615) are wholly maintained, as described below. Additionally, a new prior art rejection is presented below.
Claim Rejections - 35 USC § 112
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.
Claim 16 is rejected under 35 U.S.C. 112(d) 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. Claim 16 is drawn to a tetradentate Pt or Pd complex of Formula V. In such instances, variable p is equal to 1, and variables q and r are both equal to zero. This means that in Formula V, the oxidation state of Pd or Pt must be equal to one. All embodiments of Formula would necessarily result in Pt(II) or Pd(II) complexes, which do not satisfy the expression p + q + r, which is necessarily equal to 1. Moreover, there are no known, stable tetravalent platinum and palladium complexes with a Pt(I) or Pd(I) oxidation state. Applicant may cancel the claim, amend the claim to place the claim in proper dependent form, rewrite the claim in independent form, or present a sufficient showing that the dependent claim complies with the statutory requirements. Should Applicants remove the limitation “p+q+r is the oxidation state of the metal M” from claim 1, this rejection would be withdrawn.
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 1-6, 13, 17, 18, 20, and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Kottas et al. (US Pat. 8,709,615).
Claims 1 and 21: Kottas et al. teaches an iridium complex having the formula
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where X is selected from, inter alia, GeRR’. On its face, the teachings of Kottas et al. cannot be relied upon to satisfy provisos (i)-(iii), (v), and (vi). However, proviso (iv) requires that R and R’ are not H or D. Given the overall teachings of Kottas et al., embodiments where variable X is equal to GeRR’ would not be limited to the narrow embodiments where GeRR’ is equal to GeH2, GeD2, or GeHD, but rather to the entirety of embodiments as explicitly taught by Kottas et al. Variables R and R’ are not limited to H and D, but are part of a much large Markush group. In fact, the relative number of compounds where R and R’ are equal to H and/or D represents small fraction of the total number of compounds which may be envisioned by the Markush group for R and R’ as taught by Kottas et al. For this reason, the teachings of Kottas et al. render obvious to one having ordinary skill in the art the preparation of compounds where X is equal to GeRR’ and where R and R’ are not selected from hydrogen or deuterium.
And while the Examiner has determined that only through the use of improper hindsight reconstruction would compounds satisfying claim 11 be envisioned from the teachings of Kottas et al., there is nothing recited in Kottas et al. which would limit one having ordinary skill in the art to only select hydrogen or deuterium as R and R’ when Kottas et al. clearly teaches many other possible variable selections besides hydrogen and deuterium. For this reason, a compound which adheres to the general formula above with X equal to GeRR’ and R and R’ is not hydrogen or deuterium would have been obvious to one having ordinary skill in the art.
Claim 2: The complex above where X is GeRR’ has RA equal to hydrogen and alkyl (as recited in claim 1 of Kottas A), those RB groups which are not bonded to form a group of Formula IV being equal to hydrogen, thereby satisfying claim 2.
Claims 3 and 4: The complex above where X is GeRR’ has moiety A equal to pyridine which satisfies claim 3 and the first structure of claim 4 with all X13-X16 equal to C, three RAA equal to hydrogen, and the RAA bonded to X15 being equal to alkyl.
Claims 5 and 6: The complex above where X is GeRR’ satisfies the second formula of claim 5 with all X1-X8 groups equal to C (which satisfies claim 6), all RE being equal to hydrogen, and Y’ being equal to Ge which also satisfies claim 10.
Claim 13: Ligand LB in Formula I of Kottas et al. reads on the 5th ligand recited in claim 13.
Claim 17: The rejection of claim 1 above is wholly incorporated into claim 17. Claim 8 of Kottas A includes everything that claim 1 of Kottas et al. has but is drawn to an organic light emitting device comprising an anode, a cathode, and an organic layer comprising a compound of Formula I. For the same reasons as claim 1, claim 8 of Kottas et al. satisfies claim 16 of the instant application.
Claim 18: Claims 15 and 16 of Kottas et al. are drawn to an organic light emitting device comprising a host material, wherein the host material comprises groups which satisfies claim 18.
Claim 20: The rejection of claims 1 and 17 above are wholly incorporated into the rejection of claim 20. Claim 9 of Kottas et al. is drawn to a consumer product of claim 8, thereby satisfying claim 20 of the instant application.
Claim 22: Kottas et al. teaches specific iridium complexes shown in the table starting with compound 53 and ending with compound 1146. The preparation of an analog of these compounds having GeRR’ instead of O is prima facie obvious to one of ordinary skill in the art given the teachings of Kottas et al. This includes ligands which satisfy LB1, LB3, LB7, and LB19 as shown in compounds 53, 157-159, 165, 314, 321, 625, 626, 627, 628, 633, 1145, and 1146.
Claims 1-6, 13, 17, 18, 20, 21, 22, and 26 are rejected under 35 U.S.C. 103 as being unpatentable over Ji et al. (US 2019/0051844).
Claims 1, 21, and 26: Ji et al. teaches iridium complexes of the formula Ir[LA]y[LB]x where ligand LA has the formulae
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and ligand LB has the formula
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(abstract). Ji et al. teaches that X may be GeRR’ (paragraph 0019). Additionally, paragraph 0073 teaches specific ligands LA where X is selected from O, S, C(CH3)2, N(CH3), or Si(CH3)2. While X in paragraph 0073 does not include GeRR’, the overall teachings of Ji et al. would have rendered obvious the preparation of a ligand LA where X is equal to GeRR’ as such an embodiment is explicitly taught in paragraph 0019. Moreover, one having ordinary skill in the art would have understood that when employing X as GeRR’, the obvious selection of R and R’ being equal to methyl is realized given the teachings of paragraph 0073. The substitution of geranium for silicon would have been a predictable variation to one of ordinary skill in the art as they both belong in Group 14 of the periodic table, also known as the carbon group. And given that the preferred R and R’ groups in the ligands taught in paragraph 0073 is methyl, preparing analogs of the ligands taught in paragraph 0073 where X is equal to Ge(CH3)2 would have been the most obvious embodiment when selecting X to be equal to GeRR’. Therefore, preparing a ligand LA1 through LA181 where X is equal to Ge(CH3)2 is obvious to one having ordinary skill in the art given the overall teachings of Li et al. This includes, as one example, preparing a ligand which has the structure
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where X is equal to Ge(CH3)2. As applied to claim 1, a complex comprising such a ligand has the formula Ir[LA]y[LB]x with LA satisfying Formula III and LB being a phenyl-pyridine based ligand as taught in the abstract. As applied to Formula III of claim 1, the ligand shown above has Z1 equal to N, Z2 equal to C, ring A equal to benzene, all available RA groups equal to hydrogen, ring B equal to benzene, and two adjacent RB groups are joined to form a structure of Formula IV with Y equal to Ge(CH3)2, Z3 and Z4 equal to C, and the two adjacent RC groups forming an unsubstituted benzene ring, all other available RB groups equal to hydrogen, and K equal to a single bond. The ligand described above satisfies proviso (iv) of claim 1 as both R and R’ are not H or D (which also satisfies claim 21). Additionally, ligands LA21 through LA30, LA41 through LA61, and L81 through LA89 in which X is equal to Ge(CH3)2 also satisfy proviso (iii) as the ring of moiety B that is bonded to K is tri-substituted, which satisfies claim 26. Further, ligands LA118 through LA141 do not apply to any of provisos (i) through (v) as said ligands have a different bonding pattern.
Claim 2: The complex above where X is Ge(CH3)2 has RA equal to hydrogen, those RB groups which are not bonded to form a group of Formula IV being equal to hydrogen, thereby satisfying claim 2.
Claims 3 and 4: The complex above where X is Ge(CH3)2 has moiety A equal to pyridine which satisfies claim 3 and the first structure of claim 4 with all X13-X16 equal to C, and all RAA equal to hydrogen.
Claims 5 and 6: The complex above where X is Ge(CH3)2 satisfies the second formula of claim 5 with all X1-X8 groups equal to C (which satisfies claim 6), all RE being equal to hydrogen, and Y’ being equal to GeRR’ with R and R’ equal to methyl.
Claim 13: Ligand LB in the complexes taught by Ji et al. have the structure
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as taught in the abstract. This structure is the same as the 4th structure recited in claim 13.
Claim 17: The rejection of claim 1 above is wholly incorporated into the rejection of claim 17. The iridium complexes taught by Ji et al. are employed in organic electroluminescent devices as a phosphorescent dopant. The exemplified devices comprises an anode, a hole transport region, an emission region comprising a host material and said phosphorescent dopant, an electron transport region, and a cathode. The preparation of an organic electroluminescent device comprising any one of the compounds taught and suggested by Ji et al., including the ones described above, would have been prima facie obvious to one having ordinary skill in the art, thereby satisfying claim 17.
Claim 18: Ji et al. teaches that the host materials present in the emission layer include those which satisfy claim 18 (see claim 16 of Ji et al.).
Claim 20: The rejection of claims 1 and 17 above are wholly incorporated into the rejection of claim 20. Ji et al. teaches and claims consumer products which comprise the organic light-emitting devices taught therein (claim 18 of Ji et al.) thereby satisfying claim 20.
Claim 22: The ligands LB taught by Ji et al. all adhere to general formula
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as taught in the abstract. The exemplified ligand LB is the same as ligand LB1 of claim 22. Preparation of an iridium complex where X is equal to Ge(CH3)2 and ligand LB is 2-phenylpyridine would have therefore been prima facie obvious to one having ordinary skill in the art, thereby satisfying claim 22.
Double Patenting
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 claims at issue 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); and In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on a nonstatutory double patenting ground provided the reference application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form 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 http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1-6, 10, 12-14, and 17-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 8, 9, and 13-16 of U.S. Patent No. 8,709,615. Although the claims at issue are not identical, they are not patentably distinct from each other.
Claim 1 of the ‘615 patent claims a compound where X is selected from GeRR’ and satisfies the limitations of instant claims 1-6, 10, and 12-14. Claim 8 of the ‘615 patent claims a light emitting device comprising a compound where X is selected from GeRR’ and satisfies the limitations of instant claims 17-19. Claim 9 of the ‘615 patent claims a consumer product comprising a light emitting device comprising a compound where X is selected from GeRR’ and satisfies the limitations of instant claim 20. The 103 rejection of Kottas A above may be relied upon herein for further details. The scope of the R and R’ variables as described in the claims of the ’615 application allow for embodiments where both R and R’ are not equal to H or D.
Allowable Subject Matter
Claims 11 and 15 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 for reasons already of record. Newly added claims 23-25 and 27 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.
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/Robert S Loewe/Primary Examiner, Art Unit 1766