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 .
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.
Response to Amendment
The amendment of 12 September 2025 has been entered.
Disposition of claims:
Claims 3-4, 6, 8, 11-13, and 16 have been amended.
Claims 1-2, 5, 7, 14-15, and 17-20 are cancelled.
Claims 21-22 are new.
Claims 3-4, 6, 8-13, 16, and 21-22 are pending.
The amendment to the abstract has overcome the objection set forth in the last Office action. The objection has been withdrawn.
The amendment to claim 13 has overcome the objection to claim 13 set forth in the last Office action. The objection has been withdrawn.
The amendment to claim 3 has overcome the rejections of claims 1-4, 7-12, and 14-18 under 35 U.S.C. 103 as being unpatentable over Tsujimoto et al. (“Pure red electrophosphorescence from polymer light-emitting diodes doped with highly emissive bis-cyclometalated iridium(III) complexes” Journal of Organometallic Chemistry, vol. 695 (2010) pp. 1972-1978.) (hereafter “Tsujimoto”) in view of Fukuzaki et al. (US 2011/0049496 A1) (hereafter “Fukuzaki”) set forth in the last Office action as well as the rejections of claims 5-6 under 35 U.S.C. 103 as being unpatentable over Tsujimoto et al. (“Pure red electrophosphorescence from polymer light-emitting diodes doped with highly emissive bis-cyclometalated iridium(III) complexes” Journal of Organometallic Chemistry, vol. 695 (2010) pp. 1972-1978.) (hereafter “Tsujimoto”) in view of Fukuzaki et al. (US 2011/0049496 A1) (hereafter “Fukuzaki”), and further in view of Li et al. (US 2002/0076576 A1) (hereafter “Li”) set forth in the last Office action. The rejections have been withdrawn. However, as outlined below, new grounds of rejection have been made.
The amendment to claim 3 has overcome the provisional rejection of claims 1-7 and 10-12 on the ground of nonstatutory double patenting as being unpatentable over claim 11 of copending Application No. 18/038,672 (reference application) set forth in the last Office action. The provisional rejection has been withdrawn.
Response to Arguments
Applicant’s arguments that the amendments to the claims have overcome the rejections of claims 1-4, 7-12, and 14-18 under 35 U.S.C. 103 as being unpatentable over Tsujimoto et al. (“Pure red electrophosphorescence from polymer light-emitting diodes doped with highly emissive bis-cyclometalated iridium(III) complexes” Journal of Organometallic Chemistry, vol. 695 (2010) pp. 1972-1978.) (hereafter “Tsujimoto”) in view of Fukuzaki et al. (US 2011/0049496 A1) (hereafter “Fukuzaki”) set forth in the last Office action as well as the rejections of claims 5-6 under 35 U.S.C. 103 as being unpatentable over Tsujimoto et al. (“Pure red electrophosphorescence from polymer light-emitting diodes doped with highly emissive bis-cyclometalated iridium(III) complexes” Journal of Organometallic Chemistry, vol. 695 (2010) pp. 1972-1978.) (hereafter “Tsujimoto”) in view of Fukuzaki et al. (US 2011/0049496 A1) (hereafter “Fukuzaki”), and further in view of Li et al. (US 2002/0076576 A1) (hereafter “Li”) set forth in the last Office action 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.
Applicant's arguments filed 12 September 2025 with respect to the rejections of claims 1-4, 7-12, and 14-18 under 35 U.S.C. 103 as being unpatentable over Tsujimoto et al. (“Pure red electrophosphorescence from polymer light-emitting diodes doped with highly emissive bis-cyclometalated iridium(III) complexes” Journal of Organometallic Chemistry, vol. 695 (2010) pp. 1972-1978.) (hereafter “Tsujimoto”) in view of Fukuzaki et al. (US 2011/0049496 A1) (hereafter “Fukuzaki”) set forth in the last Office action as well as the rejections of claims 5-6 under 35 U.S.C. 103 as being unpatentable over Tsujimoto et al. (“Pure red electrophosphorescence from polymer light-emitting diodes doped with highly emissive bis-cyclometalated iridium(III) complexes” Journal of Organometallic Chemistry, vol. 695 (2010) pp. 1972-1978.) (hereafter “Tsujimoto”) in view of Fukuzaki et al. (US 2011/0049496 A1) (hereafter “Fukuzaki”), and further in view of Li et al. (US 2002/0076576 A1) (hereafter “Li”) set forth in the last Office action have been fully considered but they are not persuasive.
Applicant argues that the claimed subject matter possesses unexpected results showing nonobviousness over the cited prior art. Specifically, Applicant argues that the claimed subject matter possesses lower sublimation temperature and lower turn on voltage.
However, there are multiple differences between the cited compound of Tsujimoto and both of the comparative examples and inventive examples of the instant specification. Therefore it cannot be determined what differences result in the improved properties described by Applicant. Therefore it cannot be determined that the claimed subject matter possesses unexpected results.
Additionally the cited prior art teaches that the modifications of the rejection would result in different improved properties. Applicant has not explained that the observed improved properties have a significance equal to or greater than the expected properties based on the cited prior art. See MPEP 716.02(c).
Applicant’s arguments with respect to the provisional rejection of claims 1-13 on the ground of nonstatutory double patenting as being unpatentable over claim 8 of copending Application No. 17/928,808 (reference application) 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.
Applicant’s arguments with respect to the provisional rejection of claims 1-7 and 10-12 on the ground of nonstatutory double patenting as being unpatentable over claim 11 of copending Application No. 18/038,672 (reference application) set forth in the last Office action 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.
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.
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.
Claim(s) 3-4, 6, 8-12, 16, and 21-22 are rejected under 35 U.S.C. 103 as being unpatentable over Tsujimoto et al. (“Pure red electrophosphorescence from polymer light-emitting diodes doped with highly emissive bis-cyclometalated iridium(III) complexes” Journal of Organometallic Chemistry, vol. 695 (2010) pp. 1972-1978.) (hereafter “Tsujimoto”) in view of Fukuzaki et al. (US 2011/0049496 A1) (hereafter “Fukuzaki”) and Kim et al. (WO 2019/221484 A1—machine translation relied upon) (hereafter “Kim”).
Regarding claims 3-4, 8-12, 16, and 21-22: Tsujimoto discloses an organic light-emitting devices comprising the compound shown below as the phosphorescent dopant of the light-emitting layer in a host material {(p. 1975, 2nd col., 2nd to final paragraph to p. 1976, 2nd col., 1st paragraph: The light emitting layer of the organic light-emitting device comprises Compound 3 and PVCz as a host material.), (Scheme 1: Compound 3)}.
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Tsujimoto does not teach that the isoquinoline rings are substituted with a cycloalkyl group.
Fukuzaki teaches a phosphorescent metal complex having the structure of Fukuzaki’s formula (1) for use in an organic electroluminescent device {paragraphs [0066]-[0070]; the compound represented by Fukuzaki’s formula (1) is the phosphorescent material.}. The metal complex comprises a branched alkyl group substituent that is sterically bulky {paragraphs [0068]-[0070]}. The sterically bulky branched alkyl group provides spatial separation between the metal complexes, reducing dimerization reactions between metal complexes, prolonging device lifetime of a device using the compound {paragraph [0068]}. The sterically bulky branched alkyl group also increases the dispersibility of the compounds in the light emitting layer, increasing the efficiency of a device using the compound {paragraph [0069]}. The sterically bulky branched alkyl group also increases the solubility of the compound {paragraph [0070]}.
The compound having the structure of Fukuzaki's formula (1) is substituted by Fukuzaki’s group S11, which is a sterically bulky branched alkyl group {(p. 9, formula (1)), (paragraph [0071]; S11 is represented by Fukuzaki’s structures (a) to (w)), (p. 10, structures (a) to (w))}. S11 can be
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{(paragraph [0071]; S11 is represented by Fukuzaki’s structures (a) to (w)), (p. 10, structures (a) to (w))}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to modify the compound of Tsujimoto by substituting
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onto the compound, based on the teaching of Fukuzaki. The motivation for doing so would have been to provide a sterically bulky group that provides increase dispersibility of the metal complexes, improving lifetime and efficiency of a device using the compound, as well as increasing the solubility of the compound, as taught by Fukuzaki. Furthermore, it would have been obvious to have placed the substituent on the isoquinoline rings of the metal complex, because the positions on the isoquinoline rings would represent a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of substituent and substituent positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
Tsujimoto as modified by Fukuzaki does not teach that the instant R4 is alkyl.
Kim teaches Ir complexes for use as the light emitting dopant of the emissive layer of an organic light emitting device {paragraphs [0006]-[0007], [0016]-[0017], [0140]-[0143], [0161], and [0539]-[0547]}.
The compounds of Kim comprise ligands that are similar to the compounds of the instant claims in that they comprise dibenzofuran or dibenzothiophene structures that are linked to a six-membered ring comprising a single N atom that in turn is coordinated to the Ir metal center, as shown below {paragraphs [0403] and [0423]}.
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Kim teaches that devices utilizing the compounds shown above as emissive dopants have longer lifetimes and higher efficiency than devices using similar compounds differing only in the lack of the isopropyl group substitution {paragraphs [0539]-[0565] and Table 1}.
Given the structural similarity of the ligands comprising the dibenzofuran moiety, it would be expected that a similar improvement would be observed in the compounds of Tsujimoto.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the compound of Tsujimoto such that the substituent at the position equivalent to the instant R4 was isopropyl, based on the teaching of Kim. The motivation for doing so would have been to provide a device having improved lifetime and improved efficiency, based on the teaching of Kim.
Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over Tsujimoto et al. (“Pure red electrophosphorescence from polymer light-emitting diodes doped with highly emissive bis-cyclometalated iridium(III) complexes” Journal of Organometallic Chemistry, vol. 695 (2010) pp. 1972-1978.) (hereafter “Tsujimoto”) in view of Fukuzaki et al. (US 2011/0049496 A1) (hereafter “Fukuzaki”) and Kim et al. (WO 2019/221484 A1—machine translation relied upon) (hereafter “Kim”) as applied to claim 3 above, and as evidenced by m-w.com (www.m-w.com definition of “adjacent”, see attached screenshot) (hereafter “m-w.com”).
Regarding claim 6: Tsujimoto as modified by Fukuzaki and Kim teaches all of the features with respect to claim 3, as outlined above.
m-w.com defines “adjacent” as being “not distant: nearby” as described in the attached screenshot.
There are two positions on the compound of Tsujimoto that can be equated with the instant R4. Either position can be described as being “not distant: nearby” to a metal Ir-C bond. While the teachings place the isopropyl substituent meta to the Ir-C bond, both the positions that are meta and ortho to the Ir-C bond can be accurately described as being “not distant: nearby”.
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 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).
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 nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
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.
Claims 3-4, 6, and 8-13 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 8 of copending Application No. 17/928,908 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding claims 3-4, 6, and 8-13: Claim 8 of copending Application No. 17/928,808 discloses the compound shown below {p. 102}.
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This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
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/DYLAN C KERSHNER/Primary Examiner, Art Unit 1786