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 allowance or after an Office action under Ex Parte Quayle, 25 USPQ 74, 453 O.G. 213 (Comm'r Pat. 1935). 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, prosecution in this application has been reopened pursuant to 37 CFR 1.114. Applicant's submission filed on 3/30/26 has been entered.
According to MPEP 706.07(h), the filing of an RCE “withdraws” the notice of allowance and returns the application to the status of a pending application. However, it does not “undo” previous amendments that were properly entered into the record. This includes the Examiner’s amendment on 12/30/25 because said amendment was authorized by Applicants representative and entered prior to the mailing of the allowance. As such, the claims as amended in the 12/30/25 action are the operative claims. Currently, claims 1 and 4-20 are pending with claim 1 including the subject matter of previously presented claim 2 (which has been canceled via an Examiner’s amendment). Additionally, claims 7, 10, and 14 are dependent on claim 1, not claim 2.
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, 9-12, and 15-20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Adamovich et al. (US 2012/0319146),1 further evidenced by Watanabe et al. (Bull. Chem. Soc. Jpn. 2019, 92, 716-728).
Claim 1: Adamovich et al. teaches fine tuning of emission spectra by the combination of multiple emitter spectra. Table 3 is drawn to a mixture of emitters C and D, whose structures are shown in Figure 19. The mixture of emitters D and C in table 3 have a │lP(Ir1) - lP(Ir2)│of 12 nm (630 nm – 618 nm) with emitter D serving as Ir1 and emitter C serving as Ir2, which satisfies expression 1 of claim 1. Emitters C and D are both iridium complexes which satisfy formula 1 and 2, respectively, of claim 1. As applied to formula 1, emitter C has n11 equal to 2, n12 equal to 1, n13 equal to zero, L11 equal to a bidentate ligand bonded to Ir of Formula 1 via nitrogen atom and a carbon atom, and L12 equal to a bidentate ligand bonded to Ir of Formula 1 via two oxygen atoms. As applied to formula 2, emitter D has n21 equal to 2, n22 equal to 1, n23 equal to zero, L21 equal to a bidentate ligand bonded to Ir of Formula 2 via a nitrogen atom and a carbon atom, and L12 equal to a bidentate ligand bonded to Ir of Formula 2 via two oxygen atoms. Condition 1 of claim 1 requires that when (a) through (g) is satisfied, then ring A1 and ring A5 are different from each other. In emitters C and D, rings A1 and A5 are different from each other (quinoline and isoquinoline rings), which satisfies Condition 1. As such, the mixture of emitters C and D as explicitly taught by Adamovich et al. satisfies formulae 1 and 2 of claim 1.
While Adamovich et al. does not explicitly teach that emitter D (Ir1) has a greater horizontal orientation ratio compared to emitter C (Ir2), a person having ordinary skill in the art would have expected Expression 4 to be satisfied given the evidentiary teachings of Watanabe et al. Watanabe et al. is a comprehensive review of how the alignment of molecules, specifically their horizontal orientation, is a critical factor in enhancing the efficiency of OLEDs. Specifically, when light-emitting molecules are oriented horizontally (parallel to the substrate), the light outcoupling efficiency can be significantly improved (Figure 1). When transition dipole moments of emitter molecules are aligned horizontally, the light they emit is more likely to escape the device, thereby increasing the external quantum efficiency. Watanabe et al. teaches that higher aspect ratio molecules tend to lie flat which increases their horizontal orientation. Figure 5 shows three iridium complexes. As the transition dipole of these molecules increases, so too does the horizontal orientation. It can be seen at the bottom of figure 5 that increasing the horizontal orientation increases the external quantum efficiency. Using the trend shown in Figure 5, one would expect that compound D of Adamovich et al. would have a higher horizontal orientation due to the increase number and size of the alkyl groups (5 alkyl groups vs. 4 alkyl groups, and instead of only 4 methyl groups as in compound C, compound D has two methyl groups, an isopropyl group, and two iso-butyl groups. The alignment of compound D would be expected to be greater, and compound D would be expected to have an increased horizontal dipole ratio. This feature also satisfies Expression 4 of independent claim 1.
Claims 9 and 10: Emitter D has a lP(Ir1) of 630 nm and emitter C has a lP(Ir2) of 618 nm, which are both within the 570-650 nm range of claim 9 and lP(Ir1) is within the 620-650 nm range of claim 10.
Claims 11 and 12: Emitters C and D satisfy the limitations of claims 11 and 12 as described in claim 1 above.
Claim 15: In each of emitters C and D of Adamovich et al., L11 and L12 are different from each other which satisfies condition A, L21 and L22 are different from each other which satisfies condition B, L11 and L21 are different from each other which satisfies condition C, and L12 and L22 are different from each other which satisfies condition D. All conditions A-D of claim 15 are anticipated by emitters C and D of Adamovich et al.
Claim 16: Emitters C and D of Adamovich et al. as taught in figure 19 anticipate the structural limitations of claim 16 with L11 being a ligand of Formula 1-1, L12 being a ligand of Formula 1-3, L13 being absent (n13 is zero), L21 being a ligand of Formula 2-1, L22 being a ligand of Formula 2-3, and L23 being absent (n23 is zero). In formula 1-1, Y1 is N, d1 is 1, W1 is a single bond, e1 is 1, Z1 is methyl, A1 is quinoline, Y2 is C, d2 is 1, W2 is a single bond, e2 is 1, Z2 is methyl, and A2 is benzene. In formula 1-3, Y11 and Y12 are O, R1 and R2 are methyl, and R3 is hydrogen. In formula 2-1, Y5 is N, d5 is 1, W5 is a single bond, e5 is 1, Z1 is isopropyl, A5 is isoquinoline, Y6 is C, d6 is 2, W6 is a single bond, e6 is 1, Z6 is methyl, and A6 is benzene. In formula 2-3, Y13 and Y14 are O, R4 and R5 are sec-butyl, and R6 is hydrogen.
Claim 17-19: Emitters C and D are mixed together and applied as a emissive film/layer in an organic light-emitting device which comprises the customary layers, anode, hole transport region, emission layer comprising emitters C and D (and a host material), an electron transport region, and a cathode (figures 3 and 7). Devices which comprise an emitter mixture of C and D or A and B anticipate the layer and light-emitting device as recited in claims 17-19.
Claim 20: Adamovich et al. further teaches and claims consumer products which comprise the mixed dopant light-emitting devices (claim 11 of Adamovich et al.), which would inherently be an electronic apparatus satisfying claim 20
Allowable Subject Matter
Claims 5-8, 13, and 14 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. The iridium mixture of complexes C and D cannot be relied upon to reject the HOMO energy level requirements of claim 5 as well as the limitations of claims 6-8 and 13-14 which are directed to green and blue emitters.
Claim 4 is allowed, It cannot be stated with any degree of certainty that the combinations of the iridium complexes taught by Adamovich et al. satisfy one of expressions 1-4 and expression 5 as required by independent claim 4.
Comment on the 3/30/26 Information Disclosure Statement
The IDS filed on 3/30/26 includes several references which were cited as part of a European search report. This includes Adamovich et al. (US 2018/0342680). Adamovich et al. teaches embodiments where a mixture of two iridium dopants are employed in an emission layer (claim 6 of Adamovich et al.). However, it cannot be stated with any degree of certainty that the claimed combinations would satisfy expression 1 and at least one of expressions 2-4 as required by independent claim 1, or which satisfies one of expression 1-4 and at least expression 5 as required by independent claim 4. The iridium complexes taught by Tani et al. (WO 2013/161739) and Jung et al. (US 2008/0203360) do not satisfy Condition 1 as recited in independent claims 1 and 4, which requires both complexes to have a ligand which is bonded to the iridium via oxygen atoms.
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
1 This rejection was previously presented without the evidentiary reference of Watanabe et al.