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 .
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 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2022/0165969 A1) in view of Xia et al. (US 2010/0270916 A1) and Teets et al. (Chem. Eur. J. 2019, 25, 6026 – 6037).
Regarding claim 1, Kim teaches an organometallic compound (D-6) used as a dopant in an OLED device (Comparative Example 6, Table 6),
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wherein the claimed Formula 1,
M1 is the transition metal Iridium (Ir)
L1 is a ligand represented by Formula 1A, wherein the claimed Formula 1A,
X1 is N
X2 is C
CY2 is a C6 carbocyclic group
Z1 is an unsubstituted C1 alkyl group
a1 is 1
R1 is hydrogen
b1 is 5
Two R2s are hydrogen and two R2s are an unsubstituted C1 alkyl group
b2 is 4
n1 is 2
n2 is 1
Compound D-6 of Kim differs in the claimed Formula 1 in that:
Z1 does not comprises at least one deuterium
L2 is not a ligand represented by Formula 1B
However, Kim teaches general formula 1
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wherein the substituents may be deuterated (para. [0031] – [0032]).
Xia teaches Iridium complexes with methyl-D3 substitution. Additionally, Xia teaches that deuterium substitution provides many benefits, e.g., increased efficiency and lifetime (para. [0067]). Therefore, compounds comprising a ligand having deuterium substitution may be advantageously used in organic light emitting devices (para. 0067]). Moreover, Xia teaches Compound 26 as a suitable iridium complex with a deuterated ligand.
Compound 26
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of Xia differs from compound D-6 of Kim in that Z1 is a deuterated methyl group instead of a hydrogenated methyl group.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify compound D-6 of Kim, because it would have been choosing a deuterated methyl group for Z1 instead of a hydrogenated methyl group, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the dopant in the emissive layer of the OLED device of Kim and possessing the benefits taught by Xia. One of ordinary skill in the art would have been motivated to produce additional compounds represented by/devices comprising a deuterated ligand for an OLED device having the benefits of increased efficiency and lifetime taught by Xia in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
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The Modified Compound D-6 of Kim reads on Formula 1 of instant application wherein Z1 comprises 3 deuterium atoms. However, it fails to teach wherein L2 is a ligand represented by Formula 1B.
Teets teaches in his work the effect of ancillary ligands on red-emitting Iridium complexes (abstract). Teets teaches that the used of iridium complexes in OLED applications include benefits such as chemical inertness, good thermal and photostability, color tunability and high photoluminescence quantum yields (page 6026, left column, introduction, para. 1). Additionally, Teets teaches that heteroleptic complexes are often cheaper and easier to prepare than homoleptic analogues, while the ancillary ligand can provide a unique channel to change the emission color and have profound impacts on the redox properties and excited-state dynamics (page 6026, introduction, para. 1). Moreover, Teets teaches the use of phenyl isoquinoline in combination with ancillary ligands that show induce significant redshifts of the emission maxima and enhanced phosphorescence quantum yields relative to their corresponding acetylacetonate (acac) analogues or the homoleptic complexes (page 6027, left column, middle to end of para. 1). One of the iridium complexes that Teets teaches is compound 2f,
Teets teaches that compound 2f
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show quantum efficiencies that rival the compounds that have been incorporated into some of the best-performing OLEDs (page 6030, right column end of para. 1). The ancillary ligand of compound 2f is a phenyl isoquinoline ligand paired with a phenyl pyridine ancillary ligand that reads on Formula 1B wherein
R3 and R4 are hydrogen atoms
b3 and b4 are 4
X3 is N
X4 is C
Y1 is O
Therefore, given the teachings of Teets, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the acac ancillary ligand of Kim with the ancillary ligand of Teets, because Teets teaches that ancillary ligands he studied show induce significant redshifts of the emission maxima and enhanced phosphorescence quantum yields relative to their corresponding acetylacetonate (acac) analogues or the homoleptic complexes (page 6027, left column, middle to end of para. 1). The substitution would have been one preferred element for another and one of ordinary skill in the art would reasonably expect the predictable result that the modified compound would be useful as an iridium complex dopant in the emissive layer of the OLED device of Kim and possess the benefits of enhanced quantum efficiencies taught by Teets. See MPEP 2143.I.(B).
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The Further Modified Compound D-6 of Kim reads on the claimed Formula 1 wherein L2 is not a ligand represented by Formula 1B. Additionally, the Further Modified Compound D-6 of Kim reads on compound 1 of claim 14 of instant application. Moving forward, further modified Compound D-6 of Kim will be referred to as Further Modified Compound D-6 of Kim.
Regarding claim 2, modified Kim further teaches wherein M1 is iridium (as defined for Compound D-6 for claim 1, in Paragraph 7).
Regarding claim 3, modified Kim further teaches wherein M1 is Ir, and a sum of n1 and n2 is 3 (as defined for Further Modified Compound D-6 for claim 1, in Paragraph 7, n1=2 and n2=1).
Regarding claim 4, modified Kim further teaches wherein X1 is N, X2 is C, X3 is N, and X4 is C (as defined for Further Modified Compound D-6 for claim 1, in Paragraph 7).
Regarding claim 5, modified Kim further teaches wherein
CY2 and CY4 are a second ring, wherein the second ring is a benzene group
CY3 is a second ring, wherein the second ring is a pyridine group.
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Regarding claim 6, modified Kim further teaches wherein the moiety represented by
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in Formula 1A is a group represented by Formulae 1-4,
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, wherein the claimed Formula 1-4,
Z14 is a substituted C1 alkyl group, wherein the substitution is three deuterium atoms
b11 is 1
Regarding claim 7, modified Kim further teaches wherein the moiety represented by
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in Formula 1A is a group represented by Formulae 2-10,
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, wherein the claimed Formulae 2-10,
X2 is C
R22 and R24 are not hydrogen (methyl groups)
Regarding claim 8, modified Kim further teaches wherein a moiety represented by
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in Formula 1A is a group represented by Formulae 3-1,
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, wherein the claimed Formulae 3-1, X3 is N.
Regarding claim 9, modified Kim further teaches wherein a moiety represented by
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in Formula 1A is a group represented by Formulae 4-1,
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, wherein the claimed Formulae 4-1, X4 is C.
Regarding claim 10, modified Kim further teaches wherein Z1 is -CD3 (as defined for Further Modified Compound D-6 for claim 1 in Paragraph 7).
Regarding claim 11, modified Kim further teaches wherein Z1 is -CD3 (as defined for Further Modified Compound D-6 for claim 1 in Paragraph 7).
Regarding claim 12, modified Kim further teaches wherein R1, two R2s, R3, and R4 are hydrogen, and two R2s are a C1 alkyl group.
Regarding claim 13, modified Kim further teaches wherein the organometallic compound is represented by Formulae 5-4,
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wherein the claimed Formulae 5-4,
M1 is a transition metal (iridium)
n1 is 2
n2 is 1
X1 is N
X2 is C
X3 is N
X4 is C
Y1 is O
Z14 is Z1 and Z1 is a substituted C1 alkyl group, wherein the substitution is three deuterium atoms
R21, R23, R31 to R34, and R41 to R44 are a hydrogen atom
R22 and R24 are an unsubstituted C1 alkyl.
a11 is 0
Regarding claim 14, modified Kim further teaches wherein the Further Modified Compound D-6 is Compound 1 of instant application
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Regarding claim 15, modified Kim further teaches an organic light-emitting device (Comparative Example 6, Table 6), comprising: a first electrode (ITO anode, para. [0110]); a second electrode (Al cathode, para. [0110]); and an organic layer (first and second hole injection layer, first and second hole transport layer, light-emitting layer, electron transport layer, electron injection layer, para. [0110]), arranged between the first electrode and the second electrode, wherein the organic layer comprises and emission layer (light-emitting layer, para. [0110]), and wherein the organic layer further comprises at least one of the organometallic compound of claim 1 (Comparative Example 6, Further Modified Compound D-6, Table 6).
Regarding claim 16, modified Kim further teaches wherein the emission layer (light-emitting layer, para. [0110]) comprises the at least one of the organometallic compound (Comparative Example 6, Further Modified Compound D-6, Table 6).
Regarding claim 17, modified Kim further teaches wherein the emission layer (light-emitting layer, para. [0110]) further comprises a host (Compound B-109, Comparative Example 6, Table 6), and an amount of the host (98 wt% out of the total weight of host and dopant, para. [0110]) in the emission layer is greater than an amount of the at least one of the organometallic compound (2 wt% out of the total weight of host and dopant, para. [0110]) in the emission layer.
Regarding claim 18, modified Kim appears silent with respect to the maximum emission wavelength of Compound D-6. The instant specification recites that Compound 1 (which is equivalent to Compound D-6) has a maximum emission wavelength of 627. Since modified Kim teaches Compound D-6, the same structure as disclosed by the Applicant, the property of having a maximum emission wavelength of about 590 nanometers to about 650 nanometers is considered to be inherent (and would be expected to fall within the range in the claim), absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP 2112.
Regarding claim 19, modified Kim further teaches wherein the first electrode is an anode (ITO anode, para. [0110]), the second electrode is a cathode (Al cathode, para. [0110]), the organic layer further comprises a hole transport region (first and second injection layer and first and second hole transport layer, para. [0110]) arranged between the first electrode and the emission layer, and an electron transport region (electron transport layer, electron injection layer, para. [0110]) arranged between the emission layer and the second electrode, the hole transport region comprises a hole injection layer (first and second hole injection layer, para. [0110]), a hole transport layer (first and second hole transport layer, para. [0110]), an electron transport layer (para. [0110]), an electron injection layer (para. [0110]).
Regarding claim 20, modified Kim further teaches an electronic device (display system or lighting system, para. [0067]), comprising the organic light-emitting device of claim 15.
Conclusions
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/APCV/
Examiner, Art Unit 1789
/JENNA N CHANDHOK/Primary Examiner, Art Unit 1789
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