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 .
Priority
Acknowledgment is made of applicant’s claim for foreign priority based on applications filed in Korea on October 25, 2021. It is noted, however, that the foreign priority date is the effective filing date of the claimed invention if
The foreign application supports the claimed invention under 112(a), and
The applicant has perfected the right of priority by providing
A certified copy of the priority application, and
A translation of the priority application (if not in English).
In the instant case, the applicant has submitted a certified copy of the priority application, but it is not in English, and the examiner cannot determine if it supports the claimed invention. The effective filing date of the application is considered to be October 24, 2022, which is the actual filing date of instant application 18/049,019.
Specification
The disclosure is objected to because of the following informalities: the specification includes blurry compounds and text in the reaction scheme labelled "Synthesis Example 2: Synthesis of Compound 2" (Pg 62, [00179]).
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Appropriate correction is required.
Claim Rejections - 35 USC § 103
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.
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 Yi et al. (US 2021/0288268 A1 hereinafter "Yi"). It is noted that Yi is cited on the IDS of 06/02/2023.
Regarding instant claim 1, Yi teaches an organometallic complex with transition metal M where L2 may be represented by formula 3-1(65) featuring a pyridine-containing heterocyclic ligand shown below (Pg 113, claim 14).
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In general formula 3-1(65), Z1 and Z2 are defined same as R21 in claim 1 including hydrogen, -Si(Q3)(Q4)(Q5), and -Ge(Q3)(Q4)(Q5). X41 is defined as O, S, N, C, or Si. Yi also teaches L1 of the above organometallic complex as being represented by generic Formula 2A in claim 1 (Pg), which is further defined in claim 10 (Pg 100) where:
1. CY1 and CY2 is 2A(1) and
2. CY21 is CY21(1) shown below.
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In preferred embodiments of Formula 2A, Ra, Rb, R1 to R3, and R21 are each independently -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3) (Pg 1, [0022] and Pg 90, claim 1).
Yi discloses specific examples of the iridium complex with an L1 represented by 2A(1) and CY21(1) in general Formula 2A and with an L2 ligand represented by Formula 3-1(65) including Compound 6 shown below (Pg 114, claim 15).
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Yi does not specifically disclose an iridium complex that meets the claimed Formula 1A and 1B in instant claim 1. Compound 6 shown above differs from the claimed compound in instant claim 1 in that there is not “at least one” substitution of -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3) on either L1 or L2 ligands. However, Yi teaches that Si and Ge are substitutions in preferred embodiments of the compound. Furthermore, Yi teaches Compounds 1, 5, and 7 featuring an ancillary L2 ligand as 2-hydroxyphenyl benzimidazole and a cyclometalated L1 ligand containing an ortho aryl-substituted pyridine shown below (Pg 114, claim 15).
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Yi teaches electron donating alkyl and silyl substitution patterns on the pyridine ring for the L1 ligand on Ir complexes featuring the 2-hydroxyphenyl benzimidazole ancillary ligand. Specifically, Yi teaches a 5-trimethylsilyl or “TMS” substituted pyridine, corresponding to position R12 in instant Formula 1A, offering a low driving voltage and high max external quantum efficiency as shown in Table 3 below.
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Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the 5-position hydrogen, with a TMS group, of the pyridine in general formula 3-1(65) as the L1 ligand in Compound 6. The motivation for doing so would have been to improve the max EQE and lower the driving voltage as taught by Yi. The burden of proof is now shifted to applicants to show otherwise unexpected results.
Further, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to specifically select the TMS and GMS moieties as substitution on other sites of the general formula 3-1(65), such as positions corresponding to R11 to R14 in instant Formula 1A of instant claim 1, which would have been a choice from a finite number of identified, predictable solutions of the L1 cyclometalated ligand for use in a metal complex in the emissive layer of an organic electroluminescent device and possessing the benefits taught by Yi. One of ordinary skill in the art would have been motivated to produce additional compounds comprising the TMS or GMS substituted ligands having the benefits of low driving voltage and high max EQE, as taught by Yi, in order to pursue the known options within their technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified compound of Yi meets the compound of instant claim 2 where the metal center is Ir. For example, the above modified compound of Yi is a compound of the claimed Formula 1A and 1B wherein:
M1 is Ir;
Ln1 is Formula 1A;
Ln2 is Formula 1B;
n1 is 2 and n2 is 1;
ring CY3 is a 5-membered N-containing heterocylic group condensed with a C6 carbocyclic group (benzimidazole);
ring CY4 is a 6-membered carbocyclic group (phenylene);
Y1 is O;
Y2 is O;
At least one of R1, R2, R11-R14, R21 to R26, R30 and R40 (namely R12) is -Si(Q1)(Q2)(Q3) where Q1, Q2, and Q3 are Me (Si(Me)3 or “TMS”); and
R1, R2, R11, R13, R14, R21 to R26, R30 and R40 are each hydrogen.
Regarding instant claim 3, the above modified compound of Yi is a compound of claim 3 where the sum of n1 and n2, 2+1 respectively, is 3.
Regarding instant claim 4, the modified compound of Yi is a compound of claim 4 where CY3 is a benzimidazole group.
Regarding instant claim 5, the above modified compound of Yi is a compound of claim 5 where Y1 is O and Y2 is O.
Regarding instant claim 6, the above modified compound of Yi is a compound of claim 6 where Ln1 includes -Si(Q1)(Q2)(Q3) where Q1, Q2, and Q3 are Me (Si(Me)3 or “TMS”).
Regarding instant claim 7, the above modified compound of Yi is a compound of claim 7 where at least one of R11 to R14, namely R12, is -Si(Q1)(Q2)(Q3) where Q1, Q2, and Q3 are Me (Si(Me)3 or “TMS”).
Regarding instant claim 8, the above modified compound of Yi is a compound of claim 8 where R11 is -Si(Q1)(Q2)(Q3) where Q1, Q2, and Q3 are Me (Si(Me)3 or “TMS”).
Regarding instant claim 9, the above modified compound of Yi is a compound of claim 9 where Ln2 is represented by Formula 1B-2 wherein:
X31 is C and X32 is C;
X33 is N(R33) where R33 is Me;
X35 to X38 is C(H);
X41 to X44 is C(H); and
* and *’ is a binding site to Ir.
Regarding instant claim 10, the above modified compound of Yi is a compound of claim 10 where Formula 1B is represented by Formula 3-5 wherein R35 to R38 are H and R33 is Me.
Regarding instant claim 11, the above modified compound of Yi is a compound of claim 11 where R11 to R14 are each independently H or -Si(Q1)(Q2)(Q3) and R30 and R40 are each independently H. Yi also teaches preferred embodiments of Z1 in general formula 3-1(65), which are defined same as R21 in claim 1 (Pg 6-7, [0081]). Z1 in the general formula of Yi corresponds with R11 to R14 of instant claim 11. Yi teaches the identity of Z1 includes groups represented in instant claim 11 such as, but not limited to:
groups 9-1 to 9-39,
groups 10-1 to 10-44, and
groups 10-201 to 10-272.
Regarding instant claim 12, the above modified compound of Yi does not meet the claimed compound of claim 12. For example, the modified compound does not feature at least one of R11 to R14 is a methyl, an ethyl group, etc. However, Yi teaches that Compounds 1, 5, and 7 featuring an ancillary L2 ligand as 2-hydroxyphenyl benzimidazole and a cyclometalated L1 ligand containing an ortho aryl-substituted pyridine (Pg 114, claim 15). Yi teaches alkyl substitution patterns, such as isobutyl and tert-butyl at the 4-pyridyl position, for the L1 ligand on Ir complexes offering a low driving voltage and higher max external quantum efficiency as shown in Table 3.
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute an isobutyl or tert-butyl group at the 4-pyridyl position, along with the aforementioned TMS group at the 5-pyridyl position, of the pyridine in general formula 3-1(65) as the L1 ligand in Compound 6. The motivation for doing so would have been to improve the max EQE and lower the driving voltage as taught by Yi. The burden of proof is now shifted to applicants to show otherwise unexpected results.
Regarding instant claim 13 and 14, the above modified compound of Yi is a is represented by Formula 30-2 and is electrically neutral.
Regarding instant claim 15, the above modified compound of Yi featuring the TMS group at the 5-pyridyl position reads on compound 33. The above modified compound of Yi featuring the isobutyl group at the 4-pyridyl position and the TMS at the 5-pyridyl position reads on compound 35.
Regarding instant claims 16-20, Yi teaches an organic light-emitting compound wherein the first electrode is an anode, the second electrode is a cathode, the organic layer is between the first electrode and the second electrode wherein the organic layer comprises an emission layer containing the modified compound of Yi (Pg 114, claims 16-18). Yi teaches an electronic apparatus comprising the organic light-emitting device where the emission layer further comprises a host and the amount of host is greater than the amount of the organometallic compound (Pg 115, claims 19-20).
Claims 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2020/0287143 A1, hereinafter "Kim") in view of Ordonez et al. (ES 2642114 A1, hereinafter "Ordonez"). Note that a machine-generated English translation of Ordonez is provided with this office action.
Regarding claims 1-15, Kim teaches, in the field of organic light emitting devices, an iridium complex represented by general formula “Chemical Formula 1” where R1 is -Si(Ra)(Rb)(Rc) and R2 to R4 may be various alkyl groups (Pg 1, ¶ [0008] and Pg 220, claim 1). Kim teaches that a compound of Chemical Formula 1 can be used in the organic material layer of an organic light emitting device where the compound improves the efficiency, achieve low driving voltage, and improve lifetime characteristics (Pg 1, ¶ [0016]). Kim discloses specific examples of the iridium complex represented by Chemical Formula 1 including the compound shown below referred hereinafter as Compound A (Pg 83, second row).
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Compound A of Kim is a compound of Chemical Formula 1 where R1 is trimethylsilane or “TMS” and R2 is isopropyl at the 4-pyridyl position of the pyridine. Kim teaches that the addition of the TMS group to various positions of the dibenzofuran leads to an improvement in the efficiency, lifetime, and a reduction in voltage when compared to examples without the TMS group such as Ir(ppy)3 and compound E3 (Pg 219-220, Table 2).
Kim does not specifically disclose an iridium complex that meets the claimed Formula 1. Compound A shown above differs from the claimed compound in that the phenylpyridine ligand of Compound A is not a group corresponding to the claimed Formula 1 ligand represented by the instant Formula 1B.
Ordonez teaches in the pertinent art of photodynamic therapy and electroluminescent devices an Ir(III) complex with the General Formula of [Ir(C^N)2(N^O)] where (C^N) is a cyclometalated ligand and (N^O) is an arylazole ligand that may be represented by the General Formula shown below (Description and Technical Sector). Ordonez teaches in the General Formula that X can be N-H or N-Me and Y can be O (claim 2). Ordonez discloses specific examples of the iridium complex represented by the General Formula [Ir(C^N)2(N^O)] where the cyclometalated ligand is a phenylpyridine and the arylazole ligand is a hydroxyphenyl benzimidazole shown below, referred hereinafter as Compound of Claim 22 (claim 22).
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Ordonez teaches that the (N^O) ligands, such as the one found in Compound of Claim 22, display excellent phosphorescence intensity and quantum yields while improving emission times and the efficiency of absorbed energy. (Description, pg 3).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the phenylpyridine ligand of Compound A, as taught by Kim, and to select the (N^O) ligand as of Compound 22, as taught by Ordonez. The motivation for doing so would have been to improve efficiency, lifetime, and a reduction in voltage, as taught by Kim, and to improve emission times and the efficiency of absorbed energy, as taught by Ordonez.
Further, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to specifically select the ligand where X is N-Me because it would have been choosing from the list of specifically disclosed identities for X, which would have been a choice from a finite number of identified, predictable solutions of an arylazole ligand (N^O) for use in a metal complex in the emissive layer of an organic electroluminescent device and possessing the benefits taught by Ordonez. One of ordinary skill in the art would have been motivated to produce additional compounds comprising arylazole (N^O) ligands represented by General Formula of Ordonez having the benefits taught by Ordonez in order to pursue the known options within their technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E). The modified compound of Kim in view of Ordonez is shown below.
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The organic light emitting device comprising modified compound of Kim in view of Ordonez meets claims 1-15.
For example, the above Modified Compound of Kim in view of Ordonez is a compound of the claimed instant Formula 1 wherein:
M1 is Ir;
Ln1 is Formula 1A;
Ln2 is Formula 1B;
n1 is 2 and n2 is 1;
ring CY3 is a 5-membered N-containing heterocylic group condensed with a C6 carbocyclic group (benzimidazole);
ring CY4 is a 6-membered carbocyclic group (phenylene);
Y1 is O;
Y2 is O;
At least one of R1, R2, R11-R14, R21 to R26, R30 and R40 (namely R22) is -Si(Q1)(Q2)(Q3) where Q1, Q2, and Q3 are Me (Si(Me)3 or “TMS”);
R1, R2, R11, R14, R21 to R26, R30 and R40 are each independently hydrogen and R13 is alkyl (such as isopropyl or cyclohexyl);
Ln2 is represented by Formula 1B-2;
X33 is N(R33);
N(R33) is methyl; and
CY3 is represented by Formulae 3-5.
The Modified Compound of Kim in view of Ordonez teaches compound 1 of instant claim 15 as discussed above.
Regarding claims 16-20, Kim in view of Ordonez teaches an organic light emitting device comprising a first electrode, a second electrode, and an organic layer disposed between the first and second electrode wherein one or more layers of the organic material layers include an organometallic compound of claim 1 met by the Modified Compound of Kim in view of Ordonez (Kim, claim 9). Further, Kim teaches the organic material layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer (Pg 1, [0004]). Kim teaches that the light emitting layer can include a host (Pg 193, [0059]). Kim teaches a device wherein the emission layer comprises hosts H1 and H2 and an organometallic compound where the weight ratio is 44:44:12; thus, the amount of host is greater than the amount of the organometallic compound (Pg 217, [0241]).
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure includes Shi et al. (US 5,755,999).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LUCAS Q NGUYEN whose telephone number is (571)272-1199. The examiner can normally be reached Monday - Thursday 7:30 am - 5:00 pm Fridays 7:45 am to 12:00PM.
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/L.Q.N./Examiner, Art Unit 1786