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
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.
Claims 1-14, and 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Yen et al. (US 2020/0235318A1, hereinafter "Yen").
Regarding claims 1-14 and 16-20, Yen teaches an organic electroluminescent device comprising a cathode, an anode, and a light emitting layer between the pair of electrodes (claimg 7-11, and pg 2, ¶ [0011]-[0014]). The organic layer comprises an iridium complex represented by Yen’s formula (1) shown below. In Yen’s formula (1), Ar represents a substituted or unsubstituted fused ring hydrocarbon unit and X represents either O or S. B-C represents a bidentate ligand.
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Yen teaches that the compounds having the structure of Yen’s formula (1) may also follow the more specific structure of Yen’s general formula (3) shown above ([0009]) where P may represent a substituted or unsubstituted fused ring hydrocarbon unit having three rings ([0010]). In preferred embodiments, the bidentate ligand of Yen represented by B-C may be an aryl-pyridine ([0018]).
Yen teaches a compound of Yen’s general formula (3) having the structure shown below as compound EX84 featuring an aryl pyridine ligand with a ligand featuring a methyl imidazole substituted with a fused pentacycle (pg 16, 58). Therefore, a ligand where A is methyl imidazole, X is O, and P is anthracene is a known ligand for Yen’s general formula (3). In addition, a bidentate ligand where B-C is a substituted naphthyl pyridine is a known ligand.
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Yen further teaches compound EX7 comprising a bidentate ligand featuring a substituted pyridine fused with a benzene ring or “quinoline” attached to a benzofuran-containing pentacycle fused non-linearly (pg 5, 46). Moreover, one of the rings displays two carbons, that do not participate in ring fusion, as saturated or CH2. Therefore, a ligand where X is O, and P is a 9-10-dihydrophenanthrene is a known ligand for Yen’s general formula (3).
Yen teaches that preferred embodiments of general formula (3) may be configured such that m=1 and 3-m=2. For example, Yen teaches the compounds EX21 and EX24, both displaying an aryl pyridine bidentate ligand where 3-m=2 (pg 7). Therefore, bidentate aryl pyridine ligands where 3-m=2 is a known and acceptable B-C ligand in Yen’s general formula (3).
Further, Yen teaches that ligands similar to EX7 and EX9 exhibit better performance than the prior art organic EL materials by showing a half-life longer than 710 hours at a current efficiency greater than about 19 cd/A (pg 43, Table 1, [0108]-[0108]). For example, compound EX26 (pg 7, 39, 49) is a compound of Yen’s general formula (3) where X is O and P is a fused tetracycle with one saturated carbon. In addition, compound EX68 (pg 14, 40, 55) is a compound of Yen’s general formula (3) where X is O and P is a fused tetracycle featuring two saturated carbons.
While Yen teaches all of the above, Yen does not exemplify a compound having the structure of the instant Formula 1. Yen teaches a ligand where the group corresponding to instant CY41 is 9,10-dihydrophenanthrene and anthracene but not 9,10-dihydroanthracene. 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 have selected 9,10-dihydroanthracene as the group corresponding to instant CY41, based on the teaching of Yen. The motivation for doing so would have been to increase the half-life, lower the driving voltage, and increase the current efficiency as taught by Yen.
Furthermore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select 9,10-dihydroanthracene as the group of instant CY41, because it would have been a combination of prior art elements according to known methods to yield predictable results of a compound useful as the dopant in the light emitting layer of the device of Yen and possessing the benefits taught by Yen. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Yen’s general formula (3) comprising compounds having the benefits taught by Yen in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(A).
Given the general formula and teachings of Yen, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of Yen’s EX7 ligand featuring the 9,10-dihydrophenanthrene moiety wherein the terminal phenyl ring is linear forming a 9,10-dihydroanthracene moiety as the identity of P in general formula (3). One of ordinary skill in the pertinent art would have been motivated to produce the positional isomers of the compound EX7 of Yen represented by general formula (3) in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as dopant in the light emitting layer of the device of Yen and possess the properties taught by Yen. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP 2144.09 II.
The resulting compound, hereinafter referred to as “Modified Compound of Yen,” has the structure shown below and is a compound of Yen’s general formula (3) where ring A is methyl imidazole, ring P is 9,10-dihydroanthracene, and B-C is an ortho-substituted naphthyl-pyridine containing a pyridine substitution.
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The Modified Compound of Yen is a compound of the claimed Formula 1 wherein:
M1 is the transition metal Ir;
Ln1 is a ligand represented by Formula 1A wherein;
ring CY1 is a pyridine group and X1 is N;
ring CY2 is a napthyl group and X2 is C;
the carbocyclic group is substituted with pyridine;
Ln1 is represented by Formula 1A-9 wherein;
R10 is H;
b56 is 4;
Ln2 is a ligand represented by Formula 1B-3 wherein;
X31 and X32 are C;
X41 and X42 are C;
L1 is a single bond and R7 is methyl;
Y4 is O;
Y41 and Y42 are CH2;
L1 is a single bond;
R7 is methyl
N1 is 2;
N2 is 1;
the organometallic compound is represented by Formula 30-3;
the sum of n1 and n2 is 3 and;
the organometallic compound is electrically neutral.
Therefore, the Modified Compound of Yen meets instant claims 1-4 and 6-14.
The Modified Compound of Yen is represented by instant Formula 1A-9 where X11 to X14, X23, and X24 are CH. X21 and X23 are each independently C(R) as described in connection to R20 in instant claim 1 where the neighboring two are bonded together to form a substituted C6 carbocyclic group where the unit, as a whole, is referred to as “naphthalene.” R20 is pyridine and b52 is 1. Therefore, the Modified Compound of Yen meets instant claim 5.
Yen teaches that the compound of general formula (1) may be used in an organic electroluminescent device ([0011]- [0014]). The device comprises a pair of electrodes having a cathode and anode where the light emitting layer and organic thin film layers are between the electrodes. Yen further teaches a compound of general formula (1) may be used as a dopant material in the light emitting layer.
Regarding claims 16 – 20, Yen teaches the light emitting layer comprises a host and an emitting guest material or “dopant” where the amount of host material may be doped at around 15%; thus, the amount of host is greater than the amount of organometallic compound (pg 2, ¶ [0011]-[0014]). Yen further teaches that organic thin film layers can include a hole transport layer, hole blocking layer, an electron transport layer, an electron blocking layer, and a hole transporting layer (pg 1, ¶ [0004]-[0006]).
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Yen et al. (US 2020/0235318A1), and further in view of Ma et al. (CN 111253440, hereinafter "Ma '440"), Karatsu et al. (Inorg. Chem. 2013, 52, 12338−12350, hereinafter "Karatsu"), and Ma et al. (US 2013/0181190A1, hereinafter "Ma '190"). Note that a machine-generated translation of Ma ‘440 is
provided with this office action.
Regarding claim 15, the Modified Compound of Yen meets the limitations of instant Formula 1 of instant claim 1 above. Yen further teaches that the B-C ligand of general formula (3) may be phenyl pyridine ([0018]). Yen teaches, in preferred embodiments, compound EX13 shown below of general formula (1) comprising of a B-C ligand that is phenyl pyridine (pg 5). Therefore, phenyl pyridine is a known ligand for B-C for the general formula (3) of Yen.
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Yen teaches compound EX9 (pg 5), shown above, which is a compound of general formula (3) where P is a fused three-membered ring arranged linearly.
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 have selected phenyl pyridine as the B-C ligand and the linear arrangement of 9,10-dihydroanthracene as P in general formula (3) of Yen, based on the teaching of Yen. The motivation for doing so would have been to increase the half-life, lower the driving voltage, and increase the current efficiency as taught by Yen.
Furthermore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select 9,10-dihydroanthracene in the linear orientation of P in general formula (3) of Yen, because it would have been a combination of prior art elements according to known methods to yield predictable results of a compound useful as the dopant in the light emitting layer of the device of Yen and possessing the benefits taught by Yen. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Yen’s general formula (3) comprising compounds having the benefits taught by Yen in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(A).
The modified compound of Yen is shown below and will be referred hereinafter as “Intermediate 1 of Yen”.
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Intermediate 1 of Yen is a compound of Applicant’s Formula 30-2 in instant claim 13 where Y41 and Y42 is CH2. However, Intermediate 1 of Yen fails to read on the limitations of Applicant’s Compound 31 of instant claim 15 shown below. Applicant’s Compound 31 is a compound of Formula 30-5 where:
X33 to X36 are CH forming a “benzimidazole”;
Y41 is O and Y42 is C(CH3)2 wherein;
CY41 in instant Formula 1B is “dimethylxanthene”;
L1 is a single bond and;
R7 is a “diisopropylbiphenyl.”
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Ma ‘440 teaches, in the analogous art of organic light-emitting materials, Compound 1 of Ma ‘440 comprising of a heteroleptic iridium complex featuring phenyl pyridine ligands with a fused substitution shown below. Ma ‘440 teaches that “dimethylxanthene” is a substitution for an aryl group in an organometallic ligand featuring an imidazole. Ma ‘440 further teaches that organometallic complexes containing “dimethylxanthene” exhibit low drive voltage, high efficiency, and a long lifespan (Description, Table 2). Therefore, the dimethylxanthene” unit is a known and acceptable substitution for an aryl group for an heteroleptic iridium ligand containing an imidazole.
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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 have selected “dimethylxanthene” of Ma ‘440 as the aryl group P of the Intermediate 1 of Yen. The skilled artisan would have been motivated to combine Yen with Ma ‘440 in order to achieve a device with low drive voltage, high efficiency, and a long lifespan as taught by Ma ‘440. The resulting modified complex is shown below and referred to hereinafter as “Intermediate II of Yen and Ma’440.”
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The combination of Yen and Ma ‘440 fails to teach a motivation for modifying ring P separately from ring A in general formula (3) of Yen.
Karatsu teaches in the analogous art of light-emitting organic materials that the HOMO of an iridium phenyl pyridine complex is “mainly localized at the iridium d-orbital and phenyl moiety, and the LUMO is localized at the pyridyl moiety” (pg 12338, col II). Karatsu further teaches a strategy to stabilize the HOMO with the introduction of electron withdrawing groups on the aryl ring resulting in a compound with high efficiency emission (pg 12339, col I).
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 have selected the “dimethylxanthene” of Ma ‘440 over “dihydroanthracene” as an electron withdrawing moiety through the more electronegative oxygen atom in the aryl unit. The skilled artisan would have been motivated to combine Yen and Ma ‘440 with Karatsu to achieve a compound with a stabilized aryl HOMO, thereby achieving higher emission efficiency. The combination of Yen, Ma ‘440, and Karatsu would have provided motivation towards the Intermediate II of Yen and Ma ‘440 shown above.
The combination of Yen, Ma ‘440, and Karatsu fails to teach the limitations of a “benzimidazole” substituted with a “diisopropylbiphenyl” of Applicant’s Compound 31 in instant claim 15.
Ma ‘190 teaches, in the analogous art of organic light-emitting materials, compound 6-X where X can be O or S shown below (pg 8). Ma ‘190 teaches that a heteroleptic iridium complex comprising of a phenyl pyridine ligand may contain a third ligand where a dibenzofuran is substituted with a “benzimidazole” and a “diisopropylbiphenyl” specifically.
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Ma ‘190 further teaches that compounds containing similar moieties display a high external quantum efficiency, luminous efficiency, and power efficiency (pg 14, Table 2).
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 have modified Intermediate II by selecting the benzimidazole and diisopropylbiphenyl of Ma ‘190 as ring A of general formula (3) of Yen. The skilled artisan would have been motivated to combine Yen, Ma ‘440, and Karatsu with Ma ‘190 to achieve an organometallic compound with a high external quantum efficiency, luminous efficiency, and power efficiency as taught by Ma ‘190. The resulting modified compound is shown below and referred hereinafter as “Modified Compound II of Yen, Karatsu, Ma’440, and Ma ‘190”. Therefore, the Modified Compound II of Yen, Karatsu, Ma’440, and Ma ‘190 reads on Applicant’s Compound 31 of instant claim 15.
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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
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786