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 1-5, 7-14, 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 1-5, 7-11, 13-14, and 16-20, Yen teaches an organic electroluminescent device comprising a cathode, an anode, and a light emitting layer between the pair of electrodes (claim 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 represented 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) comprises a structure having the 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 a phenyl pyridine ([0018]).
Yen further teaches a compound of Yen’s general formula (3) having the structure shown below as compound EX21 featuring two phenyl pyridine ligands with a third ligand featuring a pyridine with a fused pentacycle (pg 7, 48).
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Yen further teaches two compounds of Yen’s general formula 3 having the structures shown above as compounds EX7 and EX9 (pg 5, 46). Compound EX9 teaches a bidentate ligand featuring a substituted pyridine attached to a benzofuran-containing pentacycle fused linearly. Compound EX7 also teaches a bidentate ligand featuring a substituted pyridine fused with a benzene ring or “quinoline” attached to a benzofuran-containing pentacycle fused non-linearly. Moreover, one of the rings displays two carbons that do not participate in ring fusion as saturated or CH2. Therefore, a ligand where A is a substituted pyridine, X is O, and P is a 9-10-dihydrophenanthrene is a known ligand for Yen’s general formula (3). Further, a ligand where A is a substituted pyridine, X is O, and P is anthracene is also a known ligand for 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.
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 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).
Further, 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. 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 quinoline, ring P is 9,10-dihydroanthracene, and B-C is a 4-methylphenyl ortho-substituted pyridine.
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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 benzene group and X2 is C;
R23 is methyl;
Ln2 is a ligand represented by Formula 1B-2 wherein;
Ring CY3 is a quinoline group;
R41 to R48 are H;
Y41 and Y42 are CH2;
Y4 is O;
N1 is 2;
N2 is 1;
the sum of n1 and n2 is 3 and;
the organometallic compound is electrically neutral.
Therefore, the Modified Compound of Yen meets instant claims 1-5, 7-11, and 13-14.
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) maybe be used as a dopant material in the light emitting layer. 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. Yen further teaches that an 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. Therefore, the Modified Compound of Yen reads on claims 16-20.
Regarding claim 12, the Modified Compound of Yen does not contain substitution at the pyridine ring corresponding to the instant R31 to R34 position of instant Formula 1. However, Yen teaches that a compound of general formula (3) may be substituted with R1 at the corresponding positions at the pyridine ring. For example, Yen teaches compounds EX19 containing a methyl substitution corresponding to the instant R33 position (pg 6). Yen also teaches tert-butyl as a preferred substitution corresponding to the instant R33 position (pg 9).
Claims 5-6 are rejected under 35 U.S.C. 103 as being unpatentable over Yen et al. (US 2020/0235318A1) as applied to claims 1-4 above, and further in view of Tsai et al. (US 2019/0280219A1, hereinafter "Tsai").
Regarding claims 5-6, the Modified Compound of Yen teaches the limitations of claims 1-4 and is a compound of Formula 1 where ligand Ln1 is a ligand represented by Formula 1A. The Modified Compound of Yen also teaches for Formula 1A that CY1 is pyridine and CY2 is benzene, forming the bidentate phenylpyridine ligand. Yen further teaches that the pyridine portion may be substituted with R5 and the benzene portion may be substituted with R6. However, Yen fails to teach the substitution of atoms within either the pyridine or benzene rings with a nitrogen atom. Yen does not teach any of the positions, corresponding to instant X11 to X14 and X21 to X24 in instant Formula 1A-1, (instant claim 5) as independently being a nitrogen atom shown below.
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Tsai teaches in the analogous art of organic electroluminescent devices a heteroleptic organometallic compound comprising a ligand, similar to Yen’s ligand, featuring a pyridine substituted with a benzofuran fused with an anthracene forming a fused pentacycle such as ligand 85 following the Lx10-1 subtype (pg 96). Tsai further teaches ligands, such as LB455 following the LB subtype shown below, suitable to be paired with ligand 85 (claim 48, pg 254).
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Tsai teaches that heteroleptic organometallic complexes of the above type exhibit enhanced device lifetime and a narrow emission spectrum towards the production of commercially useful OLED devices ([0291] and Table 1).
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 ligand LB455 of Tsai with the phenyl pyridine ligand in the Modified Compound of Yen. The motivation for doing so would have been to provide a device with an enhanced lifetime and a narrow emission spectrum as taught by Tsai.
In particular, 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 the compound above because it would have been choosing from a list of exemplified ligands represented by LB and taught by Tsai, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the emissive dopant in the light emitting layer of the device of Yen and possessing the benefits taught by Tsai. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Tsai’s LB having the benefits taught by Tsai in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The compound of Yen modified by the teachings of Tsai reads on claimed Formula 1A-1 wherein:
X12 is N;
X13 is C(R13);
X14 is C(R14);
R13 and R14 are bonded together to form a ring and;
X21 to X24 is C.
The compound of Yen modified by the teachings of Tsai reads on claimed chemical formula 1A-23 where b55 is 2 and R10 is bonded together to form a ring.
Allowable Subject Matter
Claim 15 is 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 following is a statement of reasons for the indication of allowable subject matter:
As per claim 15, the closest prior art is considered to be Yen (US 2020/0235318A1). Claim 15 requires that:
For Formula 30-1:
Y41 is O and;
Y42 is C(Me)2 or O.
For Formula 30-2:
Y41 is O and;
Y42 is C(Me)2 or O.
For Formula 30-3:
Y41 is C(Me)2 or O and;
Y42 is O.
Yen teaches 9-10 dihydroanthracene unit for CY41 in instant Formula 1B where both Y41 and Y42 are C(R)2 which is outside the definitions of claim 15. The prior art as a whole does not teach or suggest a motivation to substitute an oxygen group for a carbon group as required by claim 15.
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached at 571-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/L.Q.N./ Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786