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 EP on July 27, 2022. It is noted, however, that the
foreign priority date is the effective filing date of the claimed invention if
a. The foreign application supports the claimed invention under 112(a), and
b. The applicant has perfected the right of priority by providing
i. A certified copy of the priority application, and
ii. A translation of the priority application (if not in English).
In the instant case, the applicant has not submitted a certified English copy of the priority application. The effective filing date of the application is considered to be July 7, 2023, which is the actual filing date of instant application 18/351,857.
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 and 8-14 are rejected under 35 U.S.C. 103 as being unpatentable over Stoessel et al. (WO 2019/158453, hereinafter "Stoessel"). Note that a machine-generated English translation is relied upon and provided with this office action.
In the pertinent art of organic light-emitting devices, Stoessel teaches an iridium complex suitable for use in organic electroluminescent devices following the formula (1) of Stoessel, wherein ligands L1, L2, and L3 are bonded to V, a group of formula (2) of Stoessel, wherein Compound 267 is a compound of formula (1) of Stoessel (abstract, Description pg 1, 47).
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Compound 267 of Stoessel is a compound of Formula (1) of Stoessel and V is represented by Formula (2) of Stoessel wherein:
V1 and V2 are CH2CH2;
L1 and L2 are phenyl-pyridine ligands;
V3 is phenyl;
V3 is a substituted dibenzoxazole-pyridine ligand;
X1 is carbon.
Stoessel does not particularly limit V3 to being phenyl: Stoessel teaches that V3 is equal or different to V1 or V2 (Description pg 1). Stoessel also teaches specific compounds including:
Compounds 19-22 wherein ligand L3 may contain a dibenzofuran structure and the dibenzofuran may be unsubstituted or substituted with a phenyl at any position and the pyridine may be unsubstituted (pg 57);
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Compound 594 wherein ligand L3 may contain a dibenzofuran structure and the dibenzofuran may be substituted with one or more fluorine at any position (pg 137).
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Stoessel teaches the above; however, Stoessel fails to teach a specific compound wherein V3 is CH2CH2, the L3 ligand with pyridine being unsubstituted, and the L3 ligand with dibenzofuran containing a fluorine.
Stoessel teaches that an organic light-emitting device containing the iridium complex of Stoessel’s formula (1) in the organic layer displays an improved external quantum efficiency and a longer LD90 service life (Description pg 206-210, 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 substitute V3 with CH2CH2, the L3 ligand with pyridine being unsubstituted, and the L3 ligand with dibenzofuran containing a fluorine in the compound 267 of Stoessel, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the iridium complex in the organic layer of the light-emitting device of Stoessel and possessing the benefits taught by Stoessel. One of ordinary skill in the art would have been motivated to produce additional compounds represented by substituting V3 with known and acceptable groups having the benefits of an improved external quantum efficiency and a longer LD90 service life taught by Stoessel in order to pursue the known options within his or her technical grasp with a reasonable expectation of success (Description pg 206-210, Table 2). See MPEP 2143.I.(E).
The resulting Modified Compound 1 of Stoessel is shown below wherein the locations marked “*” are bonded to Ir.
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Modified Compound 1 of Stoessel
The Modified Compound 1 of Stoessel wherein “*” indicates binding sites to Ir is a compound of instant formula (1) in instant claim 1 wherein:
The ligand L has a structure of formula (2);
The ligand L has a structure of formula (4);
m, n, o, p, q, and s are 0;
R is F and r is 1 wherein;
The sum of q + r + s is 1 which is <= 4;
R6 and R7 are H.
Therefore, the Modified Compound 1 of Stoessel reads on instant claims 1-2 and 8. Note that instant claim 8 requires Ar as a phenyl group, but allows s to be 0.
The Modified Compound 1 of Stoessel teaches the above, however, it is silent on a phenyl group substitution for the dibenzofuran moiety.
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 L3 ligand with dibenzofuran containing a phenyl group in the Modified Compound 1 of Stoessel, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the iridium complex in the organic layer of the light-emitting device of Stoessel and possessing the benefits taught by Stoessel. One of ordinary skill in the art would have been motivated to produce additional compounds represented by substituting V3 with known and acceptable groups having the benefits of an improved external quantum efficiency and a longer LD90 service life taught by Stoessel in order to pursue the known options within his or her technical grasp with a reasonable expectation of success (Description pg 206-210, Table 2). See MPEP 2143.I.(E).
The resulting Modified Compound 2 of Stoessel is shown below wherein the locations marked “*” are bonded to Ir.
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Modified Compound 2 of Stoessel
The Modified Compound 2 of Stoessel wherein “*” indicates binding sites to Ir is a compound of instant formula (1) in instant claim 1 wherein:
The ligand L has a structure of formula (2);
The ligand L has a structure of formula (4);
The ligand L has a structure of formula (7);
The ligand L has a structure of formula (11b);
m, n, o, p, and q are 0;
Ar is phenyl;
s is 1;
R is F and r is 1 wherein;
The sum of q + r + s is 2 which is <= 4;
R6 and R7 are H.
Therefore, the Modified Compound 2 of Stoessel reads on instant claims 3-5 and 9.
Regarding claim 10, Stoessel teaches a process for preparing the Ir complexes of formula (1) involving reacting tris-acetylacetonato-iridium(III) or iridium(III) chloride, which is an iridium halide, with a free ligand such as L1 (Description pg 175-176, Variant A-C).
Regarding instant claim 11, Stoessel teaches a formulation comprising an Iridium complex of formula (1) and another compound that is selected from a solvent such as DCM in the synthesis of Ir(L1-2Br) (Description pg 197). Note that claim 11 requires at least one further compound selected from a solvent and a matrix material wherein DCM reads on the solvent.
Regarding instant claim 12, Stoessel teaches that an iridium complex of formula (1) is photocatalyst or a photoinitiator (claim 13).
Regarding instant claims 13-14, Stoessel teaches the Modified Compound 1 that reads on claim 1 as described above. Stoessel teaches that a compound of formula (1) may be used in an organic light-emitting device with the structure of substrate/HIL/HTL/emission layer/HBL/ETL/cathode wherein the emission layer consists of one matrix material and an emitting dopant that is the iridium complex of formula (1) (Description pg 205-206, Table 1). Stoessel teaches the above, but fails to teach the Modified Compound 1 being in the organic light-emitting device. Stoessel teaches an anode, a cathode, and an emission layer and the compound of formula (1) is in the organic layer as discussed above. It would have been obvious to use the Modified Compound 1 of Stoessel in the emission layer with the device structure of anode/emission layer/cathode as Stoessel demonstrates this device structure was known prior to the effective filing date of the claimed invention. The resulting device reads on instant claims 13-14.
Claims 5-7 and 15-16 are rejected under 35 U.S.C. 103 as being unpatentable over Stoessel et al. (WO 2019/158453, hereinafter "Stoessel") as applied to claims 1-5 and 8-14 described above in view of Wang et al. (CN114437137, hereinafter "Wang"). Note that a machine-generated English translation is relied upon and provided with this office action.
Stoessel teaches the Modified Compound 2 of Stoessel that reads on claims 1-5 and 8-14 as described above. Stoessel teaches that deuterium is a known and acceptable substitution for H in the formula (1) of Stoessel as seen through compound 670 wherein deuterium is found in V1 and V2 of formula (2) and also found in the modified dibenzofuran structure attached to the pyridine for L3 of formula (1) (pg 146 col II row II).
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Stoessel teaches the above; however, Stoessel is silent on the Modified Compound 1 of Stoessel where a deuterium atom is bonded in all ortho-positions to the fluorine on the dibenzofuran.
In the relevant art of organic light-emitting devices, Wang teaches that an iridium complex with (1) a phenyl-pyridine auxiliary ligand and (2) a ligand containing pyridine and a dibenzofuran moiety may contain a substitution pattern on the dibenzofuran where fluorine has a deuterium atom at all ortho-positions, see below (pg 11 col I row V).
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Wang teaches that an iridium complex with (1) a phenyl-pyridine auxiliary ligand and (2) a ligand containing pyridine and a dibenzofuran moiety may contain a substitution pattern on the dibenzofuran where the fluorine has phenyl group at the ortho position, see below (pg 11 col III row III).
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Wang teaches that the organic light-emitting device containing the iridium complex of Wang has an improved driving voltage, current efficiency and lifespan (Description pg 56, 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 further modify the Modified Compound 1 of Stoessel in the light-emitting device of Stoessel to include a deuterium at the ortho-position of the fluorine atom, based on the teachings of Wang. The motivation for doing so would have been to obtain a device with an improved driving voltage, current efficiency and lifespan, as taught by Wang (Description pg 56, Table 3).
The resulting Modified Compound 3 of Stoessel and Wang is shown below.
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Modified Compound 3 of Stoessel and Wang
The resulting Modified Compound 3 of Stoessel and Wang contains a deuterium ortho to the fluorine atom and reads on instant claim 6 and formula (11b-1) of instant claim 7.
Regarding instant claims 5 and 15-16, the Modified Compound 3 of Stoessel and Wang displays a dibenzofuran moiety that is substituted by a phenyl group, a fluorine atom, and a deuterium atom as described above. Stoessel does not particularly limit the substitution on the dibenzofuran to be only phenyl, fluorine, and deuterium: Stoessel defines R on the dibenzofuran moiety, which is represented by structure CyC-16a, as including a cyclic alkyl group with 3-20 carbon atoms (Description pg 2, 7-9). Stoessel teaches that a ligand L3 that is substituted by a phenyl group may be suitably replaced by a cyclohexyl-group as seen through compound 592 (pg 136 col II row II) and compound 622 (pg 140 col I row II).
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Stoessel teaches the above, however, Stoessel does not teach a specific compound wherein a ligand L3 contains a dibenzofuran moiety that is substituted with a cyclohexyl group.
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 further substitute the phenyl group with a cyclohexyl group in Modified Compound 3 of Stoessel and Wang in the light-emitting device of Stoessel, based on the teachings of Stoessel. The motivation for doing so would have been to obtain a device with an improved external quantum efficiency and a longer LD90 service life as taught by Stoessel (Description pg 206-210, Table 2).
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 phenyl group with a cyclohexyl group in the Modified Compound 3 of Stoessel and Wang, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the Ir complex of formula (1) in the emissive layer of the light-emitting device of Stoessel and possessing the benefits taught by Stoessel. One of ordinary skill in the art would have been motivated to produce additional compounds represented by the iridium complex of formula (1) having the benefits taught of an improved external quantum efficiency and a longer LD90 service life taught by Stoessel in order to pursue the known options within his or her technical grasp with a reasonable expectation of success (Description pg 206-210, Table 2).
The resulting Modified Compound 4 of Stoessel and Wang is shown below featuring a cyclohexyl group on the dibenzofuran moiety.
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Modified Compound 4 of Stoessel and Wang
The Modified Compound 4 of Stoessel and Wang is a compound of formula (11c) in instant claim 5 wherein R5 is cyclohexyl and is also a compound of formula (11c-1) in instant claim 7 wherein R5 is cyclohexyl and, thus, reads on instant claims 5 and 15-16.
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 12:00 pm.
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/L.Q.N./Examiner, Art Unit 1786
/JENNA N CHANDHOK/Primary Examiner, Art Unit 1789
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