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 November 8, 2021. 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 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 November 2, 2022, which is the actual filing date of instant
application 18/052,073.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-2 and 10-12 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Beers et al. (US2013/0048963A1, hereinafter "Beers").
Regarding claims 1-2 and 10-12, Beers discloses an organic light emitting device comprising an organic layer disposed between a cathode and anode (pg 30, ¶ [0078]). Beers discloses that “emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present” (¶ [0089]). Beers further discloses a general formula for a platinum (II) organometallic complex, shown below, featuring a tetradentate ligand shown below suitable for use in an organic layer (pg 2). Beers defines rings A, B, and C as each independently a 5- or 6-membered carbocyclic or heterocyclic ring where R3 is optionally fused to B to form a ring.
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Beers further discloses an organometallic complex of General Formula 1 of Beers where ring B features an imidazole where R3 is fused to form a bicyclic structure in Compound 47 shown below (pg 80).
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Compound 47 of Beers is a compound of instant Formula 1-1 wherein:
M is platinum (Pt);
CY1 is phenyl and represented by Formula CY1(1) wherein;
X1 is C;
CY2 is phenyl and represented by Formula CY2(1) wherein;
X2 is C;
CY3 is imidazole wherein;
R3 is C12 carbocyclic group substituted with one R10a wherein;
R10a is C1 alkyl group;
X1 is C, X2 is C, and X3 is N;
X21 is C;
Y1 to Y4 is C;
Y1 and Y2 is connected via single bond;
Y3 and Y4 is connected via double bond;
L1 is single bond;
L2 is CH2;
L3 is single bond;
Therefore, the Compound 47 of Beers meets instant claims 1-2 and 10-12.
Claim Rejections - 35 USC § 102/35 USC § 103
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
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.
Claim 19 is rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Beers et al. (US2013/0048963A1, hereinafter "Beers").
Regarding claim 19, Beers teaches Compound 47 which is a compound of claimed invention instant Formula 1-1 above but does not expressly teach the compound having a triplet metal to ligand charge transfer (3MLCT) value of 10% or more. It is reasonable to presume that the 3MLCT value of 10% is inherent to compound 47. Support for said presumption is found in that the instant specification discloses that embodiments represented by Formula 1-1 may have a 3MLCT value of about 10% or more. Compound 47 is a compound of Formula 1-1 wherein CY1 is phenyl, CY2 is phenyl, CY3 is substituted imidazole, and Y1 and Y2 are connected via single bond, resembling compounds 57 and 65 in instant claim 20. Furthermore, the instant specification discloses that calculated values of 3MLCT for instant compounds 51 and 52 are above 10% which shares a CY1 phenyl ring, CY2 phenyl ring, and CY3 nitrogen-containing heteroaromatic ring in common with Compound 47 of Beers. Therefore Compound 47 of Beers is expected to have the same properties of the claimed invention. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims.
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 3-9 are rejected under 35 U.S.C. 103 as being unpatentable over Beers et al. (US2013/0048963A1, hereinafter "Beers").
Regarding instant claims 3-6, Beers discloses that the light emitting device containing an organometallic complex of General Formula 1 of Beers may be used in conjunction with other materials as a host including a pi electron-deficient nitrogen containing group, hereinafter referred as “Triazine Compound of Beers,” shown below (pg 35, Table 1).
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The pi electron-deficient triazine compound above is a compound of instant claim 4 wherein: L61 to L63 is each a single bond, b61 to b63 is 1, X64-X66 is each N, R61 and R62 is phenyl, and R63 is a C18 heterocyclic group substituted with one R10a that is phenyl. Therefore, the Triazine Compound of Beers reads on instant claim 4. Note that as only one of the second, third, and fourth compound are required, the triazine compound reads on claim 3.
Beers further discloses that the host compound may contain at least one of the following groups containing a carbazole, hereinafter referred as “Carbazole Group of Beers, shown below (pg 33, ¶ [0110]).
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The Carbazole Group of Beers is a group of instant claim 5 represented by Formula 3 wherein ring CY71 and CY72 are each independently a pi-electron rich phenyl and X71 is a single bond. R1 of the Carbazole Group of Beers is a binding site to a neighboring atom. Therefore, the Carbazole Group of Beers above meets instant claim 5.
Beers further discloses that many hole injection materials, hole transporting materials, host materials, dopant materials, exciton/hole blocking layer materials, electron transporting and electron injecting materials may be used in an OLED device (pg 35, ¶ [0127]). Another example of this material includes a boron- and nitrogen-containing tetradentate platinum complex, hereinafter referred as “B-N Pt Complex of Beers, shown below (pg 61, Table 1).
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The B-N Pt Complex of Beers reads on the fourth compound of instant claim 6, where the Pt ligand contains at least one cyclic group including nitrogen and boron as a ring-system forming atom. Therefore, a light-emitting device of Beers containing Compound 47 as the first compound, Triazine Compound of Beers as the second compound, Carbazole Compound of Beers as the third compound, and B-N Pt Complex of Beers as the fourth compound also reads on claim 3.
Regarding instant claim 7-9, Beers teaches an organic light emitting device with a “wide variety of hosts, transport layers, blocking layers, injection layers,electrodes and other layers that may be present” (¶ [0089]). These layers read on the source and drain electrodes of instant claim 8 that functions as the site for the flow of charge carriers. Beers further teaches that the organic light emitting device is a consumer product, and, in another aspect, the device may comprise a lighting panel (¶ [088]). A lighting panel in a consumer product may include a touch screen and a polarizing layer; therefore, the device of Beers reads on claim 9.
Claims 1, 7, 10-14, 16, 18, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Fleetham et al. (KR20220142398, hereinafter "Fleetham"). Note that a machine-generated translation is provided with this office action.
Regarding claim 1, Fleetham teaches an organic light-emitting device comprising an organic layer disposed between the anode and cathode layers (claim 20). The organic layer comprises an organometallic compound that follows the General Formula II of Fleetham (original pg 4). Fleetham teaches that a compound of General Formula II may follow a more specific general formula Pt(LA’)(LY) shown below (original pg 6).
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Fleetham further teaches ligand fragments, hereinafter referred to as “Ligand A” (List 2) and “Ligand B” (List 3), that may be used in General Formula Pt(LA’)(LY), both shown below (original pg 7-11).
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Ligand A of Fleetham List 2 demonstrates that the benzimidazobenzimidazole moiety, hereinafter referred to as “bim,” is an appropriate group for ring A of General Formula II of Fleetham, wherein bim is connected to the metal center at the N-imidazole position. Ligand B of Fleetham List 3 demonstrates that the bim moiety is an appropriate group for ring F of General Formula Pt(LA’)(LY), wherein bim is connected to the Pt-center at the N-imidazole position. Therefore, bim is a known and acceptable group for use in either: (1) ring A of General Formula II of Fleetham and (2) Ring F of General Formula Pt(LA’)(LY), wherein the N-imidazole position is connected to platinum.
Fleetham further teaches preferred embodiments of General Formula II and General Formula Pt(LA’)(LY) including Compound A of Fleetham and Compound B of Fleetham, both shown below (original pg 36, 39).
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Compound A of Fleetham is a compound of General Formula II where M is Pt, Ring B is phenyl, L2 is O, Ring C is carbazole, Ring D is a 4-tertbutylpyridine. Compound B of Fleetham is a compound of General Formula Pt(LA’)(LY) where Ring F is bim. Therefore, a platinum organometallic complex where Ring B is phenyl, L2 is O, Ring C is carbazole, Ring D is a 4-tertbutylpyridine for General Formula II of Fleetham is a known and acceptable ligand. In addition, a platinum organometallic complex where Ring A or Ring D of General Formula II is bim is a known and acceptable moiety.
Fleetham also teaches that compounds similar to Compound A and Compound B of General Formula Pt(LA’)(LY) a significant performance improvement in the blue-shifted triplet energy, making them suitable as deep blue OLED emitters.
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 substituted the bim moiety as ring A of General Formula II of Fleetham in Compound A of Fleetham, based on the teaching of Fleetham. The motivation for doing so would have been to achieve a platinum organometallic complex with a blue-shifted triplet energy suitable for use in an organic light emitting device.
Furthermore, given the teachings of Fleetham, 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 bim moiety of Ring A of General Formula II for Compound A of Fleetham. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the resulting organoplatinum complex of Fleetham would possess the benefits of a blue shifted triplet energy suitable for use in an organic light emitting device as taught by Fleetham. See MPEP § 2143.1.(B).
The resulting modified compound of Fleetham is shown below and is referred to hereinafter as “Modified Compound of Fleetham.”
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The Modified Compound of Fleetham is a compound of instant Formula 1-1 wherein:
M is platinum (Pt);
CY1 is phenyl and represented by Formula CY1(1) wherein;
X1 is C;
CY2 is carbazole and represented by Formula CY2(5) wherein;
X2 is C;
CY3 is pyridine and represented by Formula CY3(4) wherein;
R33 is tert-butyl and a3 is 1;
X1 is C, X2 is C, and X3 is N;
X21 is C;
Y1 to Y4 is C;
L1 is single bond;
L2 is O;
L3 is single bond;
Z1 and Z2 is bonded together to form a phenyl;
Z3 and Z4 is bonded together to form a phenyl;
Formula 101 is represented by CYN(21).
Therefore, the Modified Compound of Fleetham reads on instant claims 1, 7, 10-14, 16, 18, and compound 1 of claim 20.
Claims 1, and 10-20 are rejected under 35 U.S.C. 103 as being unpatentable over Li et al. (US2012/0215001A1, hereinafter "Li"), in view of Beers et al. (US2013/0048963A1, hereinafter "Beers"), and also in view of Chen et al. (US2020/0220090A1, hereinafter "Chen '090").
Li teaches, in the art of organic light-emitting diodes, an organometallic complex with a tetradentate ligand containing a connected ring system of Ar1, Ar2, Ar3, and Ar4 illustrated by the General Formula of Li shown below (pg 1, ¶ [0008]). Ar1 to Ar4 is defined as an aromatic ring or heterocyclic group.
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Li further teaches preferred embodiments of the General Formula of Li, including Compound Pt-009 shown above. Compound Pt-009 is a compound of the General Formula of Li where M is Pt, Ar1 is pyridine, Ar2 is carbazole, Ar3 is phenyl, Ar4 is a substituted pyrazole, and Ar2-Ar3 is connected via O.
Li fails to teach Ar4 as a benzimidazobenzimidazole or “bim” moiety, as well as specific and preferred substitutions of the complex on Ar1 to Ar4.
In the relevant art of organic light-emitting devices, Beers teaches Compound 47, shown below, which is a compound of the General Formula of Li where Ar4 is dihydroimidazoimidazole or “dim” (Beers, pg 80)
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Beers further teaches that compounds containing a substituted imidazole similar to Compound 47 are compounds suitable for use in an organic light-emitting device displaying a narrow emission and a higher triplet energy (¶ [135]-[143], Table 3-4).
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 “dim” as the group corresponding to Ar4 in the General Formula of Li,
based on the teaching of Beers. The motivation for doing so would have been to
obtain a narrow emission and higher triplet energy.
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 Li and possessing the benefits taught by Beers. One of ordinary skill in the art would have been motivated to produce additional compounds represented by the
General Formula of Li comprising compounds having the benefits taught by Beers 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 resulting Modified Intermediate 1 of Li and Beers is shown below.
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The combination of Beers and Li fails to teach specific and preferred substitutions on the “dim” moiety as Ar4 of General Formula of Li as well as on Ar1 to Ar3. The combination of Beers and Li also fails to teach a motivation for combining prior art elements, specifically to add additional steric bulk at the Ar4 position.
In the relevant art of organic light-emitting devices, Chen ‘090 teaches Compound A of Chen ‘090 shown below, which is a compound of General Formula of Li where Ar1 is 4-tertbutylpyridine, Ar2 is methyl-benzoimidazoimidazole or “mbim,” Ar3 is phenyl, and Ar4 is a substituted benzimidazole (pg 64, ¶ [0090]).
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Chen ‘090 further teaches that compounds similar to Compound A, such as Compound 271817738 where Ar1 is 4-tertbutylpyridine, Ar2 is “mbim,” Ar3 is phenyl, and Ar4 is a substituted benzimidazole, are suitable for use in an OLED device (pg 133, Table 1-2). Chen ‘090 teaches that Compound 271817738 displays a small dihedral angle between the pyridine ring and benzimidazole, leading to a bluer triplet state energy; in addition, small dihedral angles represent less distortion of the square planar geometry for better chemical stability and device lifetime (pg 133, ¶ [0142] – [0145]).
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 “mbim” as the group corresponding to Ar4 in the General Formula of Li for the Intermediate Compound 1 of Li and Beers, based on the teaching of Chen ‘090. Li and Beers teaches that N-attachment to the Pt metal center and an N-attachment to Ar3 is appropriate for the “dim” moiety. Chen ‘090 also teaches that a benzimidiazole is a known and appropriate moiety for Ar4 of the general compound of Li. Thus, the selection of “mbim” for Ar4 could also be viewed as the additional substitution of phenyl groups on “dim.” The motivation for doing so would have been to decrease the dihedral angle between the Ar1 (pyridine) and Ar4 (mbim) moieties of the tetradentate ligand to achieve a bluer triplet state and longer chemical stability.
The resulting Modified Compound II of Li, Beers, and Chen ‘090 is shown below.
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The Modified Compound II of Li, Beers, and Chen is a compound of instant Formula 1-1 wherein:
M is platinum (Pt);
CY1 is phenyl and represented by Formula CY1(1) wherein;
X1 is C;
CY2 is carbazole and represented by Formula CY2(5) wherein;
X2 is C;
CY3 is pyridine and represented by Formula CY3(4) wherein;
R33 is tert-butyl and a3 is 1;
X1 is C, X2 is C, and X3 is N;
X21 is C;
Y1 to Y4 is C;
L1 is single bond;
L2 is O;
L3 is single bond;
Z1 and Z2 is bonded together to form a phenyl;
Z3 and Z4 is bonded together to form a phenyl;
Formula 101 is represented by CYN(21) and;
Z15 is methyl.
Therefore, the Modified Compound II of Li, Beers, and Chen ‘090 reads on instant claims 1, 10-16, and 18.
Regarding instant claim 17, the Modified Compound II of Li, Beers, and Chen ‘090 is a compound of instant Formula 1-1 where R3 is tert-butyl. Beers teaches Compound 47 which is a compound of General Formula 1 of Beers. Beers defines each aryl group of Compound 47, including the imidazole, Ring A, Ring B and Ring C to be substituted with R2, R1, R3, and R4 respectively (Beers pg 17, ¶ [0061]). Beers then defines R1 to R4 as each independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, as well as other substitutions (Beers pg 17, ¶ [0062]). Thus, the substitution of the General Formula of Beers would read on the limitations of instant R1 and R2.
Regarding claim 19, the Modified Compound II of Li, Beers, and Chen ‘090 is a compound of claimed invention instant Formula 1-1 above but does not expressly teach the compound having a triplet metal to ligand charge transfer (3MLCT) value of 10% or more. It is reasonable to presume that the 3MLCT value of 10% or more is inherent to Modified Compound II. Support for said presumption is found in that the instant specification discloses that embodiments represented by Formula 1-1 may have a 3MLCT value of about 10% or more. The Modified Compound II is a compound of Formula 1-1 wherein CY1 is pheny1, CY2 is carbazole, CY3 is 4-tertbutylpyridine, and Y1 to Y4 is substituted such that the unit is “mbim,” resembling compound 1 in instant claim 20. Furthermore, the instant specification discloses that calculated values of 3MLCT for instant compound 1 is above 10% which shares a CY1 phenyl ring, CY2 carbazole, and CY3 4-tertybutylpyridine in common with Modified Compound II. Therefore, Modified Compound II is expected to have the same properties of the claimed invention. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims.
Regarding instant claim 20, Chen ‘090 teaches the Ligand LZ41 displaying an unsubstituted bim, “benzimidazobenzimidazole”, ligand. This ligand would represent the Modified Compound II of Li, Beers, and Chen ‘090 where the “mbim” ligand does not contain a methyl. The resulting compound would read on instant Compound 1 of instant claim 20.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure includes Chen et al. (US2020/0216481A1).
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/L.Q.N./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786