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 .
Specification
The disclosure is objected to because of the following informalities: the specification contains chemical formulas that are low quality and pixelated such that atom labels are difficult to decipher including, but not limited to, the formulas reproduced below (¶ [0130], [0132]).
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Appropriate correction is required.
Claim Objections
Claim 19 is objected to because of the following informalities: the claims contains chemical formulas that are low quality and pixelated such that atom labels are difficult to decipher including, but not limited to, the formulas reproduced below.
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Appropriate correction is required.
Claim Rejections - 35 USC § 102
(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.
Claims 1-2, 8-9 and 12 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Park et al. (KR 20130130110934 A, hereinafter "Park"). 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, Park discloses an organometallic compound to obtain an organic electroluminescent device with excellent thermal properties, light emitting efficiency, and color purity, thereby being used in a display (abstract). Park discloses the Compound 173, shown below (pg 15).
Compound 173
Compound 173 CAPLUS Record
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The Compound 173 of Park is a compound of instant Formula 1 of instant claim 1 wherein:
M is 2 and N is 1;
D is a monocyclic ring and is a 6-membered carbocyclic;
R is hydrogen;
RA is hydrogen;
RB is arylalkyl or “pentafluoro-phenyl”;
R1 – R3 are alkyl “methyl”;
R4 – R5 is hydrogen;
R6 is silyl “trimethyl silyl”;
RC is hydrogen;
RD and silyl “trimethyl silyl”
RE is hydrogen;
Statement (2) is true because R6 comprises three carbon atoms wherein R6 is a silyl group “trimethyl silyl” which has three carbons.
Therefore, the compound 173 of Park anticipates claims 1-2.
Regarding claim 8, the compound 173 of Park anticipates the compound of claim 1 wherein moiety D is selected from the group consisting of benzene.
Regarding claim 9, the compound 173 of Park anticipates the compound of claim 1 wherein the ligand LA is selected from the group consisting of:
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Regarding claim 12, the compound 173 of Park anticipates the compound of claim 1 wherein the ligand LB is selected from the group consisting of:
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Wherein X1 is C and RDD represents silyl or “trimethyl silyl”.
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 1-6 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Hwang et al. (US 2016/0155963 A1, hereinafter "Hwang").
In the pertinent art of organic light-emitting devices, Hwang teaches an organometallic compound represented by Formula 1: M(L1)n1(L2)n2 wherein L1 is selected from ligands represented by Formula 2 and L2 is selected from monovalent , divalent, trivalent, and tetravalent organic ligands (¶ [0008] – [0014]).
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Formula 2 of Hwang
Hwang teaches specific compounds of the Formula 2 of Hwang including compounds 62 and 142 (pg 55, 65). Compound 62 features polycyclic silicon-containing ring system wherein the silicon has a dimethyl substitution whereas Compound 142 features a similar polycyclic silicon-containing ring system wherein the silicon has a diethyl substitution, shown below.
Compound 62
Compound 142
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Hwang teaches that the organic light-emitting device with the organometallic compound represented by Formula 1 features a low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (¶ [0230]).
Hwang teaches the above, however, Hwang does not teach a compound of Formula 1 wherein the Compound 62 features a diethyl substitution for the silicon polycyclic 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 include the diethyl silicon substitution of Compound 62 in the light-emitting device of Hwang, based on the teachings of Hwang. The motivation for doing so would have been to obtain a device with a low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color, as taught by Hwang (¶ [0230]). The resulting Modified Compound 62 of Hwang is shown below.
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Modified Compound 62 of Hwang
The Modified Compound 62 of Hwang is a compound of instant Formula 1 of instant claim 1 wherein:
M is 2 and N is 1;
D is a monocyclic ring and each ring is 6-membered carbocyclic;
R is methyl;
RA is hydrogen;
R1 – R3 are alkyl “methyl”;
R4 is substituted silyl and RC is joined to form a fused ring;
R5 – R6 is hydrogen;
RC is substituted silyl and R4 is joined to form a fused ring;
RD and RE are hydrogen;
Statement (1) is true because R4 comprises four carbon atoms (diethyl silyl).
Therefore, the Modified Compound 62 of Hwang reads on instant claims 1-2.
Regarding claim 11, the Modified Compound 62 of Hwang reads on claim 11 as a compound of claim 1 wherein ligand LA is selected from LA3.
Regarding claim 3, Hwang teaches Compound 26 (pg 51) wherein the pyridine group features a -CD3 substitution, shown below.
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Compound 26 of Hwang
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 include the -CD3 group in the Modified Compound 62 of Hwang in the light-emitting device of Hwang, based on the teachings of Hwang. The motivation for doing so would have been to obtain a device with a low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color, as taught by Hwang (¶ [0230]). The resulting Modified Compound II-62 of Hwang is shown below, and reads on claim 3 wherein instant RA is selected from alkyl that is fully deuterated.
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Modified Compound II-62 of Hwang
Regarding claim 4, Hwang teaches the ring corresponding to instant ring B may be joined together to form a fused ring selected from the group of naphthalene as shown in Compound 40, shown below (pg 52).
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Compound 40 of Hwang
Regarding claim 5, the Modified Compound II-62 of Hwang is a compound of claim 1 wherein at least one RC adjacent to the bond with Ring E is selected from the group consisting of heteroaryl wherein ring E is joined to form a fused heteroaryl ring.
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Modified Compound II-62 of Hwang
Regarding claim 6, the Modified Compound II-62 of Hwang contains R1 to R3 as alkyl.
Claims 7, 10, 13-18, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Park et al. (KR 20130130110934 A, hereinafter "Park") as applied to claims 1-2, 8-9, and 12 described above.
Park teaches the compound 173 that reads on claims 1-2 as described above wherein the compound 173 contains a group corresponding to instant Ring E as phenylene and R6 is trimethyl silyl or “TMS”. Park does not necessarily limit the group on the pyridine ligand to just a TMS-phenylene group. Park teaches compound 54 wherein the pyridine group attached to the Ir center may be substituted with other substituted phenylene groups such as a phenylene substituted with an additional phenyl group that is joined with a nitrogen atom to make the fused ring “carbazole” shown below (pg 10).
Compound 173
Compound 54
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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 include the substituted carbazole group in the compound 173 of Park in the light-emitting device of Park, based on the teachings of Park. The motivation for doing so would have been to obtain a device with excellent thermal properties, light emitting efficiency, and color purity, as taught by Park (abstract).
The resulting Modified Compound 54 of Park is shown below and reads on claim 7 wherein R6 is a substituted arylalkyl group and R6 comprises 6 carbon atoms or “phenylene substituted with nitrogen and a trimethyl silyl group” and RE is a nitrogen atom wherein R6 and RE are joined to form a ring fused to Ring E and wherein ring E plus the ring fused to ring E form a moiety consisting of carbazole.
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Modified Compound 173 of Park
Park teaches the Compound 173 of Park, described above, as a compound of Park’s Chemical Formula 1 (pg 3), shown below, wherein the ring A2 is substituted by R5 which is a pentafluoro-phenyl; however, Park does not necessarily limit R5 to pentafluoro-phenyl. Park also does not necessarily limit R4 to hydrogen.
Chemical Formula 1
Compound 173
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Park teaches that R4 and R5 is each independently comprising a hydrogen, deuterium, alky, aryl, hetero aryl, and other groups (Description pg 3-4). In addition, Park teaches compound 7 wherein R4 is methyl and R5 is fluorine, shown below (Description pg 7).
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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 further include the R4 as methyl and R5 as fluorine in the compound 173 of Park in the light-emitting device of Park, based on the teachings of Park. The motivation for doing so would have been to obtain a device with excellent thermal properties, light emitting efficiency, and color purity, as taught by Park (abstract).
The resulting Modified Compound II-173 of Park is shown below, and reads on claim 10 wherein the ligand LA is selected from the group consisting of:
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Wherein RA1 and RA2 are selected from alkyl or “methyl” and RB2 is selected from arylalkyl or “pentafluorophenylene” and RB1 is selected from halogen or “fluorine.”
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Modified Compound II-173 of Park
Regarding claim 13, Park teaches the compound 8, shown below, wherein the R5 is hydrogen and the phenylene group is unsubstituted. 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 include the R5 as hydrogen in the compound 173 of Park in the light-emitting device of Park, based on the teachings of Park. The motivation for doing so would have been to obtain a device with excellent thermal properties, light emitting efficiency, and color purity, as taught by Park (abstract).
The resulting Modified Compound III-173 of Park is shown below and reads on claim 13 wherein LB is selected from:
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.
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Modified Compound III-173 of Park
Regarding claim 14, Park teaches the compound 173 that features a phenylpyridine ligand wherein the pyridine skeleton is substituted with a phenyl-TMS group and the phenyl pyridine is substituted with a TMS group as described above. Park teaches additional compounds wherein other known and acceptable groups appropriate for the substitution of the phenylpyridine ligand are described below:
The compound 126 teaches that the phenyl-pyridine ligand may contain a substitution on phenyl that is unsubstituted phenyl (Description pg 13)
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The compound 148 teaches that the pyridine may be substituted with substituted-phenyl at any position of the pyridine; and the substituted-phenyl contains two identical alkyl groups methyl (Description pg 14)
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Park teaches that methyl is a known and acceptable alkyl group for substitution in the Formula 1 of Park as described above. Park also teaches the compound 12 wherein the isopropyl group is a known and acceptable alkyl group for substitution in the Formula 1 of Park (Description pg 8).
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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 further modify the compound 173 of Park with (1) an unsubstituted phenyl group at the phenyl skeleton; (2) a dialkyl group on the phenyl group attached to the pyridine skeleton; and (3) wherein the dialkyl group is isopyropyl group in the light-emitting device of Park, based on the teachings of Park. The motivation for doing so would have been to obtain a device with excellent thermal properties, light emitting efficiency, and color purity, as taught by Park (abstract).
The resulting Modified Compound IV-173 of Park is shown below.
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Modified Compound IV-173 of Park
Therefore, the Modified Compound IV-173 of Park reads on claim 14 wherein LB is selected from LB30.
Regarding claim 15, Park teaches the Modified Compound IV-173 that contains a phenylpyridine ligand substituted with a pentafluorophenyl 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 include a phenylpyridine group wherein the phenyl skeleton is unsubstituted in the Modified Compound IV-173 of Park in the light-emitting device of Park, based on the teachings of Park. The motivation for doing so would have been to obtain a device with excellent thermal properties, light emitting efficiency, and color purity, as taught by Park (abstract).
The resulting Modified Compound V-173 of Park is shown below.
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Modified Compound V-173 of Park
The Modified Compound V-173 of Park reads on claim 15 wherein the compound has formula Ir(LA)2(LB) and the compound is selected from the group consisting of Ir(LA1)2(LB30).
Regarding claim 16, Park teaches the Modified Compound V-173 of Park as described above. Park also teaches the compound 4 wherein a biphenyl group is a known and acceptable group for the pyridine skeleton, shown below (Description pg 7).
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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 further include a biphenyl group on the pyridine skeleton of the Modified Compound V-173 of Park in the light-emitting device of Park, based on the teachings of Park. The motivation for doing so would have been to obtain a device with excellent thermal properties, light emitting efficiency, and color purity, as taught by Park (abstract).
The resulting Modified Compound VI-173 of Park is shown below.
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Modified Compound VI-173 of Park
The Modified Compound VI-173 of Park reads on claim 16 because it is the same as the compound found on page 40 of the claims column III row III.
Regarding claim 17, Park teaches the organic light-emitting device Example 1 with the following structure: ITO; DNTPD, NPD, CBP and the compound of Park’s Chemical Formula 1; Alq3, LiF, and Al. Park teaches an anode, a cathode, and an organic layer and the compound of Park’s Chemical Formula 1 is in the organic layer as discussed above. It would have been obvious to use the compound 173 of Park in the organic layer with the device structure of anode, organic layer with compound 173, and cathode as Park demonstrates this device structure was known prior to the effective filing date of the claimed invention. The resulting Modified Device of Park reads on claim 17.
Regarding claim 18, the Modified Device contains the compound CBP as a host wherein CBP comprises at least the moiety selected from carbazole.
Regarding claim 20, Park teaches that the organic light-emitting device may be used in a display or a lamp which are consumer products (abstract).
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Park et al. (KR 20130130110934 A, hereinafter "Park") as applied to claims 1-2, 7-10, 12-18, and 20 described above in view of Wolohan et al. (US 2020/0168812 A1, hereinafter "Wolohan").
Regarding claim 19, Park teaches the Modified Device of Park containing CBP, which is a compound similar to the group depicted below in that they both feature at least two carbazole groups that are linked by a biphenyl moiety. However, CBP does not contain a carbazole substituted carbazole nor the attachment orientation as claimed.
Instant Host
CBP
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In the relevant art of organic light-emitting devices, Wolohan teaches an organic light-emitting device containing an emissive layer with the host Compound 3, shown below, with an organometallic dopant featuring pyridine and phenyl ligands (¶ [0171]).
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Wolohan teaches that the organic light-emitting devices of Woholan result in increased stability (¶ [0168]).
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 include the Compound 3 of Wolohan in the Modified Device of Park, based on the teachings of Wolohan. The motivation for doing so would have been to obtain a device with increased stability, as taught by Wolohan (¶ [0168]).
The resulting Modified Device II of Park and Wolohan reads on claim 19.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-2, 6, 8-9, and 11-14 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 and 21 of copending Application No. 17/959,326 (reference application, hereinafter ‘326). This is a provisional nonstatutory double patenting rejection.
Although the claims at issue are not identical, they are not patentably distinct from each other because the compounds of Formula Ir(LA)m(LB)n in instant claim 1 are obvious variants due to the overlap in scope with compounds of Formula Ir(La)x(LB)y(LC)z of application ‘326. The overlap in scope is demonstrated by the iridium organometallic complex in claim 21 of ‘326 shown below (‘326, claim 21).
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The iridium complex of claim 21 is a compound of instant claim 1 wherein:
D is a polycyclic fused-ring system independently a 5-membered or 6-membered heterocyclic ring with three fused rings “substituted dibenzofuran”;
R is selected from H;
RA and RB are H;
RC is alkyl “-CD3”;
RD is arylalkyl “phenylene”;
RE is H;
R1-R3 is silyl “TMS”;
R4 and R5 are alkyl “isopropyl”;
R6 is silyl “TMS”;
Statements (1) and (2) are true.
LA is selected from LA1 of instant claim 11
LB is selected from LB202 of instant claim 14.
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
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786
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