DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Please Note: This Application has been transferred to Examiner Yong Chu.
Claim 20 has been amended. Claims 1-20 are pending. Claims 6 and 14 were withdrawn.
Terminal Disclaimer
The terminal disclaimer filed on 05/15/2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of U.S. Patent No. 12,103,942 has been reviewed and accepted. The terminal disclaimer has been recorded.
Response to Amendments
The Amendments by Applicants’ representative Dr. Brandon A. Chan filed on 05/14/2026 has been entered.
Response to Arguments/Amendments
Claim rejection-Improper Markush Grouping
Applicant’s argument is on the ground that the compounds of the instant claims all find a common use as phosphorescent emitters such that the recitation of alternatives as provided in the instant claims is proper. Applicant’s argument has been fully considered, but is not persuasive.
According to MPEP 2117, A Markush claim contains an “improper Markush grouping” if either: (1) the members of the Markush group do not share a “single structural similarity” or (2) the members do not share a common use. Supplementary Guidelines at 7166 (citing In re Harnisch, 631 F.2d 716, 721-22, 206 USPQ 300, 305 (CCPA 1980)). For the instant application, claim 1 is drawn to a compound comprising a metal M and a first ligand LA of the structure of Formula (I), and dependent claim 4 further limits the first ligand LA selected from the group consisting of 5 distinct formula (II)
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, formula (III)
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, formula (IV)
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, formula (V)
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, and formula (VI)
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, wherein ring C is a 5-membered or 6-membered aromatic ring; X1 to X4 are each independently C or N; no more than three of X1 to -X4 is N; the X1 to X4 that is attached to ring C is C; Rc represents mono to the maximum allowable substitutions, or no substitution; each Rc is a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof, and any two substituents can be joined or fused to form a ring; Z is C or N; LA is coordinated to M to form a 5-membered chelate ring; the M coordinated to LA can be coordinated to other ligands; LA can be linked to the ligands to form a tridentate, tetradentate, pentadentate, or hexandentate ligand; and any two substituents can be joined or fused together to form a ring.
It can be easily recognized by one ordinary skilled in the art that the ligand compounds LA of Formulae (II-VI) do not share a common core. For example, the ligand of Formula (IV) has two moieties each with one bonding site linked by a single bond, and complexes with the metal M, while the ligand of Formula (V) has only one moiety with two bonding sites complexing with the metal M; and the ligand of Formulae (III) has four rings fused together forming the upper moiety, while the ligand of Formula (IV) has three rings fused together forming the upper moiety. Therefore, the ligand compounds LA of Formulae (II-VI) do not share a “single structural similarity” toward the common utility. Therefore, claims 1-5, 7-13 and 15-20 are indeed "improper Markush grouping", and the rejection is maintained.
Claim rejection under 35 U.S.C.§103(a)
Applicant’s argument is on the ground that Koo (US 2011/0057559 A1) relates to host compounds (see, e.g., [0138], [0170]) in which the host compound can be used with an Ir dopant that is a separate component and not something added further to Koo's general formula or the above formula 4 to form a coordinate complex. Thus, the Office's assertion that Koo's compound can be coordinated to a metal is merely conclusory and relies merely on common knowledge without evidentiary support.
Based on Applicant’s argument above, it can be understood that the claimed compounds of claim 1 is a compound comprising a metal M complexing with a first ligand to form a coordinate complex. Koo [0072-0073] discloses the compound of Chemical Formula 4
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[0073] is encompassed by the compound of Chemical Formula 1. Koo [0072-0073 and 0170] discloses the compound of Chemical Formula 1 (including the compound of Formula 4) is used as a host, and the compound may be used together with an iridium (Ir)-based dopant. Koo [0170-0171] further discloses the specific iridium (Ir)-based complexes (function as a dopant). Because the compound of Chemical Formula 1 (including the compound of Formula 4) is used as a host, not as a ligand in the iridium (Ir)-based complexes, the Chemical Formula 1 (including the compound of Formula 4) disclosed by Koo is not ligand for complexing with metal Ir. Therefore, Koo would have not rendered claims 1-5, 7-13 and 15-19 obvious. For the same reason, Koo would have not rendered claim 20 obvious. The rejection is hereby withdrawn.
Claim rejection under Obviousness-type Double Patenting
The Terminal Disclaimer filed by Applicants on 05/15/2026 over U.S. Patent No. 12,103,942 overcomes the ODP rejection. The rejection is hereby withdrawn.
Response to Restriction Requirement
Applicants elected species of the compound IrLC17(LA47)2
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disclosed in paragraph [0150] of Specification is acknowledged.
Status of the Claims
Elected and Examined Subject Matter
The Examiner examined the Markush-type claim with respect to Applicant’s elected species. Since the elected species was found clear of prior art, the examination of the Markush-type claim was extended, further to the extent to determine patentability, pursuant to MPEP§ 803.02 “Election of Species Requirements – Markush Claims”. The scope of examined subject matter is set as following:
A compound comprising a metal M complexing with a first ligand LA comprising the structure of formula (IV)
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according to claim 4, wherein M is Ir; an organic light emitting device (OLED) comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising the compound thereof; a consumer product comprising an organic light-emitting device (OLED) comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising the compound thereof; a formulation comprising the compound thereof; an organic light emitting device (OLED) comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a host compound, and further comprising an emitter compound thereof, wherein the compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature.
As a result of the election of the subject matter above, part of claims 1-5, 7-13, and 15-20, which is outside the elected scope above is withdrawn from further consideration pursuant to 37 CFR 1.142 (b) as being drawn to non-elected inventions. The withdrawn compounds contain varying functional groups which are chemically recognized to differ in structure, function, and reactivity. The withdrawn groups are drawn to different inventions. The scope of the invention is set in considering the elected species and the preferred embodiments. Therefore, claims 1-5, 7-13, and 15-20 (in part) are under examination on the merits.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 of this title, 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.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1-5, 7-13, and 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over US2018/0130962 (“the `962 publication”) to Ji et al., published on May 10, 2018.
Applicant’s claim 1 is drawn to a compound comprising a metal M complexing with a first ligand LA comprising the structure of Formula I
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, wherein the Formula 1 is the Formula IV
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according to claim 4.
Determination of the scope and content of the prior art (MPEP §2141.01)
The `962 publication ([0085-0086], claims 14 and 25) discloses a composition comprising a first compound wherein the first compound is capable of functioning as an emitter in an organic light emitting device at room temperature; wherein the first compound has the formula of M(L1)x(L2)y(L3)z wherein L1, L2 and L3 can be the same or different; wherein at least one of L1, L2 and L3 is not acetylacetonate ligand; x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; wherein x+y+z is the oxidation state of the metal M; wherein L1, L2 and L3 are each independently selected from the group consisting of
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,
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(Ligand 11),
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(Ligand 12),
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(Ligand 13),
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(Ligand 17),
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(Ligand 15),
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(Ligand 16), etc., wherein Z1 and Z2 are CR1R2, wherein R1 and R2 are independently a hydrogen, a deuterium, or a substituent alkyl.
In addition, the `962 publication (claim 31) discloses an organic light-emitting device (OLED) comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a first compound wherein the first compound is capable of functioning as an emitter in an organic light emitting device at room temperature disclosed above, and a host, wherein the host compound is selected from the group consisting of
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(the 1st compound of Applicant’s claim 20),
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(the 2nd compound of Applicant’s claim 20),
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(the 4th compound of Applicant’s claim 20),
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(the 5th compound of Applicant’s claim 20),
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(the 6th compound of Applicant’s claim 20), etc.
Ascertainment of the difference between the prior art and the claims (MPEP §2141.02)
The difference between the instantly claimed ligand compounds of Formula (IV) and the Ligands (11-13 and 15-17) of the `962 publication (claim 25) is that the `962 publication (claim 25) does not teach at least one of R¹, R², R³, and R⁴ (in Z¹ and Z² of the Formula I of claim 1) is a fluorine atom. Instead, the Ligands (11-13 and 15-17) of the `962 publication (claim 25) have R¹, R², R³, and R⁴ are each independently alkyl, and/or partially or fully deuterated variants thereof.
Finding of prima facie obviousness--rational and motivation (MPEP §2142-2413)
However, the instant claims would have been obvious over the `962 publication beause the `962 publication (claim 6) teaches R3 to R6 are each independently selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, which reads on Applicant’s claims wherein at least one of R¹, R², R³, and R⁴ (in Z¹ and Z² of the Formula I of claim 1) is a fluorine atom. One ordinary skilled in the art would have been motivated to replace alkyl (Ligands 15-16) with partially or fully fluorinated variants thereof based on the disclosure of partially or fully deuterated variants thereof (Ligands 11-13 and 17). Therefore, the difference is further taught and/or suggested by the same prior art. The `962 publication would have rendered claims 1-5, 8-11, 13, and 15-20 obvious.
In terms of claim 7 wherein M is Ir, the `962 publication (claim 15) teaches the first compound has the formula of Ir(L1)2(L2), wherein M is Ir.
In terms of claim 12 wherein M is Ir, the `962 publication (claim 15) teaches the first compound has the formula of Ir(L1)2(L2), wherein M is Ir.
Obviousness-Type 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 obviousness-type 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); and 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 a nonstatutory double patenting ground provided the conflicting application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement.
Effective January 1, 1994, a registered attorney or agent of record may sign a terminal disclaimer. A terminal disclaimer signed by the assignee must fully comply with 37 CFR 3.73(b).
Claims 1-5, 7-13, and 15-20 are rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over claims 1-3, and 5-20 of U.S. Patent No. 10,680,187 (“the `187 patent”, equivalent to the `962 publication). Although the conflicting claims are not identical, they are not patentably distinct from each other because instant claims 1-5, 7-13, and 15-20 and claims 1-3, 5-20 of the `598 patent are drawn to overlapped scope of a compound comprising a metal M complexing with a first ligand LA comprising the structure of Formula I
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, wherein the Formula 1 is the Formula IV
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according to claim 4.
The `187 patent ([0085-0086], claims 14 and 25) discloses a composition comprising a first compound wherein the first compound is capable of functioning as an emitter in an organic light emitting device at room temperature; wherein the first compound has the formula of M(L1)x(L2)y(L3)z wherein L1, L2 and L3 can be the same or different; wherein at least one of L1, L2 and L3 is not acetylacetonate ligand; x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; wherein x+y+z is the oxidation state of the metal M; wherein L1, L2 and L3 are each independently selected from the group consisting of
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,
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(Ligand 11),
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(Ligand 12),
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(Ligand 13),
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(Ligand 17),
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(Ligand 15),
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(Ligand 16), etc.
In addition, the `187 patent (claim 31) discloses an organic light-emitting device (OLED) comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a first compound wherein the first compound is capable of functioning as an emitter in an organic light emitting device at room temperature disclosed above, and a host, wherein the host compound is selected from the group consisting of
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(the 1st compound of Applicant’s claim 20),
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(the 2nd compound of Applicant’s claim 20),
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(the 4th compound of Applicant’s claim 20),
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(the 5th compound of Applicant’s claim 20),
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(the 6th compound of Applicant’s claim 20), etc.
The difference between the instantly claimed ligand compounds of Formula (IV) and the Ligands (11-13 and 15-17) of the `187 patent (claim 25) is that the `187 patent (claim 25) does not teach at least one of R¹, R², R³, and R⁴ (in Z¹ and Z² of the Formula I of claim 1) is a fluorine atom. Instead, the Ligands (11-13 and 15-17) of the `187 patent (claim 25) have R¹, R², R³, and R⁴ are each independently alkyl, and partially or fully deuterated variants thereof.
However, the instant claims would have been obvious over the `187 patent beause the `187 patent (claim 6) teaches R3 to R6 are each independently selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, which reads on Applicant’s claims wherein at least one of R¹, R², R³, and R⁴ (in Z¹ and Z² of the Formula I of claim 1) is a fluorine atom. One ordinary skilled in the art would have been motivated to replace alkyl (Ligands 15-16) with partially or fully fluorinated variants thereof based on the disclosure of partially or fully deuterated variants thereof (Ligands 11-13 and 17). Therefore, the difference is further taught and/or suggseted by the same prior art. The claims of the `187 patent would have rendered Applicant’s claims 1-5, 8-11, 13, and 15-20 obvious.
In terms of claim 7 wherein M is Ir, the `962 publication (claim 15) teaches the first compound has the formula of Ir(L1)2(L2), wherein M is Ir.
In terms of claim 12 wherein M is Ir, the `962 publication (claim 15) teaches the first compound has the formula of Ir(L1)2(L2), wherein M is Ir.
Allowable subject Matters
The elected species of the compound IrLC17(LA47)2
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disclosed in paragraph [0150] of Specification is allowable if amended into an independent claim.
Conclusions
Claims 1-5, 7-13, and 15-20 are rejected.
Claims 6, and 14 remain withdrawn.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Yong L. Chu, whose telephone number is (571)272-5759. The examiner can normally be reached on M-F 8:30am-5:00pm.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amber R. Orlando can be reached on 571-270-3149. The fax phone number for the organization where this application or proceeding is assigned is (571) 273-8300.
/YONG L CHU/Primary Examiner, Art Unit 1731
Prosecution Insights