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
The present application claims priority to the application, 63/393,021, with the effective filing date of 28 July 2022.
Claim Status
This Office Action is in response to Applicant’s Response to Restriction Requirement filed, 22 January 2026.
Applicant's election with traverse of Group I and
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in the reply filed on 22 January 2026 is acknowledged. The traversal is on the ground(s) that a serious search burden would not be incurred given that the claims of Group II incorporate the subject matter of at least independent claim 1 of Group I.
However, this is not found persuasive, because Groups I and II are classified by different CPC symbols. Group I was assigned the CPC symbol, C07F 15/0086 (platinum compounds), and Group II was assigned the CPC symbol of H10K 59/90 (assemblies of multiple devices comprising at least one organic light-emitting element). Further, Group I consists of claims directed to compounds. However, Group II consists of claims directed to a device and parts thereof comprising layers (e.g. 3-dimensionality, morphology), an anode, and a cathode, which would require a serious search burden due to different key terms from Group I, as evidenced by McEwan (ACS Appl Mater Interfaces, 2018, 10, 3848-3855). Further, Applicant has not established that the claimed invention provides a contribution over the cited prior art in the Restriction Requirement mailed on 2 December 2025. Thus, the requirement is still deemed proper and is therefore made FINAL.
Claims 11, 12, are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected species, there being no allowable generic or linking claim. Claim 11 specifies one or more of X1, X2, X3, X4, X1’, X2’, X3’, and X4’ are nitrogen, which does not read on the elected species. Claim 12 specifies X2 and X2’ are nitrogen, which does not read on the elected species. Claim 15 specifies an aryl, heteroaryl, C1-C20 heterocycle, or fused combination thereof on the phenyl ring of the elected species (which does not exist in the elected species), and thus does not read on the elected species. Claim 16 further limits the aryl, heteroaryl, C1-C20 heterocycle, or fused combination thereof on the phenyl ring of the elected species (which does not exist in the elected species), and thus does not read on the elected species. Claim 17 further limits the aryl, heteroaryl, C1-C20 heterocycle on the phenyl ring of the elected species (which does not exist in the elected species), and thus does not read on the elected species. Claim 18 further limits the aryl, heteroaryl, C1-C20 heterocycle on the phenyl ring of the elected species (which does not exist in the elected species), and thus does not read on the elected species. Claim 19 specifies a compound of Formula IIb or IIIb, which does not read on the elected species. Claim 20 specifies a compound of Formula IIb or IIIb, which does not read on the elected species. Claim 21 specifies a compound of Formula IIb or IIIb, which does not read on the elected species. Claim 22 specifies a compound of Formula IIb or IIIb, which does not read on the elected species. Claim 23 specifies a compound of Formula IIb or IIIb, which does not read on the elected species. Claim 24 specifies a compound of Formula IIb or IIIb, which does not read on the elected species. Claim 25 specifies a compound of Formula IIb or IIIb, which does not read on the elected species. Claim 26 depends upon claim 27. For purposes of clarity, the Examiner interprets claim 26 to be dependent upon claim 25, which specifies a compound of Formula IIb or IIIb, which does not read on the elected species. Claim 27 depends upon claim 25, which specifies a compound of Formula IIb or IIIb, which does not read on the elected species. Claim 28 specifies that A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are independently carbon, nitrogen, oxygen, or sulfur, which does not read on the elected species (in the elected species, A1, A1’, A4, A4’ are hydrogen and A2, A2’, A3, A3’ are absent). Claim 29 depends upon claim 28, which specifies A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are independently carbon, nitrogen, oxygen, or sulfur, which does not read on the elected species. Claim 30 depends upon claim 28, which specifies A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are independently carbon, nitrogen, oxygen, or sulfur, which does not read on the elected species. Claim 31 depends upon claim 28, which specifies A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are independently carbon, nitrogen, oxygen, or sulfur, which does not read on the elected species. Claim 33 specifies A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, which does not read on the elected species. Claim 34 depends upon claim 33, which specifies that A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, which does not read on the elected species. Claims 35 depends upon claim 33, which specifies that A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, which does not read on the elected species. Claim 36 depends upon claim 33, which specifies that A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, which does not read on the elected species. Claim 37 depends upon claim 33, which specifies that A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, which does not read on the elected species. Claim 38 specifies that one or more of A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, oxygen, or sulfur, which does not read on the elected species (in the elected species, A1, A1’, A4, A4’ are hydrogen and A2, A2’, A3, A3’ are absent). Claim 39 depends upon claim 38, which specifies that one or more of A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, oxygen, or sulfur, which does not read on the elected species. Claim 40 depends upon claim 38, which specifies that one or more of A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, oxygen, or sulfur, which does not read on the elected species. Claim 41 depends upon claim 38, which specifies that one or more of A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, oxygen, or sulfur, which does not read on the elected species. Claim 42 depends upon claim 38, which specifies that one or more of A1, A2, A3, A4, A1’, A2’, A3’, and A4’ are nitrogen, oxygen, or sulfur, which does not read on the elected species.
Claims 44-52 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected group (Group II), there being no allowable generic or linking claim.
Drawings
The Examiner notes that Applicant may wish to submit a petition for color drawings for clarity regarding Figures 1A, 1B, 1C, and 1D.
Claim Objections
1. Claims 10, 13, and 14 are objected to because of the following informalities: depends only upon claim 5, but references a compound of Formula IIIa (claim 7). Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c).
2. Claim 1 recites the broad recitation of A and A’ are independently a substituted cycloalkyl, an unsubstituted cycloalkyl, a substituted cycloalkenyl, an unsubstituted cycloalkenyl, a substituted cycloalkynyl, an unsubstituted cycloalkynyl, a substituted C1-C20 heterocyclyl, an unsubstituted C1-C20 heterocyclyl, a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, an unsubstituted heteroaryl, a substituted polyaryl, an unsubstituted polyaryl, a substituted polyheteroaryl, an unsubstituted polyheteroaryl, or fused combinations thereof. Claim 1 also recites preferably A and A' are independently a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, an unsubstituted heteroaryl, a substituted polyaryl, an unsubstituted polyaryl, a substituted polyheteroaryl, an unsubstituted polyheteroaryl, a substituted C1-C20 heterocyclyl, an unsubstituted C1-C20 heterocyclyl, or fused combinations thereof, which is the narrower statement of the range/limitation.
3. Claim 1 further recites the broad recitation of X5, and X5' are independently carbon or nitrogen, and are independently bonded to one or no hydrogen atom according to valency. Claim 1 also recites preferably, X5 and X5' are carbon, which is the narrower statement of the range/limitation.
4. Claim 1 further recites the broad recitation of R5, R6, R5', and R6' are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted, aryl, halogen, hydroxyl, thiol, cyano, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C3-C20 cycloalkyl, unsubstituted C3-C20 cycloalkyl, substituted C1-C20 heterocyclyl, unsubstituted C1-C20 heterocyclyl, substituted C3-C20 cycloalkenyl, unsubstituted C3-C20 cycloalkenyl, substituted C3-C20 cycloalkynyl, unsubstituted C3-C20 cycloalkynyl, or R5 and R6 together, R5’ and R6' together, with the atom to which they are attached, form a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, an unsubstituted heteroaryl, a substituted C1-C20 heterocyclyl, an unsubstituted Ct-C20 heterocyclyl, fused combinations thereof. Claim 1 also recites preferably R5, R6, R5', and R6' are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, which is the narrower statement of the range/limitation.
5. Claim 3 recites the broad limitation of L and L1' are independently substituted C1-C10 to alkyl, unsubstituted C1-C10 alkyl, substituted C2-C10 alkyl or unsubstituted C2-C10 alkyl. Claim 3 also recites preferably wherein the substituted alkyl, substituted C1-C10 alkyl, substituted C2-C10 alkyl contains one or more alkyl substituents, one or more ether bonds, one or more amine groups, one or more substituted aryl groups, one or more substituted heteroaryl groups, one or more substituted C3-C20cycloalkyl groups, one or more substituted C1-C20 heterocyclyl groups. Claim 3 further narrows and recites (such as methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl) and (such as substituted amine or unsubstituted amine), which is a narrower statement of the range/limitation.
6. Claim 5 recites the broad limitation of R1, R2, R3, R4, R1’, R2’, R3’, and R4' are independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen, hydroxyl, thiol, cyano, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C3-C20 cycloalkyl, unsubstituted C3-C20 cycloalkyl, substituted C1-C20heterocyclyl, unsubstituted C1-C20 heterocyclyl, substituted C3-C20 cycloalkenyl, unsubstituted C3-C20 cycloalkenyl, substituted C3-C20 cycloalkynyl, or unsubstituted C3-C20 cycloalkynyl, or R1 and R2 together, R2 and R3 together, R3 and R4 together, R1' and R2’ together, R2’ and R3' together, R3’ and R4’ together, or a combination thereof, with the atom to which they are attached, form a substituted cycloalkyl, an unsubstituted cycloalkyl, a substituted cycloalkenyl, an unsubstituted cycloalkenyl, a substituted cycloalkynyl, an unsubstituted cycloalkynyl, a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, an unsubstituted heteroaryl, a substituted polyaryl, an unsubstituted polyaryl, a substituted polyheteroaryl, an unsubstituted polyheteroaryl, a substituted C1-C20 heterocyclyl, an unsubstituted C1-C20 heterocyclyl, or fused combinations thereof. Claim 5 also recites (such as trifluoronethyl), (such as mesityl trimethylphenyl), and (such as fluorine), which is the narrower statement of the range/limitation.
7. Claim 6 recites the broad limitation of R1, R2, R3, R4, R1’, R2’, R3’, and R4’ are independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, halogen, or R1 and R2 together, R2 and R3together, R3 and R4 together, R1' and R2' together, R2' and R3' together, R3' and R4' together, or a combination thereof, with the atom to which they are attached, form a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, an unsubstituted heteroaryl, a substituted C1-C20 heterocyclyl, an unsubstituted C1-C20 heterocyclyl, or fused combinations thereof. Claim 6 also recites (such as trifluoromethyl), (such as mesityl (2,4,6- trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), (such as fluorine), which is the narrower statement of the range/limitation.
8. Claim 13 recites the broad limitation of R1, R2, R3, R4, R1’, R2’, R3’, and R4’ are independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, halogen, or R1 and R2 together, R2 and R3together, R3 and R4 together, R1' and R2' together, R2' and R3' together, R3' and R4' together, or a combination thereof, with the atom to which they are attached, form a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, an unsubstituted heteroaryl, a substituted C1-C20 heterocyclyl, an unsubstituted C1-C20heterocyclyl, or fused combinations thereof. Claim 13 also recites (such as trifluoromethyl), (such as mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6- dimethylphenyl), and (such as fluorine), which is the narrower statement of the range/limitation.
9. Claim 14 recites the broad limitation of R1, R2, R3, R4, R1’, R2’, R3’, and R4’ independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, or halogen. Claim 14 also recites (such as trifluoromethyl), (such as mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6- dimethylphenyl), and (such as fluorine), which is the narrower statement of the range/limitation.
The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
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 (i.e., changing from AIA to pre-AIA ) 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, 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 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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
10. Claims 1-10, 13, 14, and 43 are rejected under 35 U.S.C. 103 as being unpatentable over Molt (U.S. Patent No. 9,108,998, issued 18 Aug 2015) in view of Xue (Adv. Opt. Materials, 2022, 10(2200741), 1-9).
Molt teaches dinuclear platinum-carbene complexes for OLEDs, such as
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(abstract; column 4, lines 50-65).
Molt specifically teaches
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(column 20, lines 55-65). Molt additionally teaches complexes that enable OLEDs to have long operative lifetime, good efficiency, high stability to thermal stresses, and a low use and operating voltage are of particular interest (column 1, lines 54-56). Molt further teaches that previous platinum-carbene complexes for OLEDs provided inadequate quantum yields with undesirable efficiency and stability (column 3, lines 1-5).
Molt fails to teach the compound,
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, having alkyl chain tying together the pyrazole and imidazole ligands (see reply to restriction requirement, filed 22 Jan 2026).
Xue teaches dibridged cyclometalated Pt(II) complexes with short intramolecular Pt-Pt contacts:
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(page 1, column 2, paragraph 3; page 2, Figure 1: compound 3(C)). Xue additionally teaches that efficient red and deep red phosphorescent OLEDs play pivotal roles in optoelectronic and biological application and specifies a method of accessing efficient red and deep red metal emitters via deploying structural rigid chromophoric unit(s) to suppress deactivation via vibrational quenching pathway (page 1, column 1, paragraph 1; page 1, column 2, paragraph 1). Xue further specifies that one method of developing red triplet metal emitters for Pt(II) complexes is to employ rigid pi-annulated cyclometalating ligands and that structural rigidity imposed by the [C^C*] and ditopic bridging ligand effectively reduces structural distortion induced in the 3MMLCT excited state (page 6, column 2, paragraph 2; page 7, column 1, paragraph 1; page 7, column 2, paragraph 1).
It would have been prima facie obvious to one of ordinary skill in the art, prior to the effective filing date of the instantly claimed invention to employ alkyl chains of Xue to rigidify the compounds of Molt to arrive at instant claim 1. One of ordinary skill in the art would have been motivated to make such a selection, with a reasonable expectation of success, because:
- Molt teaches dinuclear platinum-carbene complexes for OLEDs,
-Molt teaches
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,
-Molt teaches complexes that enable OLEDs to have long operative lifetime, good efficiency, high stability to thermal stresses, and a low use and operating voltage are of particular interest,
-Molt teaches previous platinum-carbene complexes for OLEDs provided inadequate quantum yields with undesirable efficiency and stability,
-Xue teaches dibridged cyclometalated Pt(II) complexes with short intramolecular Pt-Pt contacts:
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,
-Xue teaches that efficient red and deep red phosphorescent OLEDs play pivotal roles in optoelectronic and biological application and specifies a method of accessing efficient red and deep red metal emitters via deploying structural rigid chromophoric unit(s) to suppress deactivation via vibrational quenching pathway, and
-Xue teaches that one method of developing red triplet metal emitters for Pt(II) complexes is to employ rigid pi-annulated cyclometalating ligands and that structural rigidity imposed by the [C^C*] and ditopic bridging ligand effectively reduces structural distortion induced in the 3MMLCT excited state.
Additionally, structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093- 95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers); In re Wilder, 563 F.2d 457, 460, 195 USPQ 426, 429 (CCPA 1977) (adjacent homologs and structural isomers); In re Hoch, 428 F.2d 1341, 1344, 166 USPQ 406, 409 (CCPA 1970) (acid and ethyl ester); In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring). Generally, some teaching of a structural similarity will be necessary to suggest selection of the claimed species or subgenus. The closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). See MPEP § 2144.08(II)(A)(4)(c). As the compound taught by the combination of Molt and Xue differs from the elected compound in the change from a methyl to a hydrogen (on the phenyl ring), a person of ordinary skill in the art would expect the compounds to have similar properties and thus would contemplate making them to try and obtain compounds with improved properties.
As such, an artisan having ordinary skill in the art would have been motivated to modify one known element for another to predictably arrive at a compound of Formula (I):
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.
Regarding claim 2, Xue teaches L1 and L1’ are unsubstituted alkyl (page 2, Figure 1, Compound 3C).
Regarding claim 3, Xue teaches L1 and L1’ are C1-C10 alkyl (page 2, Figure 1, Compound 3C).
Regarding claim 4, Molt teaches R1a, R2a, R3a, R4a, R1a’, R2a’, R3a’, and R4a’ are absent (column 20, lines 55-65).
Regarding claim 5, Molt teaches
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(column 20, lines 55-65).
Regarding claim 6, Molt teaches R1, R3, R4, R1’, R3’, and R4’ are hydrogen (column 20, lines 55-65). Molt further teaches that R2 and R2’ are methyl; however, structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093- 95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers); In re Wilder, 563 F.2d 457, 460, 195 USPQ 426, 429 (CCPA 1977) (adjacent homologs and structural isomers); In re Hoch, 428 F.2d 1341, 1344, 166 USPQ 406, 409 (CCPA 1970) (acid and ethyl ester); In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring). Generally, some teaching of a structural similarity will be necessary to suggest selection of the claimed species or subgenus. The closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). See MPEP § 2144.08(II)(A)(4)(c). As the compound taught by the combination of Molt and Xue differs from the elected compound in the change from a methyl to a hydrogen (on the phenyl ring), a person of ordinary skill in the art would expect the compounds to have similar properties and thus would contemplate making them to try and obtain compounds with improved properties. Thus, Molt teaches the compound having R2 and R2a’ are hydrogen.
Regarding claim 7, Molt teaches
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(column 20, lines 55-65).
Regarding claim 8, Molt teaches A5, A5a’, A6, and A6’ are hydrogen:
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(column 20, lines 55-65).
Regarding claim 9, Molt teaches A5, A5a’, A6, and A6’ are hydrogen:
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(column 20, lines 55-65).
Regarding claim 10, Molt teaches that X1, X2, X3, X4, X1’, X2’, X3’, and X4’ are carbon (column 20, lines 55-65).
Regarding claim 13, Molt teaches R1, R3, R4, R1’, R3’, and R4’ are hydrogen (column 20, lines 55-65). Molt further teaches that R2 and R2’ are methyl; however, structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093- 95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers); In re Wilder, 563 F.2d 457, 460, 195 USPQ 426, 429 (CCPA 1977) (adjacent homologs and structural isomers); In re Hoch, 428 F.2d 1341, 1344, 166 USPQ 406, 409 (CCPA 1970) (acid and ethyl ester); In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring). Generally, some teaching of a structural similarity will be necessary to suggest selection of the claimed species or subgenus. The closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). See MPEP § 2144.08(II)(A)(4)(c). As the compound taught by the combination of Molt and Xue differs from the elected compound in the change from a methyl to a hydrogen (on the phenyl ring), a person of ordinary skill in the art would expect the compounds to have similar properties and thus would contemplate making them to try and obtain compounds with improved properties. Thus, Molt teaches the compound having R2 and R2a’ are hydrogen.
Regarding claim 14, Molt teaches R1, R3, R4, R1’, R3’, and R4’ are hydrogen (column 20, lines 55-65). Molt further teaches that R2 and R2’ are methyl; however, structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093- 95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers); In re Wilder, 563 F.2d 457, 460, 195 USPQ 426, 429 (CCPA 1977) (adjacent homologs and structural isomers); In re Hoch, 428 F.2d 1341, 1344, 166 USPQ 406, 409 (CCPA 1970) (acid and ethyl ester); In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring). Generally, some teaching of a structural similarity will be necessary to suggest selection of the claimed species or subgenus. The closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). See MPEP § 2144.08(II)(A)(4)(c). As the compound taught by the combination of Molt and Xue differs from the elected compound in the change from a methyl to a hydrogen (on the phenyl ring), a person of ordinary skill in the art would expect the compounds to have similar properties and thus would contemplate making them to try and obtain compounds with improved properties. Thus, Molt teaches the compound having R2 and R2a’ are hydrogen.
Regarding claim 43, the combination of Molt and Xue teaches the compound,
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(Molt: column 20, lines 55-65; Xue, page 2, Figure 1, Compound 3C).
10. Claims 1-10, 13-14, and 43 are rejected under 35 U.S.C. 103 as being unpatentable over Molt (U.S. Patent No. 9,108,998, issued 18 Aug 2015) in view of Volz (Adv. Mater., 2015, 27, 2538-2543) and Zhang (Angew. Chem. Int. Ed., 2022, 61(e202113718), 1-6).
Molt teaches dinuclear platinum-carbene complexes for OLEDs, such as
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(abstract; column 4, lines 50-65).
Molt specifically teaches
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(column 20, lines 55-65). Molt additionally teaches complexes that enable OLEDs to have long operative lifetime, good efficiency, high stability to thermal stresses, and a low use and operating voltage are of particular interest (column 1, lines 54-56). Molt further teaches that previous platinum-carbene complexes for OLEDs provided inadequate quantum yields with undesirable efficiency and stability (column 3, lines 1-5).
Molt fails to teach the compound,
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, having alkyl chain tying together the pyrazole and imidazole ligands (see reply to restriction requirement, filed 22 Jan 2026).
Volz teaches bridging ligands for dinuclear complexes in OLEDs (abstract). Volz specifically teaches the complex,
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, having alkyl ligands to reduce structural distortion (page 2539, column 1, paragraph 1; page 2539, column 2, paragraph 2). Volz additionally teaches that structural integrity of the molecule is of significant importance for its optoelectronic properties (page 2539, column 2, paragraph 2). Volz further specifies that molecular distortion upon excitation has to be suppressed, preferably by using multinuclear complexes with stable structural motifs, e.g. by use of fully bridging and chelating ligands (page 2542, column 2, paragraph 5).
Zhang teaches design of high-performance red and near-infrared OLEDs that are dinuclear platinum(II) complexes that utilize carboline as a bridging ligand (abstract). Zhang further teaches metallophilicity of d8 complexes is well-documented to generate highly radiative, lower-energy triplet metal-metal-to-ligand charge transfer (3MMLCT) excited states owing to the large parentage of ds* orbital in the highest occupied molecular orbital (page 1, column 2, paragraph 2). Zhang specifies that the use of rigid carboline as a bridge confines close Pt-Pt/pi-pi contacts and gives highly emission 3MMLCT states with relatively short emission lifetimes (page 4, column 2, paragraph 2).
It would have been prima facie obvious to one of ordinary skill in the art, prior to the effective filing date of the instantly claimed invention to employ alkyl chains of Volz and Zhang to rigidify the compounds of Molt to arrive at instant claim 1. One of ordinary skill in the art would have been motivated to make such a selection, with a reasonable expectation of success, because:
- Molt teaches dinuclear platinum-carbene complexes for OLEDs,
-Molt teaches
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,
-Molt teaches complexes that enable OLEDs to have long operative lifetime, good efficiency, high stability to thermal stresses, and a low use and operating voltage are of particular interest,
-Molt teaches previous platinum-carbene complexes for OLEDs provided inadequate quantum yields with undesirable efficiency and stability,
-Volz teaches bridging ligands for dinuclear complexes in OLEDs, such as the complex,
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, which has alkyl ligands to reduce structural distortion,
-Volz teaches that structural integrity of the molecule is of significant importance for its optoelectronic properties,
-Volz teaches that molecular distortion upon excitation has to be suppressed, preferably by using multinuclear complexes with stable structural motifs, e.g. by use of fully bridging and chelating ligands,
-Zhang teaches design of high-performance red and near-infrared OLEDs that are dinuclear platinum(II) complexes that utilize carboline as a bridging ligand,
-Zhang teaches metallophilicity of d8 complexes is well-documented to generate highly radiative, lower-energy triplet metal-metal-to-ligand charge transfer (3MMLCT) excited states owing to the large parentage of ds* orbital in the highest occupied molecular orbital, and
-Zhang teaches that the use of rigid carboline as a bridge confines close Pt-Pt/pi-pi contacts and gives highly emission 3MMLCT states with relatively short emission lifetimes.
Additionally, structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093- 95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers); In re Wilder, 563 F.2d 457, 460, 195 USPQ 426, 429 (CCPA 1977) (adjacent homologs and structural isomers); In re Hoch, 428 F.2d 1341, 1344, 166 USPQ 406, 409 (CCPA 1970) (acid and ethyl ester); In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring). Generally, some teaching of a structural similarity will be necessary to suggest selection of the claimed species or subgenus. The closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). See MPEP § 2144.08(II)(A)(4)(c). As the compound taught by the combination of Molt, Volz, and Zhang differs from the elected compound in the change from a methyl to a hydrogen (on the phenyl ring), a person of ordinary skill in the art would expect the compounds to have similar properties and thus would contemplate making them to try and obtain compounds with improved properties.
As such, an artisan having ordinary skill in the art would have been motivated to modify one known element for another to predictably arrive at a compound of Formula (I):
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.
Regarding claim 2, Volz teaches L1 and L1’ are unsubstituted alkyl (page 2539, column 1, paragraph 1; page 2539, column 2, paragraph 2).
Regarding claim 3, Volz teaches L1 and L1’ are C1-C10 alkyl (page 2539, column 1, paragraph 1; page 2539, column 2, paragraph 2).
Regarding claim 4, Molt teaches R1a, R2a, R3a, R4a, R1a’, R2a’, R3a’, and R4a’ are absent (column 20, lines 55-65).
Regarding claim 5, Molt teaches
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(column 20, lines 55-65).
Regarding claim 6, Molt teaches R1, R3, R4, R1’, R3’, and R4’ are hydrogen (column 20, lines 55-65). Molt further teaches that R2 and R2’ are methyl; however, structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093- 95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers); In re Wilder, 563 F.2d 457, 460, 195 USPQ 426, 429 (CCPA 1977) (adjacent homologs and structural isomers); In re Hoch, 428 F.2d 1341, 1344, 166 USPQ 406, 409 (CCPA 1970) (acid and ethyl ester); In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring). Generally, some teaching of a structural similarity will be necessary to suggest selection of the claimed species or subgenus. The closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). See MPEP § 2144.08(II)(A)(4)(c). As the compound taught by the combination of Molt, Volz, and Zhang differs from the elected compound in the change from a methyl to a hydrogen (on the phenyl ring), a person of ordinary skill in the art would expect the compounds to have similar properties and thus would contemplate making them to try and obtain compounds with improved properties. Thus, Molt teaches the compound having R2 and R2a’ are hydrogen.
Regarding claim 7, Molt teaches
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(column 20, lines 55-65).
Regarding claim 8, Molt teaches A5, A5a’, A6, and A6’ are hydrogen:
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(column 20, lines 55-65).
Regarding claim 9, Molt teaches A5, A5a’, A6, and A6’ are hydrogen:
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(column 20, lines 55-65).
Regarding claim 10, Molt teaches that X1, X2, X3, X4, X1’, X2’, X3’, and X4’ are carbon (column 20, lines 55-65).
Regarding claim 13, Molt teaches R1, R3, R4, R1’, R3’, and R4’ are hydrogen (column 20, lines 55-65). Molt further teaches that R2 and R2’ are methyl; however, structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093- 95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers); In re Wilder, 563 F.2d 457, 460, 195 USPQ 426, 429 (CCPA 1977) (adjacent homologs and structural isomers); In re Hoch, 428 F.2d 1341, 1344, 166 USPQ 406, 409 (CCPA 1970) (acid and ethyl ester); In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring). Generally, some teaching of a structural similarity will be necessary to suggest selection of the claimed species or subgenus. The closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). See MPEP § 2144.08(II)(A)(4)(c). As the compound taught by the combination of Molt, Volz, and Zhang differs from the elected compound in the change from a methyl to a hydrogen (on the phenyl ring), a person of ordinary skill in the art would expect the compounds to have similar properties and thus would contemplate making them to try and obtain compounds with improved properties. Thus, Molt teaches the compound having R2 and R2a’ are hydrogen.
Regarding claim 14, Molt teaches R1, R3, R4, R1’, R3’, and R4’ are hydrogen (column 20, lines 55-65). Molt further teaches that R2 and R2’ are methyl; however, structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093- 95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers); In re Wilder, 563 F.2d 457, 460, 195 USPQ 426, 429 (CCPA 1977) (adjacent homologs and structural isomers); In re Hoch, 428 F.2d 1341, 1344, 166 USPQ 406, 409 (CCPA 1970) (acid and ethyl ester); In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring). Generally, some teaching of a structural similarity will be necessary to suggest selection of the claimed species or subgenus. The closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). See MPEP § 2144.08(II)(A)(4)(c). As the compound taught by the combination of Molt, Volz, and Zhang differs from the elected compound in the change from a methyl to a hydrogen (on the phenyl ring), a person of ordinary skill in the art would expect the compounds to have similar properties and thus would contemplate making them to try and obtain compounds with improved properties. Thus, Molt teaches the compound having R2 and R2a’ are hydrogen.
Regarding claim 43, the combination of Molt, Volz, and Zhang teaches the compound,
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(Molt: column 20, lines 55-65; Volz: page 2539, column 1, paragraph 1; page 2539, column 2, paragraph 2; Zhang: page 4, column 2, paragraph 2).
Conclusion
No claim is allowed.
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/MADELINE M. DEKARSKE/ Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622