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 Amendment filed, 26 May 2026. Claims 1, 3-7, 9-17, 19-26, 28, 33, 35-39, 41-42, and 48 are amended, and claim 34 is canceled. Claims 11-12, 15-33, 35-42, and 44-52 were previously withdrawn.
Claims 1-10, 13-14, and 43 are under consideration in the instant office action.
Information Disclosure Statement
The Information Disclosure Statements filed on 23 Feb 2026, 1 Apr 2026, 12 May 2026, and 2 June 2026 and the references cited therein have been considered, unless indicated otherwise.
Rejections Withdrawn
Claim Objections
1. Claims 10 and 13-14 were objected to for depending only upon claim 5 (which recites Formula IIa or IIb) but referencing a compound of Formula IIIa (claim 7). Claims 10 and 13-14 were amended to delete the reference to Formula IIIa. Applicant’s amendment, see pages 8-9, with respect to claims 10 and 13-14 has been fully considered. The claim objection of claims 10 and 13-14 has been withdrawn.
Claim Rejections – 35 U.S.C. § 112
2. Claims 1, 3, 5-6, and 13-14 were rejected for being indefinite and reciting a broad range together with a narrow range or limitation that falls within the broad range or limitation (in the same claim). Claims 1, 3, 5-6, and 13-14 were amended to delete the “preferably” and “such as” clauses. Applicant’s amendment, see pages 2-9, with respect to claims 1, 3, 5-6, and 13-14 has been fully considered. The rejection of claims 1, 3, 5-6, and 13-14 has been withdrawn.
3. Claims 1-10, 13-14, and 43 were rejected as being unpatentable under 35 U.S.C. 103 over Molt (U.S. Patent No. 9,108,998, issued 18 Aug 2015; of record, see PTO-892 mailed 24 Feb 2026) in view of Xue (Adv. Opt. Materials, 2022, 10(2200741), 1-9). Applicant’s amendment, see pages 26-35, with respect to claims 1-10, 13-14, and 43 has been fully considered. The rejection of claims 1-10, 13-14, and 43 has been withdrawn.
4. Claims 1-10, 13-14, and 43 were rejected as being unpatentable under 35 U.S.C. 103 over Molt (U.S. Patent No. 9,108,998, issued 18 Aug 2015; of record, see PTO-892 mailed 24 Feb 2026) in view of Volz (Adv. Mater.¸2018, 27, 2538-2543) and Zhang (Angew. Chem. Int. Ed., 2022, 61(e202113718), 1-6). . Applicant’s amendment, see pages 35-36, with respect to claims 1-10, 13-14, and 43 has been fully considered. The rejection of claims 1-10, 13-14, and 43 has been withdrawn.
Rejections New
Claim Rejections – 35 U.S.C. § 103
5. (New) Claims 1-10, 13-14, and 43 were rejected as being unpatentable under 35 U.S.C. 103 over Molt (U.S. Patent No. 9,108,998, issued 18 Aug 2015; of record, see PTO-892 mailed 24 Feb 2026) in view of Chen (Inorg. Chem., 2011, 50, 8671-8678) and Tagare (J. Mater. Chem.¸2021, 9, 4935-4947).
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 1-7). Molt teaches a blue diode having a CIE y-value of 0.21 (column 24, lines 26-29) and modulation of singlet and triplet states to tune for red and blue emitters through variations in ligands (column 1, lines 46-53; column 9, lines 42-51).
Regarding claim 1, Molt fails to teach
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(see reply to restriction requirement, filed 22 Jan 2026).
Chen teaches that pyrazole derivatives have adjacent nitrogen atoms that could incorporate more than one reactive metal atom in close proximity, thus facilitating potentially unique chemical reactivity and physical properties (page 8671, column 1, paragraph 1). Chen also teaches that many homo- or heterometallic complexes of pyrazole derivatives have found wide applications in material science and that metallocrowns involving N-heterocyclic carbene (NHC) ligands have not been known thus far (page 8671, column 1, paragraph 1; page 8671, column 2, paragraph 1). Chen teaches that NHCs have been extensively studied as ligands in organometallic chemistry due to the strong σ-donor properties and ease of preparation (page 8671, column 2, paragraph 2). Chen teaches that that multidentate NHCs have been used for construction of multinuclear metal complexes showing interesting optophysical properties (page 8671, column 2, paragraph 2). Chen specifically teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674).
Tagare teaches deep blue emitters with CIE y-values of 0.05 (abstract). Tagare teaches that the ever-increasing global energy crisis pushes the use of energy-efficient devices toward energy conservation efforts (page 4935, column 1, paragraph 1). Tagare teaches that the market for OLEDs has started to challenge other existing light sources because of their attractive features (e.g. simple fabrication processes, ultra-thin structures, light-weight, color tunability, flexibility, and possibilities of roll-to-roll manufacturing over large areas; page 4935, column 2, paragraph 1). Tagare teaches that current blue emitters have a higher efficiency and longer lifespan as compared to deep-blue emitters, but that ultra-blue emitters would be an integral part of white OLEDS for display applications to extra pure blue emission from white OLEDs (page 4935, column 2, paragraph 1). Tagare teaches that there are no ideal blue emitters currently based on phosphorescent metal complexes in terms of lifetime and stability, which limits the development of triplet emitter-based white OLEDs (page 4936, column 1, paragraph 1). Tagare teaches that a CIE y-value < 0.08 is still rare due to intrinsic wide-bandgap and that deep blue emitters could provide both superior color-gamut and reduced power consumption as well as exploited to create the light of other primary colors (page 4936, column 1, paragraph 1). Tagare teaches alkyl spacer-based emitters show ultra-deep-blue emission with superior device performance, such as PICFOCz and BICFOCz:
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(Figure 1, page 4936; page 4937, column 1, paragraph 2). Tagare teaches that PICFOCz and BICFOCz utilize a donor(carbazole)-acceptor (imidazole) strategy connected by a flexible alkyl spacer and have a CIE y-value of 0.05 (page 4936, Figure 1; page 4937, 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 modify
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of Molt to build an NHC metallocrown having CNN (also known as CCN) ligands as taught by Chen having a 5-carbon alkyl spacer as taught by Tagare to create a deep-blue emitter having a donor-acceptor design, because:
-Molt teaches dinuclear platinum-carbene complexes for OLEDs, such as
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,
-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 that previous platinum-carbene complexes for OLEDs provided inadequate quantum yields with undesirable efficiency and stability,
-Molt teaches a blue diode having a CIE y-value of 0.21 (column 24, lines 26-29) and modulation of singlet and triplet states to tune for red and blue emitters through variations in ligands,
-Chen teaches that pyrazole derivatives have adjacent nitrogen atoms that could incorporate more than one reactive metal atom in close proximity, thus facilitating potentially unique chemical reactivity and physical properties,
-Chen also teaches that many homo- or heterometallic complexes of pyrazole derivatives have found wide applications in material science and that metallocrowns involving N-heterocyclic carbene (NHC) ligands have not been known thus far,
-Chen teaches that NHCs have been extensively studied as ligands in organometallic chemistry due to the strong σ-donor porperties and ease of preparation,
-Chen teaches that that multidentate NHCs have been used for construction of multinuclear metal complexes showing interesting optophysical properties,
-Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand,
-Tagare teaches deep blue emitters with CIE y-values of 0.05,
-Tagare teaches that the ever-increasing global energy crisis pushes the use of energy-efficient devices toward energy conservation efforts,
-Tagare teaches that the market for OLEDs has started to challenge other existing light scources because of their attractive features (e.g. simple fabrication processes, ultra-thin structures, light-weight, color tunability, flexibility, and possibilities of roll-to-roll manufacturing over large areas),
-Tagare teaches that current blue emitters have a higher efficiency and longer lifespan as compared to deep-blue emitters, but that ultra-blue emitters would be an integral part of white OLEDS for display applications to extra pure blue emission from white OLEDs,
-Tagare teaches that there are no ideal blue emitters currently based on phosphorescent metal complexes in terms of lifetime and stability, which limits the development of triplet emitter-based white OLEDs,
-Tagare teaches that a CIE y-value < 0.08 is still rare due to intrinsic wide-bandgap and that deep blue emitters could provide both superior color-gamut and reduced power consumption as well as exploited to create the light of other primary colors,
-Tagare teaches alkyl spacer-based emitters show ultra-deep-blue emission with superior device performance, such as PICFOCz and BICFOCz:
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, and
-Tagare teaches that PICFOCz and BICFOCz utilize a donor(carbazole)-acceptor (imidazole) strategy connected by a flexible alkyl spacer and have a CIE y-value of 0.05.
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, Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674), wherein L1 and L1’ are unsubstituted alkyl. Additionally, Tagare teaches PICFOCz and BICFOCz:
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(Figure 1, page 4936; page 4937, column 1, paragraph 2), wherein L1 and L1’ are unsubstituted alkyl.
Regarding claim 3, Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674), wherein L1 and L1’ are C1-10 alkyl. Additionally, Tagare teaches PICFOCz and BICFOCz:
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(Figure 1, page 4936; page 4937, column 1, paragraph 2), wherein L1 and L1’ are C1-10 alkyl.
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), wherein X1, X2, X3, X4, X1’, X2’, X3’, and X4’ are carbon and R1, R3, R4, R1’, R3’, and R4’ are hydrogen. Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674), wherein L1 and L1’ are alkyl, and R2 and R2’ are hydrogen. Additionally, Tagare teaches PICFOCz and BICFOCz:
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(Figure 1, page 4936; page 4937, column 1, paragraph 2), wherein L1 and L1’ are alkyl. Thus, the combination of Molt, Chen, and Tagare teaches a compound of Formula (IIa).
Regarding claim 6, Molt teaches R1, R3, R4, R1’, R3’, and R4’ are hydrogen (column 20, lines 55-65). Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674), wherein R2 and R2’ are hydrogen. Accordingly, the combination of Molt and Chen teaches R1, R2, R3, R4, R1’, R2’, R3’, and R4’ are hydrogen.
Regarding claim 7, Molt teaches
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(column 20, lines 55-65), wherein A5, A6, A5’, and A6’ are hydrogen. Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674), wherein A5, A6, A5’, and A6’ are hydrogen. Additionally, Tagare teaches PICFOCz and BICFOCz:
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(Figure 1, page 4936; page 4937, column 1, paragraph 2), wherein L1 and L1’ are alkyl. Thus, the combination of Molt, Chen, and Tagare teaches a compound of Formula (IIIa).
Regarding claim 8, Molt teaches A5, A5a’, A6, and A6’ are hydrogen:
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(column 20, lines 55-65). Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674), wherein A5, A5a’, A6, and A6’ are hydrogen.
Regarding claim 9, Molt teaches A5, A5a’, A6, and A6’ are hydrogen:
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(column 20, lines 55-65). Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674), wherein A5, A5a’, A6, and A6’ are hydrogen.
Regarding claim 10, Molt teaches
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, wherein X1, X2, X3, X4, X1’, X2’, X3’, and X4’ are carbon (column 20, lines 55-65).
Regarding claim 13, Molt teaches
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, wherein R1, R3, R4, R1’, R3’, and R4’ are hydrogen (column 20, lines 55-65). Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674), wherein R2 and R2’ are hydrogen. Accordingly, the combination of Molt and Chen teaches R1, R2, R3, R4, R1’, R2’, R3’, and R4’ are hydrogen.
Regarding claim 14, Molt teaches
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, wherein R1, R3, R4, R1’, R3’, and R4’ are hydrogen (column 20, lines 55-65). Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674), wherein R2 and R2’ are hydrogen. Accordingly, the combination of Molt and Chen teaches R1, R2, R3, R4, R1’, R2’, R3’, and R4’ are hydrogen.
Regarding claim 43, Molt teaches
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(column 20, lines 55-65). Chen teaches the compound 6,
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, having CNN (also known as CCN) ligand (Scheme 4, page 8674). Additionally, Tagare teaches PICFOCz and BICFOCz:
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(Figure 1, page 4936; page 4937, column 1, paragraph 2) having a 5-carbon alkyl spacer between the donor and acceptor ligands. Accordingly, the combination of Molt, Chen, and Tagare teaches
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.
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
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