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 .
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.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 28 January 2026 has been entered.
Response to Amendment
The amendment of 28 January 2026 has been entered.
Disposition of claims:
Claims 1, 8-9, and 11 have been amended.
Claims 3 and 12 are cancelled.
Claims 21-22 are new.
Claims 1-2, 4-11, and 13-22 are pending.
The amendment to claim 1 has overcome the rejections of claims 1-3, 5-8, 10, and 13-20 under 35 U.S.C. 102(a)(2) as being anticipated by Hwang et al. (US 11,758,803 B2) (hereafter “Hwang ‘803”) set forth in the last Office action. The rejection has been withdrawn. However, as outlined below, new grounds of rejection have been made.
The amendment to claim 1 has overcome the rejections of claims 1-8 and 13-20 under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2013/0119354 A1) (hereafter “Ma ‘354”) in view of Ma et al. (US 2012/0217868 A1) (hereafter “Ma ‘868”) set forth in the last Office action as well as the rejection of claim 10 under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2013/0119354 A1) (hereafter “Ma ‘354”) in view of Ma et al. (US 2012/0217868 A1) (hereafter “Ma ‘868”) as applied to claim 1 above, and further in view of Li et al. (US 2002/0076576 A1) (hereafter “Li”) set forth in the last Office action. The rejections have been withdrawn. However, as outlined below, new grounds of rejection have been made.
The amendment to claim 1 has overcome the rejections of claims 1-3, 5-7, 9, 11, and 13-20 under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2016/0093816 A1) (hereafter “Ma ‘816”) in view of Ragini et al. (US 2006/0228582 A1) (hereafter “Ragini”) set forth in the last Office action. The rejections have been withdrawn. However, as outlined below, new grounds of rejection have been made.
Response to Arguments
Applicant’s arguments, see pp. 20-21 of the reply filed 28 January 2026, with respect to the rejections of claims 1-3, 5-8, 10, and 13-20 under 35 U.S.C. 102(a)(2) as being anticipated by Hwang et al. (US 11,758,803 B2) (hereafter “Hwang ‘803”) set forth in the last Office action have been fully considered and are persuasive. The rejections of claims 1-3, 5-8, 10, and 13-20 under 35 U.S.C. 102(a)(2) as being anticipated by Hwang et al. (US 11,758,803 B2) (hereafter “Hwang ‘803”) set forth in the last Office action have been withdrawn.
Applicant’s arguments with respect to the rejections of claims 1-8 and 13-20 under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2013/0119354 A1) (hereafter “Ma ‘354”) in view of Ma et al. (US 2012/0217868 A1) (hereafter “Ma ‘868”) set forth in the last Office action as well as the rejection of claim 10 under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2013/0119354 A1) (hereafter “Ma ‘354”) in view of Ma et al. (US 2012/0217868 A1) (hereafter “Ma ‘868”) as applied to claim 1 above, and further in view of Li et al. (US 2002/0076576 A1) (hereafter “Li”) set forth in the last Office action have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant’s arguments with respect to the rejections of claims 1-3, 5-7, 9, 11, and 13-20 under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2016/0093816 A1) (hereafter “Ma ‘816”) in view of Ragini et al. (US 2006/0228582 A1) (hereafter “Ragini”) set forth in the last Office action have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1-3, 5-8, 11, 13-15, and 21-22 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Lee et al. (US 12,448,403 B2) (hereafter “Lee”) .
The applied reference has a common Assignee, Applicant, and Joint Inventors with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2). This rejection under 35 U.S.C. 102(a)(2) might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C. 102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B) if the same invention is not being claimed; or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed in the reference and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement.
Regarding claims 1-3, 5-8, 11, 13-15, and 21-22: Lee discloses the compound shown below {col. 370, Table 84: Compound 2-163}.
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Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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.
Claim(s) 1-3, 5-8, 11, and 13-21 are rejected under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2020/0199163 A1) (hereafter “Tsai”) in view of Ragini et al. (US 2006/0228582 A1) (hereafter “Ragini”).
Regarding claims 1-3, 5-8, 11, 13-15, and 21: Tsai discloses the compound shown below {(paragraph [0051]: The compounds of the disclosure of Tsai comprise a ligand LX of Formula II.), (paragraph [0055]-[0057]: The ligands LX include the ligand LX6-4, which has the same structure as the ligand on the right side of the structural formula shown below.), (paragraphs [0058]-[0059]: The compounds can be an iridium complex and can additionally comprise a 2-phenylpyridine ligand.),(paragraph [0067] and p. 85, the compound shown below)}.
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Tsai teaches that the compounds of Tsai are useful as emissive dopants in the light emitting layer of an organic light emitting device {paragraphs [0068]-[0070]}.
Tsai does not exemplify a similar compound to the compound of Tsai shown above except for additionally comprising a silyl substituent on the 2-phenylpyridine ligands at the position equivalent to the instant X1.
Ragini teaches metal complex compounds having the structure shown below {paragraph [0016]}.
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Where in the structurally formula above rings CY1 and CY2 can each be aromatic rings and A^B is a monoanionic bidentate ligand {paragraph [0016]}. At least one of CY1, CY2, and A^B comprises a silyl substituent {paragraph [0016]}.
The compounds of Ragini are useful as phosphorescent light-emitting dopants in the light-emitting layer of organic light-emitting devices {abstract and paragraphs [0014]-[0015] and [0057]-[0060]}.
Ragini teaches that silyl substituted cyclometalated transition metal complexes have heat stability {paragraph [0029]}. Ragini exemplifies trimethylsilyl {paragraphs [0057]-[0060]}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the compound of Tsai shown above by substituting the compounds with a trimethylsilyl group, based on the teaching of Ragini. The motivation for doing so would have been to provide a metal complex having heat stability and efficient luminescence, as taught by Ragini.
Furthermore, it would have been obvious to have placed the substituent at the position equivalent to the instant X1, because it is one of the limited number of possible positions the substituent could be placed. The selection of the position equivalent to the instant X1 would represent one of a finite number of identified, predictable solutions—the possible places where the substituent could be placed—with a reasonable expectation of success. See MPEP 2143(I)(E). One of ordinary skill in the art would have been motivated to select suitable and optimum combinations of substituent and substituent positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
Regarding claims 16-20: Tsai as modified by Ragini teaches all of the features with respect to claim 1, as outlined above.
Claim 16 differs from claim 1 in that the claimed compound is comprised in an organic light emitting device.
Tsai does not exemplify a specific organic light-emitting device comprising the compound of Tsai shown above.
However, Tsai teaches an organic light-emitting device comprising a first electrode that is an anode, a second electrode that is a cathode, a hole transport region comprising a hole transport layer, and an electron transport region comprising an electron transport layer {Fig. 1 as well as paragraphs [0068]-[0070], [0082], [0086], [0089], and [0249]}.
Tsai teaches that the compounds of Tsai are useful as emissive dopants in the light emitting layer of an organic light emitting device {paragraphs [0068]-[0070]}.
The light emitting layer can additionally comprise a host material where the emissive dopant can be present at a concentration of 12% {paragraphs [0071] and [0249]}.
At the time the invention was effectively filed, it would have been obvious to one or ordinary skill in the art to have further modified the compound of Tsai by using it as a light emitting dopant of the light emitting layer of the light-emitting device of Tsai described above. The modification would have been a combination of prior art elements according to known methods to yield predictable results. See MPEP 2143(I)(A). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of materials to be used to make an organic light-emitting device in order to produce optimal organic light-emitting devices.
Regarding claim 20: Tsai as modified by Ragini teaches all of the features with respect to claim 16, as outlined above.
An organic light-emitting device is an electronic apparatus.
Claim(s) 10 is rejected under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2020/0199163 A1) (hereafter “Tsai”) in view of Ragini et al. (US 2006/0228582 A1) (hereafter “Ragini”) as applied to claim 1 above, and further in view of Li et al. (US 2002/0076576 A1) (hereafter “Li”).
Regarding claim 10: Tsai as modified by Ragini teaches all of the features with respect to claim 1, as outlined above.
Tsai as modified by Ragini does not exemplify a compound similar to the modified compound of Tsai except for the instant R12 not being hydrogen.
Li teaches electronic devices containing conjugated material wherein one or more hydrogens have been replaced with deuterium {abstract}. Li teaches that the materials that can be deuterated include Ir metal complexes {paragraph [0029]}. Li teaches that when deuterium is substituted for hydrogen on organic semiconductors compounds, the deuterated compounds possess improved thermal stability and longer lifetime in optoelectronic devices due to the stronger nature of the C-D bond relative to the C-H bond {p. 2, ¶ [0009], lines 11-13}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have further modified the device of Tsai such that the position equivalent to the instant R12 was deuterium rather than hydrogen, based on the teaching of Li. one of ordinary skill in the art would have been motivated to use materials that provide increased lifetime for the organic electroluminescent devices in which they’re used, based on the teachings of Li. Furthermore, it would have been obvious to have deuterated at least the position equivalent to the instant R12 would represent a finite number of possible positions for substitution of deuterium onto the compound of Ma ‘354 as modified by Ragini, with predictable results. See MPEP 2143(I)(E).
Claim(s) 1-2, 4-7, 9, 11, and 13-15 are rejected under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2013/0181190 A1) (hereafter “Ma ‘190”) in view of Ragini et al. (US 2006/0228582 A1) (hereafter “Ragini”) and Tsai et al. (US 2021/0054010 A1) (hereafter “Tsai ‘010”).
Regarding claims 1-2, 4-7, 9, 11, and 13-15: Ma ‘190 discloses the compound shown below {(paragraphs [0015], [0026], and [0046]: The compounds of the disclosure of Ma ‘190 have the structure of Formula I of Ma ‘190.), (paragraphs [0053], [0058], and [0117]: The compounds of the disclosure of Ma ‘190 can have the structure of the compound shown below)}.
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Ma ‘190 teaches that the compounds of Tsai are useful as emissive dopants in the light emitting layer of an organic light emitting device {paragraphs [0027] and [0061]}.
Ma ‘190 does not exemplify a similar compound to the compound of Ma ‘190 shown above except for additionally comprising a silyl substituent on the 2-phenylpyridine ligands at the position equivalent to the instant X1.
Ragini teaches metal complex compounds having the structure shown below {paragraph [0016]}.
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Where in the structurally formula above rings CY1 and CY2 can each be aromatic rings and A^B is a monoanionic bidentate ligand {paragraph [0016]}. At least one of CY1, CY2, and A^B comprises a silyl substituent {paragraph [0016]}.
The compounds of Ragini are useful as phosphorescent light-emitting dopants in the light-emitting layer of organic light-emitting devices {abstract and paragraphs [0014]-[0015] and [0057]-[0060]}.
Ragini teaches that silyl substituted cyclometalated transition metal complexes have heat stability {paragraph [0029]}. Ragini exemplifies trimethylsilyl {paragraphs [0057]-[0060]}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the compound of Ma ‘190 shown above by substituting the compounds with a trimethylsilyl group, based on the teaching of Ragini. The motivation for doing so would have been to provide a metal complex having heat stability and efficient luminescence, as taught by Ragini.
Furthermore, it would have been obvious to have placed the substituent at the position equivalent to the instant X1, because it is one of the limited number of possible positions the substituent could be placed. The selection of the position equivalent to the instant X1 would represent one of a finite number of identified, predictable solutions—the possible places where the substituent could be placed—with a reasonable expectation of success. See MPEP 2143(I)(E). One of ordinary skill in the art would have been motivated to select suitable and optimum combinations of substituent and substituent positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
Ma ‘190 does not exemplify a compound similar to the compound of Ma ‘190 in which a group that can be equated with the instant Z2 is a substituted or unsubstituted aryl group.
Tsai ‘010 teaches compounds that are useful as emitting dopants in the light-emitting layer of an organic light-emitting device {abstract as well as paragraphs [0096], [0104], [0124], and [0127]}.
Tsai ‘010 teaches iridium metal complexes having a similar structure to those of Ma ‘190 except for having a substituent at a position equivalent to the instant Z2, as shown by the structural formula shown below {paragraph [0053]}.
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Where A can be a five-membered or six-membered heterocyclic ring, and where D can be a 6-membered carbocyclic ring {paragraph [0053]}. Tsai ‘010 exemplifies unsubstituted biphenyl as D of Tsai ‘010 {paragraph [0168]}.
Tsai ‘010 teaches that the compounds of the disclosure of Tsai ‘010 can provide organic light-emitting devices having high efficiency and narrow FWHM {paragraph [0170]}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have further modified the compound of Ma ‘190 by substituting the dibenzofuran substructure of the compound of Ma ‘190 with an unsubstituted biphenyl group, based on the teaching of Tsai ‘010. The motivation for doing so would have been to produce a compound that can provide organic light-emitting devices having high efficiency and narrow FWHM, as taught by Tsai ‘010.
Conclusion
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/DYLAN C KERSHNER/ Primary Examiner, Art Unit 1786
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