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 .
Response to Amendment
In the response filed 01/22/2026, the claims and specification were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the specification, the objection the specification is withdrawn by the Office.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 112(b) of claims 8, 10-13, 15, 17-18, and 24-25 is withdrawn by the Office.
Claims 1, 3, 4, 8-15, 17, 18, 24, and 25 have been amended.
Claims 27-29 have been added.
Claims 1-29 are pending in the application.
Response to Arguments
Applicant's arguments have been fully considered but they are not persuasive.
With respect to Applicant’s argument that, based on the examples of the instant description, the ordinary skill artisan would expect a moiety of Formula 4 to result in higher efficiency and lower driving voltage, Examiner agrees.
This is taught by Yamamoto in paragraph [0012], which states that an iridium complex with a divalent ligand can result in remarkably increased durability and lowered driving voltage of an organic electroluminescent element when the ligand comprises a moiety with 3 or more fused rings as a substituent. Such a substituent is analogous to instant Formula 4. As driving voltage has a direct effect on efficiency of an organic electroluminescent device, a person having ordinary skill in the art would expect the current efficiency, power efficiency, and external quantum efficiency would be increased as a result of the lowered driving voltage. Thus, these effects do not represent unexpected results.
With specific regard to Group II and the comparison of Metal complex 867 and GD2, a diarylamino substituent is not required by the instant claims nor used in the rejection of record.
With respect to Applicant’s argument that Cai should not be modified by Yamamoto because Cai encompasses a different inventive concept, Examiner disagrees.
There is no teaching in Cai nor reason to believe that adding the substituent with 3 or more rings described by Yamamoto would render the compound of Cai inoperable (MPEP 2143.01). Particularly because Cai teaches that the outer benzene group of the dibenzoheterole moiety can bear a wide variety of substituents including a C12 heteroaryl group (see for example Formulae 2 through 9 on page 18 and the definition of R4 in paragraph 0105). Further, there are only three open valences on the outer benzene group, so a very limited number of combination possibilities are present (MPEP 2131.02).
With respect to Applicant’s argument that Cai is silent to the link being to the 9-position of a carbazole moiety, Examiner agrees.
The 9-carbazole linking group is taught by Yamamoto and exemplified through compounds on pages 21-23 and 39-40 of the prior art.
With respect to Applicant’s argument that the invention of claim 1 has an unexpected technical effect over Cai, Examiner disagrees.
In paragraph [0012] of Yamamoto, Yamamoto teaches that an iridium complex with a divalent ligand can result in remarkably increased durability and lowered driving voltage of an organic electroluminescent element when the ligand comprises a moiety with 3 or more fused rings as a substituent. Such a substituent is analogous to instant Formula 4. As driving voltage has a direct effect on efficiency of an organic electroluminescent device, a person having ordinary skill in the art would expect the current efficiency, power efficiency, and external quantum efficiency would be increased as a result of the lowered driving voltage. Thus, these effects do not represent unexpected results.
With respect to Applicant’s argument that the teaching of Yamamoto cannot be applied to Cai because they differ in the skeleton structure of the divalent ligand, Examiner disagrees.
Yamamoto is clear that the effect of lowered driving voltage is a result of the substituent rather than the effect of the combination of the ligand and the substituent.
Yamamoto teaches that use of the extended pi-conjugation system having 3 or more fused rings makes it possible to improve the charge transporting property (of holes and electrons) or improve the stability for charges (holes and electrons) by stabilization of a radical cation state and a radical anion state, thus improving the durability and driving voltage of an organic electroluminescent element (paragraph 0053).
For at least these reasons, the rejection over Cai in view of Yamamoto is respectfully maintained.
However, Applicant’s amendments have necessitated a reinterpretation of the art as set forth below to explain how the prior art still reads on the claimed invention.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
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.
Claims 1-29 are rejected under 35 U.S.C. 103 as being unpatentable over Cai et al. (US 2020/0091442 A1) and further in view of Yamamoto et al. (US 2014/0306205 A1).
With respect to claim 1, Cai discloses compound Ir(La107)(Lb1)2, which is pictured below (page 40).
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This compound is derived from Cai formula 2 (page 18), which is pictured below.
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In this formula, Cai also teaches that R4 is a substituted or unsubstituted heteroaryl group having 12 carbon atoms (paragraph 0105, lines 13-14), and examples of heteroaryl groups include carbazole (paragraph 0060, line 9).
Such a modification produces a compound that meets the requirements of instant Formula 1 when M is iridium, Cy is an unsubstituted heteroaromatic ring having 6 ring atoms (pyridine), Cy is joined to M via a metal-nitrogen bond, X is oxygen, X1 is a carbon atom joined to Cy, X2 is a carbon atoms joined to M, X3 --through X6- are CRx wherein Rx is a hydrogen atom, X7 is CRx wherein Rx is a halogen (fluorine) atom, and X8 is CRx1 wherein Rx1 is represented by Formula 4. In Formula 4, A3 to A6 are CRA and each RA is a hydrogen atom, B3 to B6 are CRB and each RB is a hydrogen atom, n is 1 and L is a single bond and Formula 4 forms an unsubstituted carbazole moiety.
Cai includes each element claimed, with the only difference between the claimed invention and Cai being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a metal complex with a fluorine substituent which shows features of longer device lifetime, better thermal stability, and no blue-shifted emission (paragraph 0011), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, while within the scope of Cai, Cai does not teach nor fairly suggest a moiety of instant Formula 4 as a substituent.
In analogous art, Yamamoto teaches an electroluminescent element having high durability which is provided by an iridium metal complex with a substituent group G which comprises a fused ring with 3 or more rings (abstract).
Yamamoto teaches that preferred examples of substituent G include 9-carbazole (third formula of paragraph 0025 and paragraph 0112, line 2).
Yamamoto teaches that an iridium complex having divalent ligands can remarkably increase the durability of an organic electroluminescent element and lower driving voltage when used as an element by having 1 or 2 ligands having 3 or more fused rings as an additional substituent (paragraph 0012).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use a 9-carbazole as a substituent on the organometallic compound of Cai in order to obtain a compound which can remarkably increase the durability and lower the driving voltage of an electroluminescent device comprising the compound, as taught by Yamamoto.
With respect to claim 2, Cai and Yamamoto teach the metal complex of claim 1, and ring Cy is a pyridine ring, which is the sixth embodiment of the instant claim, as pictured and discussed above.
With respect to claim 3, Cai and Yamamoto teach the metal complex of claim 1, and the metal complex has the formula of Ir(LA)(LB)2 wherein M is iridium, m is 1, n is 2, q is 0, and Lc is not present, and La is selected as the seventeenth embodiment of the claim, which is pictured below.
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Similarly, LB is a phenylpyridine ligand as pictured above, which is the sixth embodiment of the instant claim when Ra and Rb represent no substitution.
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All other variables are the same as discussed above.
With respect to claim 4, Cai and Yamamoto teach the metal complex of claim 1, and the metal complex has the structure of Ir(LA)(LB)2 wherein m is 1, Y1 to Y4 are each CR wherein all R variables represent a hydrogen atom, and all other variables are the same as discussed above.
With respect to claim 5, Cai and Yamamoto teach the metal complex of claim 4, and X1 is a carbon atom joined to Cy, X2 is a carbon atom joined to M, X3 --through X6- are CRx wherein Rx is a hydrogen atom, X7 is CRx wherein Rx is a halogen (fluorine) atom, and X8 is CRx1 wherein Rx1 is represented by Formula 4 and Y1 to Y4 are each CR wherein all R variables represent a hydrogen atom, as discussed above.
With respect to claim 6, Cai and Yamamoto teach the metal complex of claim 4, as discussed above.
Cai Formula 2 is derived from the more broad Formula 1, which is pictured below.
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Cai also teaches that any of X1 through X7 can be a nitrogen atom (paragraph 0018).
Such a modification produces a compound that meets the requirements of the instant claim when one of X3 to X8 is a nitrogen atom.
Cai includes each element claimed, with the only difference between the claimed invention and Cai being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a metal complex with a fluorine substituent which shows features of longer device lifetime, better thermal stability, and no blue-shifted emission (paragraph 0011), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 7, Cai and Yamamoto teach the metal complex of claim 4, and X is an oxygen atom, as discussed above.
With respect to claim 8, Cai and Yamamoto teach the metal complex of claim 4, and each Rx is a hydrogen atom or a halogen atom, as discussed above.
With respect to claims 9-11, Cai and Yamamoto teach the metal complex of claim 1, and Rx1 has the structure of Formula 4 when all A variables are CRA and all B variables are CRB and all RA and RB are hydrogen atoms, n is 1 and L is a single bond, as pictured above.
With respect to claim 12, Cai and Yamamoto teach the metal complex of claim 1, and X8 is CRx1, as discussed above.
With respect to claim 13, Cai and Yamamoto teach the metal complex of claim 1 and X7 is CRx wherein Rx is a fluorine atom and X8 is CRx1 wherein Rx1 is a carbazole, as discussed above.
With respect to claim 14, Cai and Yamamoto teach the metal complex of claim 3, and Rx1 is selected as An1, as discussed above.
With respect to claim 15, Cai and Yamamoto teach the metal complex of claim 4 and all R variables represent a hydrogen atom, as discussed above.
With respect to claims 16 and 17, Cai and Yamamoto teach the metal complex of claim 4, as discussed above.
Cai also teaches that the ancillary ligand Lb may be selected as Lb13 (paragraph 0108), which is pictured below.
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Such a modification produces a compound that meets the requirements of the instant claim wherein R2 and R6 are an alkyl group of 1 carbon atom (methyl).
With respect to claim 18, Cai and Yamamoto teach the metal complex of claim 14, and La is selected as La1020 wherein Cy is Cy1, RX7 is F, RX8 is An1 and X is oxygen, and all other variables are hydrogen atoms.
With respect to claim 19, Cai and Yamamoto teach the metal complex of claim 18, and Lb is instant Lb1, as pictured above.
With respect to claim 20, Cai and Yamamoto teach the metal complex of claim 19, and Lc is not present, as discussed above.
With respect to claim 21, Cai and Yamamoto teach the metal complex of claim 20, and the metal complex is instant metal complex 143.
With respect to claims 22 and 23, Cai and Yamamoto teach the metal complex of claim 1, and Cai also teaches an electroluminescent device comprising an anode, a cathode, and an organic layer (paragraph 0113), and the organic layer comprises an emission layer and the emission layer comprises the metal complex (abstract).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to include the compound in the emissive layer of an electroluminescent device with the claimed device structure, as taught by Cai.
With respect to claims 24 and 25, Cai and Yamamoto teach the metal complex of claim 23, and Cai teaches that the emissive layer further comprises at least two hosts (paragraph 0123, lines 1-4) and the host may comprise a carbazole moiety (see the example host materials on page 31), and Cai gives the composition of the emission layer of example devices in Table 1, and they comprise a 46:46:8 ratio of the first host: second host: dopant (see also paragraph 0191).
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). Similarly, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 783, 227 USPQ 773, 779 (Fed. Cir. 1985). See MPEP 2144.05 Obviousness of Similar and Overlapping Ranges, Amounts, and Proportions. In the instant case, the weight percent of the instant claims overlap in scope with the weight percent of the prior art. Thus, as the ranges overlap, a prima facie case of obviousness is present.
With respect to claim 26, Cai and Yamamoto teach the metal complex of claim 1, and Cait also teaches that each layer described may comprise a mixture of multiple materials (paragraph 0041), which implies the existence of a composition comprising the metal complex.
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to create a composition comprising the metal complex in order to obtain a mixture for manufacturing the emission layer of the device, as taught by Cai.
With respect to claims 27 and 29, Cai and Yamamoto teach the metal complex of claim 1, and X3 --through X6- are CRx wherein Rx is a hydrogen atom, X7 is CRx wherein Rx is a halogen (fluorine) atom, and X8 is CRx1 wherein Rx1 is represented by Formula 4
With respect to claim 28, Cai and Yamamoto teach the metal complex of claim 1, and RA and RB are each hydrogen atoms.
Conclusion
Applicant's amendment necessitated any new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached at 571-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/RACHEL SIMBANA/Examiner, Art Unit 1786
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