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 .
Terminal Disclaimer
The terminal disclaimer filed on 07/01/2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of Application no. 17/518,718 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Response to Amendment
The amendment of 01/23/2026 has been entered.
Disposition of claims:
Claims 2, 4, 12-15, 18, 23, 26-27 have been cancelled.
Claims 29 and 30 have been added.
Claims 1, 3, 5-11, 16-17, 19-22, 24-25, 28-30 are pending.
Claims 1, 11, 16, 19, and 28 have been amended.
The cancellation of claims 27-28 obviates the rejections of claims 27-28 set forth in the last Office Action.
The terminal disclaimer filed on 07/01/2026 obviates the provisional rejections of claims 1, 3, 5-6, 8-10, 16, 19-20 and 24-28 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 17, 20, and 28 of Application No. 17/518,718 (hereafter Application ‘718) set forth in the last Office Action.
The amendments of claims 1, 11, 16, 19, and 28 have overcome:
the rejections of claims 1, 3, 5-10, 16-17, 19-22, 25, and 27 under 35 U.S.C. 103 as being unpatentable over Takizawa et al. (US 2012/0153816, hereafter Takizawa) in view of Seo et al. (“High efficiency yellowish green phosphorescent emitter derived from phenylbenzothienopyridine ligand” Org. Elec. 2014, vol. 15, page 2068-2072, hereafter Seo), Wang et al. (“Highly efficient electroluminescent materials based on fluorinated organometallic iridium compounds”, Appl. Phys. Lett. 2001, Vol. 79, page 449-451, hereafter Wang), and Boudreault et al. (US 2016/0104848 A1, hereafter Boudreault ‘848) and
the rejections of claims 1, 3, 5-6, 8, 10-11, 16-17, 19-20, 24, and 27-28 under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2015/0236276 A1) in view of Takizawa et al. (US 2012/0153816), Wang et al. (“Highly efficient electroluminescent materials based on fluorinated organometallic iridium compounds”, Appl. Phys. Lett. 2001, Vol. 79, page 449-451), and Boudreault et al. (US 2016/0104848 A1) set forth in the last Office Action.
The rejections have been withdrawn.
Response to Arguments
Applicant’s arguments see page 15-18 of the reply filed 01/23/2026 regarding the rejections of claims 1, 3, 5-10, 16-17, 19-22, 25, and 27 under 35 U.S.C. 103 as being unpatentable over Takizawa/Seo/Wang/Boudreault ‘848 and the rejections of claims 1, 3, 5-6, 8, 10-11, 16-17, 19-20, 24, and 27-28 under 35 U.S.C. 103 as being unpatentable over Boudreault ‘276/Takizawa/Boudreault ‘848 set forth in the Office Action of 09/23/2025 have been considered.
Applicant argues that independent claims 1, 16, and 19 have been amended to include the subject matter of claim 26, which is not subject to this rejection such that the amended claims are patentable.
In the previous Office Action of 03/30/2026, the claim 26 was rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 17, 20, and 28 of Application No. 17/518,718 (hereafter Application ‘718) only, and no art rejection was applied. The Terminal Disclaimer of 07/1/2026 obviates the double patent rejections.
Upon further consideration, the Examiner found a prior art by Boudreault et al. (US 2016/0336520 A1, hereafter Boudreault ‘520) can be applicable to reject the previous claim 26. New grounds of rejection over Boudreault ‘520 are applied to reject the instant claims which includes the limitations of the previous claim 26. The amendment necessitates new grounds of rejection, making this Office Action final.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The 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.
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, 3, 5-11, 16-17, 19-22, 24-25 and 28-29 are rejected under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2016/0336520 A1, hereafter Boudreault ‘520).
Regarding claims 1, 3, 5-6, 8-11, 16-17, 19-20, 24 and 28-29, Boudreault ‘520 discloses a compound used as an emitter of an organic light emitting device ([0003]). The compound comprises a ligand LA of formula I wherein R is fused to ring B and has a structure of Formula II ([0016]-[0029]. Boudreault ‘520 exemplifies Compound 3676 ([0149]).
Boudreault ‘520 exemplifies an organic light emitting device (“Example 3” in [0173] and Table 4) comprising an anode (ITO), an organic layer (“emissive layer”) comprising Compound 3676 of Boudreault ‘520 as an emissive dopant and carbazole Compound H as a host, and a cathode (Al).
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The isopropyl group at the position corresponding to R4 of Formula II of Boudreault ‘520 is not a fluorinated cycloalkyl group; however, Boudreault ‘520 does teach that R4 can be a partially fluorinated cycloalkyl group ([0026]). Boudreault ‘520 exemplifies a substituent RA30,
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as the partially fluorinated cycloalkyl group ([0086]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skills in the art to have modified the Compound 3676 of Boudreault ‘520 by substituting the isopropyl group at the position corresponding to R4 of Formula II with a partially fluorinated cycloalkyl group RA30, as taught by Boudreault ‘520.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitutions of the exemplified substituent groups at the position corresponding to the R4 of the Formula II of Boudreault ‘520 in the compound of Boudreault ‘520 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified compound of Boudreault ‘520 (1).
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In the ligand Modified compound of Boudreault ‘520 (1), none of the CF3 groups is substituted to the position 1 of the cyclopentyl ring (i.e. see the annotated numbers in the figure above), which does not read on the limitation of the instant claims; however, Boudreault ‘520 does not restrict the substitution position of the fluorine atom in the partially fluorinated cycloalkyl group ([0077]), indicating that the CF3 group can be substituted to any carbon of the cycloalkyl group. Furthermore, Boudreault ‘520 exemplifies ligands (at least ligands RA1, RA3, RA6 in [0078]) having a CF3 group substituted to the position 1 of the alkyl groups. That is, Boudreault ‘520 exemplifies substitution position 1 for substituting a CF3 group.
Additionally, the Modified compound of Boudreault ‘520 (1) is one of position isomers with similar compounds in which the other position isomer, wherein the substitution position of one of CF3 groups (i.e. CF3 groups are substituted 1 and 2 substitution positions of the cyclopentyl group as shown in the figure below), meets the claim limitation.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Therefore, at the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to modify the Modified compound of Boudreault ‘520 (1) by changing the substitution position of one of CF3 groups such that the CF3 groups are substituted at the substitution positions 1 and 2 of the cyclopentyl group of the compound. A compound in which the substitution position of the CF3 group would represent a position isomer of the Modified compound of Boudreault ‘520 (1). One of ordinary skill in the art would expect that having each respective structure would act in similar manner.
The modification provides the Modified compound of Boudreault ‘520 (2) which has identical structure as the first compound of the instant claims, meeting all the limitations of claims 1, 3, 5-6, 8-11, and 28-29.
With respect to claim 24, the first aromatic ring (i.e. the ring A in the figure above) is indirectly fused to the ring (i.e. the dimethyl benzene ring D) that is coordinated to the metal, meeting all the limitations of claim 24.
The modification also provides Modified organic light emitting device comprising an anode (ITO), an organic layer (“emissive layer”) comprising Modified compound of Boudreault ‘520 (2) as an emissive dopant and carbazole Compound H as a host, and a cathode (Al), wherein the emissive layer materials are a composition, meeting all the limitations of claims 16-17 and 20.
Boudreault ‘520 does not exemplify a specific consumer product comprising the Modified organic light emitting device of Boudreault ‘520; however, Boudreault ‘520 does teach that the organic light emitting device can be incorporated in a consumer product ([0110]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skills in the art to have modified the Modified organic light emitting device of Boudreault ‘520 by incorporating it a consumer product, as taught by Boudreault ‘520.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, the substitutions of organic light emitting devices in a consumer product would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides a consumer product comprising the Modified organic light emitting device of Boudreault ‘520, meeting all the limitation of claim 19.
Regarding claim 7, the Modified compound of Boudreault ‘520 (2) reads on all the features of claim 1 as outlined above.
In the Modified compound of Boudreault ‘520 (2), the di-CF3-substituted cyclopentyl ring at the position corresponding to R4 of Formula II of Boudreault ‘520 does not have an alkylene (i.e. methylene) linker between the cyclopentyl group and thiophene ring; however, Boudreault ‘520 does teach that the substituent at the position R4 of Formula II of Boudreault ‘520 can be a combination of an alkyl and a partially fluorinated cycloalkyl ([0026]).
Boudreault ‘520 exemplifies several partially fluorinated alkyl groups wherein an alkylene group such as methylene is linking between the first aromatic ring and the partially fluorinated alkyl group (see examples in [0086], and compare RA3
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with RA14
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, and compare RA6
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with RA17
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).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skills in the art to have modified the Modified Compound of Boudreault ‘520 (2) by incorporating a methylene linker between the thiophene ring and the di-CF3-substituted cyclopentyl group, as taught by Boudreault ‘520.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, substitution of the substituent groups R4 of Boudreault ‘520 in the compound of Boudreault ‘520 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified compound of Boudreault ‘520 (3).
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Regarding claims 21-22, the Modified compound of Boudreault ‘520 (2) reads on all the features of claim 1 as outlined above.
In the Modified compound of Boudreault ‘520 (2), the di-CF3-substituted cyclopentyl ring at the position corresponding to R4 of Formula II of Boudreault ‘520 are not each a CHF2 group; however, Boudreault ‘520 does teach that the substituent at the position R4 of Formula II of Boudreault ‘520 can be a partially fluorinated cycloalkyl ([0026]).
Boudreault ‘520 exemplifies several partially fluorinated alkyl groups including CF3, CHF2, and CH2F (see examples in [0086], and compare RA3
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, RA4
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, and RA5
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).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skills in the art to have modified the Modified Compound of Boudreault ‘520 (2) by substituting the CF3 groups with CHF2 (or CH2F), as taught by Boudreault ‘520.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, substitution of the substituent groups R4 of Boudreault ‘520 in the compound of Boudreault ‘520 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified compound of Boudreault ‘520 (4).
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Regarding claim 25, Boudreault ‘520 discloses a compound used as an emitter of an organic light emitting device ([0003]). The compound comprises a ligand LA of formula I wherein R is fused to ring B and has a structure of Formula II ([0016]-[0029]. Boudreault ‘520 exemplifies Compound 3676 ([0149]).
Boudreault ‘520 exemplifies an organic light emitting device (“Example 3” in [0173] and Table 4) comprising an anode (ITO), an organic layer (“emissive layer”) comprising Compound 3676 of Boudreault ‘520 as an emissive dopant and carbazole Compound H as a host, and a cathode (Al).
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The isopropyl group at the position corresponding to R4 of Formula II of Boudreault ‘520 is not a fluorinated cycloalkyl group; however, Boudreault ‘520 does teach that R4 can be a partially fluorinated cycloalkyl group ([0026]). Boudreault ‘520 exemplifies a substituent RA38,
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as the partially fluorinated cycloalkyl group ([0086]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skills in the art to have modified the Compound 3676 of Boudreault ‘520 by substituting the isopropyl group at the position corresponding to R4 of Formula II with a partially fluorinated cycloalkyl group RA38, as taught by Boudreault ‘520.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitutions of the exemplified substituent groups at the position corresponding to the R4 of the Formula II of Boudreault ‘520 in the compound of Boudreault ‘520 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified compound of Boudreault ‘520 (5) which has identical structure as Compound 3676 except the isopropyl group at the position corresponding to R4 of Formula II of Boudreault ‘520 is substituted by CF3 substituted cyclohexyl group
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.
In the Modified compound of Boudreault ‘520 (5), the CF3-substituted cyclohexyl ring at the position corresponding to R4 of Formula II of Boudreault ‘520 is not a CH2F group; however, Boudreault ‘520 does teach that the substituent at the position R4 of Formula II of Boudreault ‘520 can be a partially fluorinated cycloalkyl ([0026]).
Boudreault ‘520 exemplifies several partially fluorinated alkyl groups including CF3, CHF2, and CH2F (see examples in [0086], and compare RA3
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, RA4
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, and RA5
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).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skills in the art to have modified the Modified Compound of Boudreault ‘520 (5) by substituting the CF3 groups with CHF2 (or CH2F), as taught by Boudreault ‘520.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Furthermore, substitution of the substituent groups R4 of Boudreault ‘520 in the compound of Boudreault ‘520 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified compound of Boudreault ‘520 (5).
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In the ligand Modified compound of Boudreault ‘520 (5), the CF3 group is not substituted to the position 1 of the cyclohexyl ring (i.e. see the annotated numbers in the figure above), which does not read on the limitation of the instant claims; however, Boudreault ‘520 does not restrict the substitution position of the fluorine atom in the partially fluorinated cycloalkyl group ([0077]), indicating that the CHF2 group can be substituted to any carbon of the cycloalkyl group. Furthermore, Boudreault ‘520 exemplifies ligands (at least ligands RA5 in [0078]) having a CHF2 group substituted to the position 1 of the alkyl groups. That is, Boudreault ‘520 exemplifies substitution position 1 for substituting a CHF2 group.
Additionally, the Modified compound of Boudreault ‘520 (5) is one of position isomers with similar compounds in which the other position isomer, wherein the substitution position of one of CHF2 groups (i.e. CHF2 group is substituted to position 1 of the cyclohexyl group as shown in the figure below), meets the claim limitation.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Therefore, at the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to modify the Modified compound of Boudreault ‘520 (5) by changing the substitution position of CHF2 groups such that the CHF2 group is substituted at the substitution position 1 of the cyclohexyl group of the compound. A compound in which the substitution position of the CHF2 group would represent a position isomer of the Modified compound of Boudreault ‘520 (5). One of ordinary skill in the art would expect that having each respective structure would act in similar manner.
The modification provides the Modified compound of Boudreault ‘520 (6) as shown above.
Claim 30 is rejected under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2016/0104848 A1) as applied to claims 1, 3, 5-11, 16-17, 19-22, 24-25 and 28-29 above, further in view of Edkins et al. (“Syntheses, Structures, and Comparison of the Photophysical Properties of Cyclometalated Iridium Complexes Containing the Isomeric 1- and 2-(2′-pyridyl)pyrene Ligands” Inorg. Chem. 2013, vol. 52, page9842-9860, hereafter Edkins).
Regarding claim 30, the Modified compound of Boudreault ‘520 (2) reads on all the features of claim 1 as outlined above.
In the Modified compound of Boudreault ‘520 (2), the dimethyl phenyl group at the position corresponding to the ring A of Formula I of Boudreault ‘520 is not pyrene; however, Boudreault ‘520 does teach that the ring A of Formula I can be a 6-membered carbocyclic ring ([0017]) and exemplifies pyrene as aromatic carbocyclic ring ([0053]).
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Edkins discloses a pyrene-containing Ir metal complex (Ir(2-pypyr)2(acac) in Scheme 1, Abstract). It is known in the art that Ir(ppy)2(acac) emits green light. Edkins teaches that Ir(2-pypyr)2(acac) emits red emission (Fig. 5), indicating that substitution of the phenyl ring of the phenyl pyridine-based ligand with pyrene, otherwise same, provides a red shift in the emission spectrum. Edkins further teaches that an Ir complex comprising 1-pypyr has unfavorable steric interaction and provides nonradiative deactivation (page 9858, column 2, line 3-6); thus, an ordinary skill in the art would choose 2-pypyr instead of 1-pypyr when forming a pyrene-containing Ir complex.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skills in the art to have modified the Modified Compound of Boudreault ‘520 (2) by substituting the dimethyl phenyl ring at the position corresponding to the ring A of Formula I of Boudreault ‘520 with 2-pyrene, as taught by Boudreault ‘520.
The motivation of doing so would have been to red shift the emission spectrum with reduced nonradiative deactivation, based on the teaching of Edkins.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the aromatic carbocyclic groups at the position corresponding to the ring A of Formula I of Boudreault ‘520 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified compound of Boudreault ‘520 (5), which has identical structure as the Modified compound of Boudreault ‘520 (2) except that the dimethyl phenyl group at the position corresponding to the ring A of Formula I of Boudreault ‘520 is replaced with 2-pyrene.
Conclusion
Applicant's amendment necessitated the 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 SEOKMIN JEON whose telephone number is (571)272-4599. The examiner can normally be reached Monday - Friday 8:30am to 5:00pm EST.
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/SEOKMIN JEON/Primary Examiner, Art Unit 1786