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 .
DETAILED ACTION
Claim Objections
Claim 1 is objected to. The limitation “asterix” should be corrected to “asterisk”.
Claim 1 is further objected to. The limitation “R1 and R5 (if present) are independently selected from CN, CF3, halogen, Cl, F, H, or D” should be amended to “R1 and R5 (if present) are independently selected from the group consisting of CN, CF3, Cl, F, H, and D” or alternatively to “R1 and R5 (if present) are independently selected from the group consisting of CN, CF3, halogen, H, and D”.1
Claim 1 is further objected to. The limitation “R2, R3, and R4 (if present) are independently selected from CN, partially fluorinated or perfluorinated C1 to C8 alkyl, halogen, Cl, F, H, or D” should be amended to “R2, R3, and R4 (if present) are independently selected from the group consisting of CN, partially fluorinated or perfluorinated C1 to C8 alkyl, halogen, H, and D” or alternatively to “R2, R3, and R4 (if present) are independently selected from the group consisting of CN, partially fluorinated or perfluorinated C1 to C8 alkyl, Cl, F, H, and D”.1
Claim 1 is further objected to. The limitation “Ar are independently selected from CN, partially or perfluorinated C1 to C6 alkyl, halogen, Cl, F, D;” should be amended to “Ar are independently selected from the group consisting of CN, partially fluorinated or perfluorinated C1 to C6 alkyl, halogen, and D” or alternatively to “Ar are independently selected from the group consisting of CN, partially fluorinated or perfluorinated C1 to C6 alkyl, Cl, F, and D”.1
Claim 1 is further objected to. The limitation “R‘ is selected from Ar, substituted or unsubstituted C6 to C18 aryl or C3 to C18 heteroaryl, partially fluorinated or perfluorinated C1 to C8 alkyl, halogen, F or CN” should be amended to “R‘ is selected from the group consisting of Ar, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C18 heteroaryl, partially fluorinated or perfluorinated C1 to C8 alkyl, halogen, and CN” or alternatively, “R‘ is selected from the group consisting of Ar, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C18 heteroaryl, partially fluorinated or perfluorinated C1 to C8 alkyl, F, and CN”.1
Claim 2 is objected to. The limitation “The compound of claim 1, selected of the formula (IV)” is grammatically unconventional and should be amended to “The compound of claim 1, selected from formula (IV)”.
Claim 4 is objected to. The limitation “present and independently selected” should be amended to “present and are independently selected” for better clarity.
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.
Claims 1-6 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. A broad limitation together with a narrow limitation that falls within the broad 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). Independent claim 1 recites three instances where a broad recitation “halogen” is followed by the narrower recitation “Cl, F”. Additionally, claim 1 recites an instance where a broad recitation “halogen” is followed by the narrower recitation “F”. The claims 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. In order to overcome this rejection, Applicants should amend all instances above to either exclude “halogen” or to exclude “Cl or F” or “F” where necessary. Claims 2-6 are included in this rejection as they depend from rejected claim 1.
Claim 7 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 7, which is written as an independent claim, recites the limitation that the organic semiconductor layer comprises a compound of formula (IV). However, formula (IV) is not defined anywhere in claim 7, rendering the claim indefinite. For purposes of further examination, claim 7 will be interpreted as being dependent on claim 2, which does recite formula (IV).
Claim 12 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 12 is dependent on claim 11, which is dependent on claim 9, which is dependent on claim 8, which is dependent on claim 1. Claim 12 recites the limitation “the p-type charge generation layer”. However, this limitation lacks proper antecedent basis as it is not recited in any of claims 1, 8, 9, or 11. To overcome this rejection, the Examiner suggests amending claim 11 to be dependent on claim 10, which does include the limitation “p-type charge generation layer”.
Claim 13 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 13 is dependent on claim 11, which is dependent on claim 9, which is dependent on claim 8, which is dependent on claim 1. Claim 13 recites the limitation “the p-type charge generation layer”. However, this limitation lacks proper antecedent basis as it is not recited in any of claims 1, 8, 9, or 11. To overcome this rejection, the Examiner suggests amending claim 11 to be dependent on claim 10, which does include the limitation “p-type charge generation layer”.
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 of this title, 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.
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 1-9, 11, 14 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Hummert et al. (US 2017/0373251).
Claim 1: Hummert et al. teaches substituted 1,2,3-triylidenetris(cyanomethanylidene) cyclopropanes (referred to as [3]-radialene compounds) which adhere to general formula (1) as taught in paragraph 0017. Hummert et al. further teaches that A1 and A2 are selected from 11 specific aryl and/or heteroaryl groups with at least one of the aryl or heteroaryl groups being selected from 9 specific aryl or heteroaryl groups (paragraph 0017). Formula (I) further includes embodiments where the two A1 groups are different from the A2 group. Formula (I) as recited in independent claim 1 requires that variable A1 is equal to a group of formula (II), variable A2 is equal to a group of formula (III) and variable A3 is equal to a group of formula (II) or formula (III). Variable R’ in formulae (II) and (III) of claim 1 includes CN, which is the group employed in all of the compounds taught by Hummert et al. Formula (II) of claim 1 also requires at least one of X1 or X5 to be equal to CR1 or CR5, respectively, with R1 and/or R5 equal to a CN group or a CF3 group. Variable Ar in formula (III) is a substituted aryl or heteroaryl group which is required to have at least one group selected from CN, partially fluorinated or perfluorinated C1-C6 alkyl, halogen, and deuterium.
While none of the explicitly taught asymmetric compounds B1 through B10 satisfy all of the structural limitations of claim 1, it is submitted that the overall teachings of Hummert et al. render obvious to a person having ordinary skill in the art the preparation of compounds which satisfy all of the structural limitations of claim 1. Specifically, as mentioned above, paragraph 0017 of Hummert et al. teaches that A1 and A2 are selected from 11 specific aryl and/or heteroaryl groups with at least one of the aryl or heteroaryl groups being selected from 9 specific aryl or heteroaryl groups (paragraph 0017). Included in the 9 specific aryl or heteroaryl groups of Hummer et al. is 3,4-dicyano-2,5,6-trifluorphenyl which satisfies the condition in formula (III) that Ar is substituted by at least two CN groups. The groups 2,4-bis(trifluoromethyl)-3,5,6-trifluorophenyl, 2,5-bis(trifluoromethyl)-3,4,6-trifluorophenyl, 2,4,6-tris(trifluoromethyl)-1,3-diazine-5-yl, and 2-cyano-3,5,6-trifluoropyridine-4-yl satisfy all of the limitations of formula (II) as they all include at least one CR1 or CR5 groups where R1 or R5 is equal to CN or CF3. Given the small number of explicitly taught groups and the teaching that A1 and A2 may be different from each other, one having ordinary skill in the art would have found it obvious to have selected any one of the 11 groups recited in paragraph 0017 as A1 or A2 and any one of the 9 required groups recited in paragraph 0017 as the other of A1 or A2. For example, selecting both A1 to be 2,4-bis(trifluoromethyl)-3,5,6-trifluorophenyl and selecting A2 to be 3,4-dicyano-2,5,6-trifluorophenyl or selecting both A1 to be 3,4-dicyano-2,5,6-trifluoropropyl and selecting A2 to be 2,4-bis(trifluoromethyl)-3,5,6,-trifluoropropyl are both obvious selections from the small number of possible selections disclosed in paragraph 0017. Such compounds have the structures
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and
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, respectively. As applied to formula (I) of claim 1, the above compounds have as A1, a group where R’ is CN, X1-X5 are CR1-CR5 with R1 equal to CF3 and R2-R5 equal to F, and have as A2, a group where R’ is CN, Ar is a substituted C6 aryl group which has, as substituents, three fluoro and two cyano groups. Group A3 can refer to either of A1 or A2 above.
Additionally, the selection of both A1 to be 2,4,6-tris(trifluoromethyl)-1,3-diazine-5-yl and selecting A2 to be 3,4-dicyano-2,5,6-trifluorophenyl or selecting both A1 to be 3,4-dicyano-2,5,6-trifluoropropyl and selecting A2 to be 2,4,6-tris(trifluoromethyl)-1,3-diazine-5-yl are both obvious selections from the small number of possible selections disclosed in paragraph 0017. Such compounds have the structures
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and
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. As applied to formula (I) of claim 1, the above compounds have as A1, a group where R’ is CN, X1-X5 are CR1-CR5 with R1, R3, and R5 equal to CF3 and X2 and X4 equal to N, and have as A2, a group where R’ is CN, Ar is a substituted C6 aryl group which has, as substituents, three fluoro and two cyano groups. Group A3 can refer to either of A1 or A2 above. Further, asymmetric compound B1 includes, as a substituent 2,4,6-tris(trifluoromethyl)-1,3-diazine,5-yl and asymmetric compound B2 includes, as a substituent, 3,4-dicyano-2,5,6-trifluorophenyl. Combining the various substituents from B1 and B2 affords compounds as shown directly above.
One having ordinary skill would have been motivated to prepare additional compounds, including those shown above, as the number of explicitly taught groups for A1 and A2 is relatively small and further exploration of combinations from the finite list of choices of A1 and A2 provides alternative embodiments which would be expected to perform predictably given the teachings of Hummert et al.
Claim 2: The four compounds shown directly in claim 1 above satisfy formula (IV) of claim 2 with B1 being 3,4-dicyano-2,5,6-trifluorophenyl which satisfies formula (V) of claim 2 as described in claim 1 above, and one or two of B3 and B5 being selected from the groups shown in the structures above where one of B3 and B5 may be the same as B1.
Claim 3: The four compounds above have six CN groups, which satisfies claim 3.
Claim 4: The second set of two compounds shown above in claim 1 have both R1 and R5 equal to CF3, which satisfies claim 4.
Claim 5: In all compounds taught by Hummert et al., R‘ is equal to CN, thereby satisfying claim 5.
Claim 6: In the four compounds shown in claim 1 above, Ar comprises two adjacent groups, thereby satisfying claim 6.
Claim 7: Claim 7 is drawn to a composition comprising a compound of formula (IV) as recited in claim 2 above and at least one compound of formulae (IVa) to (IVd). The compounds of formulae (IVa) to (IVd) represent different possible geometrical isomers formed by various combinations of E- and Z-substitution on the three exocyclic double bonds of the [3]-radialene. In paragraph 0031, Hummert et al. explicitly teaches that while the exemplified structures are shown as having one geometric configuration, the materials synthesized by the described methods may comprise all possible geometric isomers. As shown in the preparation of radialene compound B7 as one example (paragraph 0135), the penultimate product is a compound having a cyclopropane moiety with two single bonds attached thereto. The single bonds allow for at least some rotation about the single bond axis so that during the acid treatment step, various geometric isomers are formed. While separation of said isomers may be carried out, the crude reaction mixtures would comprise multiple geometric isomers. Indeed, the reaction yield for radialene B7 is taught as being 30%, indicative that 70% of the final reaction products are not compound B7. One having ordinary skill in the art would have therefore expected that in the preparation of any one of the four compounds shown in claim 1 above, a crude reaction mixture would be present which comprises at least one other geometric isomer. Such a crude reaction mixture satisfies claim 7.
Claims 8 and 9: The radialene compounds taught by Hummert et al. are taught to be employed as p-dopants in hole injection layers of organic electroluminescent devices. An exemplified device is taught in paragraph 0139. The exemplified device includes an anode, a hole injection layer comprising a matrix material and a p-dopant which is a [3]-radialene compound as taught therein, an emission layer, an electron transport layer, an electron injection layer, and a cathode. This device architecture also satisfies the device limitations of claim 9.
Claim 11: The exemplified device of Hummert et al. includes a hole injection layer, thereby satisfying claim 11.
Claim 14: The exemplified device of Hummert et al. is an electroluminescent device, thereby satisfying claim 14.
Claim 15: Being a light-emitting device, the exemplified device of Hummert et al. qualifies as a display device as it emits light for display, thereby satisfying claim 15.
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Hummert et al. (US 2017/0373251), further in view Jankus et al. (US 2017/0346023).
Hummert et al. teaches in paragraph 0009 that the compounds of formula (I) are employed as hole injection or charge generation materials. While Hummert et al. does not explicitly teach employing any one of the radialene compounds of formula (I) as described therein as a p-type charge generation material, it would have been obvious to one having ordinary skill in the art given the teachings of Jankus et al. Hummert et al. and Jankus et al. are combinable as they are both from the same field of organic electroluminescent devices. One having ordinary skill in the art understands that the role of a charge generation layer is to act as a p-n junction which separates two light-emitting units in a stacked/tandem light-emitting device. Jankus et al. represents one such teaching. Fig.4 of Jankus et al. is drawn to a tandem light-emitting device comprising an anode, a first hole transport region a first emission region, a first electron transport region, a charge generation region comprising a p-type and an n-type charge generation layer, a second hole transport region, a second emission region, a second electron transport region, and a cathode (paragraph 0246). Jankus et al. teaches that the charge generation layer is a double layer, that is, the charge generation layer is comprised of a n-type charge generation layer and a p-type charge generation layer (paragraph 0195). Jankus et al teaches that the pn junction created by these adjacent n-type and p-type layer generated charges or separates holes and electrons with the n-type charge generation layer providing electrons for the first light emitting layer and the p-type charge generation layer providing holes for the second light emitting layer. This architecture improves luminous efficiency and reduces the driving voltage of the organic light emitting diode as taught in paragraph 0195. Additionally, Jankus et al. teaches that the p-type charge generation layer may comprise a radialene derivative (paragraph 0197). Given these teachings, it would have been obvious to one having ordinary skill in the art to have employed the radialene compounds as taught by Hummert et al. in a charge generation layer as disclosed by Hummert et al., more specifically in a p-type charge generation layer the motivation being rooted in the teachings of Jankus et al., thereby satisfying claim 10.
Claims 11 and 122: The devices of Hummert et al. includes a hole injection layer, which satisfies claim 11. While Hummert et al. does not explicitly teach that the hole injection layer and charge generation layer comprise the same compound of formula (I), it would have been obvious to one having ordinary skill in the art given the teachings of Hummert et al. and Jankus et al. Specifically, Hummert et al. teaches that radialene compounds are employed in both hole injection and charge generation layers (paragraph 0009). Jankus et al. provides motivation for one having ordinary skill to include a charge generation layer having an n-type and a p-type charge generation layer as described in claim 10 above. The knowledge that radialene compounds may be employed in each of a hole injection layer and a p-type charge generation layer as taught by Hummer et al. would necessarily lead one having ordinary skill in the art to consider employing the same radialene compound to serve in both the hole injection layer and p-type charge generation layer thereby satisfying claim 12. Additionally, by employing the same radialene compound in each of these layers, there is the advantage of reduced manufacturing complexity with fewer materials to be sourced, qualified, and managed within a manufacturing facility.
Claim 132 is rejected under 35 U.S.C. 103 as being unpatentable over Hummert et al. (US 2017/0373251), in view of Jankus et al., further in view of Kawamoto et al. (US 2022/0407007).
While Hummert et al. in view of Jankus et al. does not explicitly teach that each of the hole injection layer and the p-type charge generation layer comprises a radialene type p-dopant and an aromatic amine host material, one having ordinary skill in the art would have found it obvious to have prepared a light-emitting device which does satisfy this requirement as recited in claim 133 given the teachings of Kawamoto et al. and the knowledge of one having ordinary skill in the art. Specifically, Kawamoto et al. is drawn to organic electroluminescent devices which includes embodiments which comprises a p-doped hole injection layer, and wherein a plurality of light-emitting units are included where each light-emitting unit is separated by a charge generation layer, wherein the charge generation layer comprises an n-type and a p-type charge generation layer. Kawamoto et al. teaches that the matrix or host in each of the hole injection layer and p-type charge generation layer can be amine-based compounds (paragraphs 0107 and 0147). One having ordinary skill in the art understands that amine-based compounds are favorable to serve in this role as they act as effective electron donors to create charge-transfer complexes which facilitates both charge generation and injection. Additionally, by employing the same amine-based compound in each of these layers, there is the advantage of reduced manufacturing complexity with fewer materials to be sourced, qualified, and managed within a manufacturing facility. For these reasons, preparing a device which comprises a hole injection and p-type charge generation layer comprising the same matrix compound would have been obvious.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-6 and 8-14 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 25 of copending Application No. 18/531,383 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other. At least compound (G5) as recited in claim 25 of the reference application reads on formula (I) of claim 1 as variable A1 and A3 includes a group satisfying formula (II) where R1 and R5 are present and equal to CF3 and variable A2 includes a group satisfying formula (III) where Ar is substituted by two CN groups. Compound (G5) also reads on formula (IV) of claim 2 and has a total of four CN groups, satisfying claim 3. Compound (G5) also has both R1 and R5 groups equal to CF3 and all R‘ groups are CN which satisfies claim 5, and the cyano groups are adjacent which satisfies claim 6. Regarding claims 8-14, claim 25 depends on claim 1 of the reference application which claims an electroluminescent device which includes all of the device limitations of claims 8-14, namely, an anode, two emission layers, a hole injection layer, an electron injection layer, a first electron transport layer, and a charge generation layer. Claim 25 of the reference application claims that the first organic p-dopant or the second p-dopant are selected from a compound which includes compound (G5). The hole injection layer of claim 1 comprises a first organic p-dopant and the p-type charge generation layer of claim 1 comprises a second organic p-dopant.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT S LOEWE whose telephone number is (571)270-3298. The examiner can normally be reached on Monday-Friday from 8 AM to 5 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski, can be reached at telephone number 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Robert S Loewe/Primary Examiner, Art Unit 1766
1 Claim 1 cannot have both “halogen” and “Cl, F” present in the same Markush group for reasons described in the 112(b) rejection described herein.
2 Should Applicants amend claim 11 to be dependent on claim 10.
3 Claim 13 recites a generic covalent matrix compound, and the amine-based compounds taught by Kawamoto et al. satisfy this limitation.