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. For utmost clarity, claim 1 should be amended to include the limitation “wherein the asterisk “*” denotes the binding position” for utmost clarity. This limitation is included verbatim in Applicants specification.
Claim 1 is further objected to. It appears that there is a period after “D or H”, which should be amended to be a comma.
Claim 1 is further objected to. The limitation “selected from CN, partially or perfluorinated C1 to C6 alkyl, halogen, Cl, F, D” as found on the 3rd and 4th to last lines of claim 1 should be amended to either “selected from the group consisting of CN, partially fluorinated or perfluorinated C1 to C6 alkyl, halogen, and D” or alternatively to “selected from the group consisting of CN, partially fluorinated or perfluorinated C1 to C6 alkyl, Cl, F, and D”.1
Claims 7 and 8 are objected to. All five structures recited in claim 7 and all five structures recited in claim 8 should include “*” at the appropriate atom for utmost 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 1-9 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). In the present instance, claim 1 recites the broad recitation halogen, and the claim also recites “Cl, F” (the first instance) or “Cl or F” (two additional instances in claim 1) which are the narrower statements of the limitation. 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” where necessary. Claims 2-4 and 6-8 are included in this rejection as they depend from rejected claim 1. Additionally, each of claims 5 and 9 are rejected for the same reason as claim 1 as they both recite the limitation “halogen, Cl or F”. Claims 5 and 9 should be amended in the same manner as suggested for claim 1 above to overcome this rejection.
Claims 10-15 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. Claim 10, which is written as an independent claim, recites the limitation that the organic semiconductor layer comprises a compound of formula (I). However, formula (I) is not defined anywhere in claim 10, rendering the claim indefinite. For purposes of further examination, claim 10 will be interpreted as being dependent on claim 1. Claims 11-15 are included in this rejection as they are dependent on claim 10. Applicants may overcome this rejection by amending claim 10 to be dependent from claim 1, which does recited formula (I). For purposes of further examination, claim 10 is interpreted as being dependent on claim 1, and is also interpreted as being an independent claim where the features of formula (I) from claim 1 are included.
Claim 11 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 11 recites “a compound of formula (IV)” in line 2, which does not have proper antecedent basis. While it could be interpreted that claim 11 may be dependent on claim 2 which does recite formula (IV), claim 11 is dependent on claim 10, which is dependent on claim 1, which comprises a compound of formula (I). As such, there is no easy or proper way to interpret the claim dependency of claim 11.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 11 is rejected under 35 U.S.C. 112(d) as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Clam 11, which is dependent on claim 10, recites the limitation “a compound of formula (IV)” which is not recited in claim 10. Claim 11 therefore fails to further limit claim 10. Applicant may cancel the claim, amend the claim to place the claim in proper dependent form, rewrite the claim in independent form, or present a sufficient showing that the dependent claim complies with the statutory requirements.
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.
Claims 1-8, 10, 12, 14, and 15 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Pan et al. (US 2023/0389414). Pan et al. has a foreign priority date of 6/10/21 which is before Applicants filing date but after Applicants foreign priority claims and therefore qualifies as prior art under 102(a)(2). Applicants can overcome this rejection by perfecting their foreign priority claims. Applicants have nine foreign priority documents and providing a certified English language translation of any one or more of these documents which show support for the claimed subject matter would overcome this rejection.
Claim 1: Pan et al. teaches compounds which adhere to formula (I) of claim 1. Specific compounds are taught in paragraph 0056. Several of the compounds taught in paragraph 0056 anticipate all of the structural limitations of claim 1. One such compound is
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(page 11). As applied to formula (I), this compound has A1 equal to a group which anticipates formula (II) with R’ equal to CN, X1, X2, X4, and X5 equal to CR1, CR2, CR4, and CR5, respectively with R1 and R5 equal to F and R2 and R4 equal to CN, Variable X3 is equal to CR3, where R3 is equal to D. This compound satisfies the first proviso regarding formula (II) in that at least one of the R1, R2, R4, and R5 groups is selected from CN. In the compound above, variables A2 and A3 anticipate formula (III) with R’ equal to CN and Ar equal to a substituted C6 aryl group where the substituents are selected from CN, F, and D.
Claim 2: The above compound also anticipates formula (IV) of claim 2 with all variable assignments being described in claim 1.
Claim 3: The compound above also anticipates claim 3 in that two of R1, R2, R4, and R5 are selected from CN.
Claim 4: The compound above also anticipates claim 4 in that both of R2 and R4 are selected from CN.
Claim 5: The compound above also anticipates claim 5 in that one of R1, R2, R4, and R5 is selected from CN, and at least one of R1, R2, F4, and R5 is selected from F.
Claim 6: For claim 6, the compound
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taught on page 10 of Pan et al. is relied upon. This compound anticipates all of the structural limitations of formula (1) of claim 1 with A1 being a group which anticipates formula (II). Variables A2 and A3 anticipate formula (III) of claim 1. Additionally, this compound anticipates the limitation of claim 6 that at least one of R1, R2, R4, and R5 is selected from a perfluorinated methyl group and at least one of X1, X2, X4, or X5 is N.
Claims 7 and 8: The compound above does not include any of the moieties recited in claims 7 and 8, thereby anticipating claims 7 and 8.
Claims 10, 12, 14, and 15: The compounds taught by Pan et al. are employed as p-dopants in organic electroluminescent devices. OLED2 as shown in Table 2 of Pan et al. is drawn to an organic light emitting device where compound 3 which has the structure
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(page 36), is employed as a p-dopant. Device example OLED2 comprises an anode, a hole transport region comprising said p-dopant and an amine matrix material/amine host material, a light emitting layer comprising a host material and a dopant, an electron transport region, and a cathode (paragraph 0177). Therefore OLED2 anticipates all of the structural and device limitations of claims 10, 12, and 14. Additionally, OLED2 is by its very nature a display device, thereby anticipating claim 15.
Claims 1, 2, 4, and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hollis et al. (J. Coord. Chem. 2014, 67(8), 1367-1379).
Claims 1, 2, and 4: Hollis et al. teaches compound 3 which has the structure
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(page 4). This compound anticipates formula (1) where A1 anticipates formula 2 with all X groups equal to C, R1, R2, R3, and R5 equal to H and R4 equal to CN. Variable R’ is equal to Ar which is a cyano-substituted C6 aryl group. A2 and A3 anticipate formula (III) with Ar and R’ both equal to a cyano-substituted C6 aryl group. Compound 3 above also anticipates formula (IV) of claim 2 with B1 satisfying formula (V) with all X equal to C and R1, R2, R3, and R5 equal to H and R4 equal to cyano, (which also anticipates claim 4) B3 and B5 are Ar where Ar is a substituted C6 aryl group substituted with CN, and B2, B4, and B6 are equal to R’ which is equal to Ar.
Claim 11: Because variable R’, variable Ar, and variable B1 in formula (II) are all identical in compound 3 above, and because claim 22 allows for Ar, R’ and B1 to all be the same, all of formulae (IV) and (IVa) to (IVd) read on compound 3. During the synthesis and/or characterization of compound 3 above, there would inherently be a composition comprising at least a crude reaction mixture comprising compound 3 or a purified product comprising compound 3 in a solvent (such as a solvent for proton NMR characterization). Compound 3 above can be said to be a mixture of all 5 compounds recited in claim 11. The claims do not require R’, Ar, and B1 to be different. If this were the case, then compound 3 could not be relied upon to reject claim 11.
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, 2, 4, 7, 8, 10, 12, 14, and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Ma et al. (US 2017/0346032).
Claim 1: Ma et al. teaches organic light emitting diodes which comprises an anode, a cathode, and a plurality of organic layers stacked therebetween, which includes an auxiliary light-emitting layer comprising a host material and a p-dopant (claim 1 of Ma et al.). The p-dopant is taught and claimed as being a [3]-radialene compound of chemical formula (I). In chemical formula (I) each or X1-X3 has a chemical structure of =C(R’)(CN) where each R’ is a substituted aryl or heteroaryl group where the substituent(s) is an electron acceptor group. In paragraph 0045, Ma et al. teaches that the substituted aryl groups which may be employed includes
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. A person having ordinary skill in the art would have found the preparation of any one of the three positional isomers for the aryl group
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, including ortho- and meta-positional isomers, to be prima facie obvious. The preparation of ortho- or meta-isomers results in each of X1-X3 of Ma et al. to be respectively equal to the structures
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. The motivation to prepare such compounds stems from the teachings of Ma et al. The resulting compounds comprising X1-X3 above as applied to chemical formula 1 of Ma et al. would result in the structures
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. These two compounds satisfy all of the structural limitations of formula (I) of claim 1 with A1 equal to a group which satisfies formula (II) with R’ equal to CN, all X1-X5 groups equal to carbon and R3-R5 equal to hydrogen, and one of R1 and R2 equal to cyano, depending on the structure above. This satisfies the first proviso regarding A1. Variables A2 and A3 in the compounds above satisfy formula (III) with R’ equal to CN and Ar equal to a substituted C6 aryl group having one CN.
Claim 2: The compounds above also satisfy formula (IV) of claim 2 with all variable assignments being described in claim 1 above.
Claim 4: The compound on the right shown directly above satisfies claim 4 as one R2 is equal to CN.
Claims 7 and 8: The two compounds shown directly above do not include any of the groups shown in claims 7 or 8, thereby satisfying claims 7 and 8.
Claims 10, 12, 14, and 15: Ma et al. teaches employing the compounds taught and suggested therein in the manner recited in claim 1 therein. Claim 1 of Ma et al. satisfies all of the device limitations of claims 10, 12, and 14. Additionally, the organic light-emitting diodes claimed by Ma et al. are by their very nature display devices, thereby satisfying claim 15.
Claims 10 and 13-153 are rejected under 35 U.S.C. 103 as being unpatentable over Hatwar et al. (US 2010/0288362) in view of Kita et al. (JP-3960131). Copies of the original and a machine translation of Kita et al. are included with this Office action.
Claim 10: Hatwar et al. teaches tandem organic light-emitting devices whose architecture is shown in Fig. 3 . The tandem OLED is comprised of a substrate, an anode, a first electroluminescent unit, an intermediate connecting region, a second electroluminescent region, and a cathode (paragraph 0100 and Fig. 3). The connecting region comprises a p-type layer (308) (paragraph 0100 and Fig. 3). Hatwar et al. teaches that suitable materials which may serve as the p-type dopant in the intermediate connecting region includes those taught by JP-3960131 (Kita et al., paragraph 0072). This teaching renders obvious to a person having ordinary skill in the art to employ any one of the explicitly taught compounds of Kita et al, including compound (9) which has the structure
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(page 8). As applied to Formula (I), variable A1 satisfies formula (II) with R’ equal to Ar, where Ar is a CF3-substituted phenyl group, all X groups equal to C and R1, R2, R3, and R5 equal to H, and R4 equal to -CF3 which satisfies the proviso regarding A1. Variables A2 and A3 satisfy formula (III) of claim 1 with R’ and Ar both equal to a CF3-substitued phenyl group. Because Hatwar et al. explicitly teaches that the compounds taught by Kita et al. may be employed to serve as the p-type material in the devices taught therein, it would have been prima facie obvious to one having ordinary skill in the art to have employed any one of the compounds taught by Kita et al., including compound (9), as such a combination is readily obvious and one of ordinary skill in the art would have reasonably expected that compound (9) would serve as an effective p-dopant. The motivation to select such a p-dopant is rooted within the teachings of Hatwar et al. Fig. 3 explicitly teaches all of the device limitations of claims 10 and 12-14 as taught above. Additionally, the tandem OLED a display device which also satisfies claim 15.
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 claims at issue 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); and 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 a nonstatutory double patenting ground provided the reference application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form 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 http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1, 3, 4, 6, 10, and 12-15 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 9 of copending Application No. 18/262,837 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other. Claim 9 of the reference application is drawn to compounds where each of Ar1 through Ar3 are selected from the groups recited therein. Several of the groups recited in claim 9, when applied as variables Ar1 through Ar3 of instant claim 1, result in radialene compounds which satisfy the limitations of formula (I) with Ar1 corresponding to A1 and additionally satisfying formula (II). The Ar1 through Ar3 groups recited in claim 9 of the reference application include the same five compounds recited in instant claims 7 and 8. Claims 7 and 8 are not included in this rejection as claims 7 and 8 are written to exclude such compounds. When Ar1 through Ar3 are selected form these five compounds all of the structural limitations regarding A1 through A3 of instant claims 1, 3, 4, and 6 are satisfied. Additionally, R’ as recited in claim 1 of the reference application is substantially similar in scope to R’ of the instant application so as to warrant a prima facie case of obviousness. Specifically, it would have been obvious to one having ordinary skill in the art to select groups as R’ as claimed by the reference application which are the same as the R’ groups as claimed in the instant application due to the significant overlap in claim scope. The device limitations recited in claim 1 of the reference application (claim 9 of the reference application is directly dependent on claim 1) read on all of the device limitations recited in claims 10 and 12-15.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1, 3, 4, 6, 10, and 12-15 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 6 of copending Application No. 18/262,873 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other. Claim 6 of the reference application is drawn to compounds where each of Ar1 through Ar3 are selected from the groups recited therein. Several of the groups recited in claim 9 when applied as variables Ar1 through Ar3 of instant claim 1, results in radialene compounds which satisfy the limitations of formula (I) with Ar1 corresponding to A1 and satisfying formula (II). The Ar1 through Ar3 groups recited in claim 7 include the same five compounds recited in claims 7 and 8. Claims 7 and 8 are not included in this rejection as claims 7 and 8 are written to exclude such compounds. When Ar1 through Ar3 are selected form these five compounds all of the structural limitations regarding A1 through A3 are satisfied. Additionally, R’ as recited in claim 5 of the reference application is CN, with claim 6 being dependent on claim 5 in the reference application. The device limitations recited in claim 1 of the reference application (with claim 6 being dependent on claims 1 and 5) read on all of the device limitations recited in claims 10 and 12-15.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Comment on Patentability
While all claims stand rejected, the prior art does not teach or reasonably suggest compounds of formula (I) where A1 is a group of formula (II) where X3 is CH or CD and where one of R1, R2, R4, and R5 is a substituent selected from CN and partially fluorinated or perfluorinated C1-C8 alkyl, and the remaining three of R1, R2, R4, and R5 is selected from halogen.
Relevant Art Cited
Additional prior art documents which are relevant to Applicants invention can be found on the attached PTO-892 form.
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 above.
2 For rejection purposes, claim 11 is being interpreted as being dependent on claim 2. But as stated in the 112 rejection of claim 11 above, there is no easy way to fix all of the issues regarding claim 11 since is it dependent on claim 10. This rejection is presented should Applicants overcome all of the 112 issues with claims 10 and 11.
3 With the understanding that claim 10 would be amended to be an independent claim which includes the limitations of claim 1.