DETAILED ACTION
Notice of Pre-AIA or AIA Status
1. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Rejections - 35 USC § 112
2. 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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
3. Claims 20, 27, and 29 rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
4. Claim 20 recites “A2 and A3 are independently selected from formula (III)…” and includes the recitation that “wherein the asterix “*” denotes the binding position…”. Given that there is no asterix included within formula (III), it is unclear where the binding position is. [based on a previous presentation of the claim] For the purposes of examination, the binding position will be interpreted as the methylene unit disposed between Ar and R’ in formula (III).
5. Claim 27 recites “The compound of claim 20, wherein two of X1 and X5 are N and two of R1 to R5 are independently selected from CN, or partially fluorinated or
perfluorinated C1 to C8 alkyl.” Given that each position of Xn can only be selected as either a nitrogen atom or a substituted carbon atom, it is unclear how X1 and X5 are both required to be N while simultaneously selecting two of R1 to R5 as substituted CRn. For the purposes of examination, the limitation will be interpreted as “wherein two of X1 to X5 are N and two of R1 to R5 are independently selected from CN, or partially fluorinated or perfluorinated C1 to C8 alkyl.”
6. Claim 29 recites the limitation “The organic electronic device of claim 28, wherein the organic semiconductor layer comprises a composition comprising a compound of formula (IV) and at least one compound of formula (IVa) to (IVd)…”. There is insufficient antecedent basis for this limitation in the claim. Given that claim 29 is dependent upon claim 28, and that claim 28 is dependent upon claim 20, it is unclear how substituents B1-B6 of formulae (IVa) to (IVd) are defined. For the purposes of examination, B1-B6 will be interpreted in accordance with the definitions provided for formula (IV) in Claim 21.
Claim Rejections - 35 USC § 103
7. In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
8. 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.
9. 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.
10. 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.
11. Claims 20-26, 28, 30, 32-33 are rejected under 35 U.S.C. 103 as being unpatentable over Ha et al. (WO 2019168368 A1, English translation obtained from WIPO).
12. Regarding claims 20-24, Ha teaches radialene compounds represented by Chemical Formula 3 (¶ [0022]-[0026], see formula below) wherein:
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X1, X2, and X3 can be CR22, CR24, and CR26 (respectively) or a nitrogen atom; and
R21-R26 can be the same or different from each other; and
R21-R26 can be selected from cyano groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups.
13. Ha teaches that radialene compounds of Chemical Formula 3 are useful as dopants within the hole injection layer by enabling more facile hole injection to adjacent layers when compared to undoped hole injection host materials, resulting in a lowered driving voltage required for the organic light emitting device (¶ [0255]).
14. Ha does not teach an exemplified compound that meets all of the limitations of
Formula (II) as per claim 20, however Ha does disclose the following radialene compound (¶ [0236], see below).
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15. The radialene compound of Ha (shown above) meets all of the limitations of claim 20, except for the C3-symmetric disposition wherein A1-A3 are all identical.
16. However, Ha teaches that the following moieties of Chemical Formula 3 (¶ [0172], see below)
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may each be independently selected as the following moiety (¶ [0173], see below) wherein:
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a34 can be an integer of 1-5 (¶ [0176]); and
when a34 is an integer of 2 or more, R34 may be the same or different from each other (¶ [0179]); and
R34 can be selected from a fluorine atom, a cyano group, a trifluoromethoxy group, or a trifluoromethyl group (¶ [0190]).
17. Given the general formula and teachings of Ha, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of the radialene compound of Ha (see line 14) wherein the trifluoromethyl and cyano substituents of one of the arenes are transposed (see circled arene). This positional isomer is shown below.
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18. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by the positional isomers of the compound represented by Ha in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as dopants in the hole injection layer of the organic light emitting device of Ha and possess the properties taught by Ha (more facile hole injection and lowered driving voltage, (¶ [0255])).
19. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP 2144.09 II.
20. Regarding claim 20, Compound Ha (isomeric) reads on formulae (I), (II), and (III) wherein:
X1 to X5 of A1 are CR1 to CR5; and
R1 is a cyano substituent; and
R3 is a perfluorinated C1 alkyl substituent; and
at least one of R1 to R5 is H; and
Ar of A2 and A3 are trifluoromethyl- and cyano-substituted C6 aryl substituents; and
R’ of A2 and A3 are cyano substituents; and
A1 and A3 are not identical.
21. Regarding claim 21, Compound Ha (isomeric) reads on formulae (IV) to (V) wherein:
X1 to X5 of B1 are the same as defined above; and
B3 and B5 are Ar as defined above; and
B2, B4, and B6 are R’ as defined above.
22. Regarding claim 22, Compound Ha (isomeric) reads on the limitation wherein X3 is CR3 and R3 is a perfluorinated C1 alkyl substituent.
23. Regarding claim 23, Compound Ha (isomeric) reads on the limitation wherein X1 is C-CN.
24. Regarding claim 24, Compound Ha (isomeric) reads on the limitation wherein X1 is C-CN.
25. Regarding claims 25 and 26, Ha exemplifies the radialene compound of Ha (see line 14) that meets all of the limitations of claim 20, except for the C3-symmetric disposition wherein A1-A3 are all identical.
26. However, given the teachings of Ha regarding Chemical Formula 3 (see ¶ [0172-0173], ¶ [0176], ¶ [0179], ¶ [0190]), it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the hydrogen atom of position R1 on one of the arenes of the radialene compound of Ha with a cyano substituent (see circled arene), because Ha teaches this variable may be preferably selected as cyano. This substitution is depicted below with Compound Ha (Modified).
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27. The substitution would have been one preferred element for another and one of
ordinary skill in the pertinent art would reasonably expect the predictable result that the
modified compound would be useful as a dopant material in the hole injection layer of the organic light emitting device of Ha and possess the properties taught by Ha (more facile hole injection and lowered driving voltage, (¶ [0255])). See MPEP 2143.I.(B).
28. Regarding claim 25, Compound Ha (Modified) reads on the limitation wherein X1 and X3 are C-CN.
29. Regarding claim 26, Compound Ha (Modified) reads on the limitation wherein at least three of R1 to R5 are independently selected from CN, partially fluorinated or perfluorinated C1 to C8 alkyl, Cl, or F. Specifically wherein:
R1 and R3 are cyano substituents; and
R5 is a perfluorinated C1 alkyl substituent.
30. Regarding claims 28, 30, 32-33, Ha teaches an organic electronic device (see Example 18 (¶ [0480]-[0483]) for device fabrication; see also Examples 18-47 in Table 2 (¶ [0494]) and Examples 48-55 in Table 3 (¶ [0508]) for devices with hole injection layers doped with radialene compounds) comprising:
an anode layer (ITO, ¶ [0481]); and
a cathode layer (Al, ¶ [0483]); and
at least one organic semiconductor layer (hole injection layer, ¶ [0482]) arranged between the anode and cathode layers; and
the at least one organic semiconductor layer comprises a radialene compound of Chemical Formula 3 (HI-2 (¶ [0466]); see Table 2 ¶ [0494], and HI-3, HI-4 (¶ [0501]); see Table 3 ¶ [0508]).
at least one photoactive layer arranged between the anode and cathode layers (BH1 and BD1 as host and dopant respectively (¶ [0466] and ¶ [0482]), and the at least one organic semiconductor layer (hole injection layer, ¶ [0482]) is arranged between the anode layer and the at least one photoactive layer (¶ [0482]).
31. While Ha does not teach Compound Ha (isomeric) (see regarding claims 20-24) in an organic electronic device, Ha does generally teach uses of radialene compounds represented by Chemical Formula 3 in organic electronic devices of claim 28.
32. At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the organic electronic devices of Ha by using the Compound Ha (isomeric) as the dopant of the hole injection layer, based on the teaching of Ha. The modification would have been a combination of prior art elements according to known methods to yield predictable results and one of ordinary skill in the art would reasonably expect the modified organic electronic devices to possess the benefits taught by Ha (more facile hole injection and lowered driving voltage, (¶ [0255])). See MPEP 2143(I)(A).
33. The modified organic electronic device of Ha comprising the compound Ha
(isomeric) in the hole injection layer reads on all the limitations of claims 28 and 30.
34. Regarding claims 32-33, the modified organic electronic device of Ha comprising the compound Ha (isomeric) in the hole injection layer reads on claim 32 wherein the organic electronic device is an electroluminescent device and on claim 33 wherein the organic electronic device is an organic light emitting diode (¶ [0005]).
35. Claims 27 and 29 are rejected under 35 U.S.C. 103 as being unpatentable over Ha et al. (WO 2019168368 A1, English translation obtained from WIPO) as applied to claim 20 above, and further in view of Hummert et al. (US 20170373251 A1).
36. Regarding claim 27, Ha, as modified above, teaches all of the features with respect to claim 20 as outlined above.
37. Ha, as modified above, does not exemplify a structure wherein two of X1 to X5 are nitrogen atoms as required per claim 27.
38. Hummert teaches radialene compounds represented by formula 1 (¶ [0019], see formula below) wherein:
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A1 and A2 are independently aryl- or heteroaryl-substituted cyanomethylidene groups (¶ [0019]); and
A1 and A2 can be the same or different from each other (¶ [0030]).
39. Hummert exemplifies compound B1 (shown below, ¶ [0041]) wherein pyrimidine is shown to be a preferred heterocyclic substituent for the cyanomethylidine moieties of the [3]-radialene compounds.
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40. Hummert also teaches that [3]-radialene compounds of Formula (I) are useful as p-dopants in organic light emitting diodes (¶ [0024]) and that substitutions of the aryl- and heteroaryl groups within the cyanomethylidene moieties of A1 and A2 result in predictable changes of the dopant’s redox couple as measured by cyclic voltammetry (¶ [0033]-[0035]). Additionally, Hummert teaches that the capacity to alter the dopant’s redox potential can be leveraged to lower the required doping concentration and provide increased flexibility during electronic device design process (¶ [0039]).
41. At the time the invention was effectively filed, it would have been obvious to one
of ordinary skill in the art to have modified the radialene compound of Ha (see line 14) by substituting one of the aryl groups of the aryl cyanomethylidene moieties
for a pyrimidine heteroaryl group, based on the teachings of Hummert with the
motivation to provide a p-dopant material with a predictably alterable redox couple (¶ [0033]-[0035]) and possess the benefits taught by Hummert (lowered doping concentration and increased flexibility during electronic device design process (¶ [0039])).This substitution provides the following modified compound (see below).
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42. The Compound of Ha (Hummert Modification) reads on all of the limitations of claims 20 and 27.
43. Regarding claim 29, Ha, as modified above, teaches all of the features with respect to claims 20 and 28 as outlined above.
44. Ha, as modified above, does not teach an organic semiconductor layer comprising a compound of formula (IV) and at least one compound of formula (IVa) to (IVd) as required per claim 29.
45. Hummert teaches a synthetic process for preparing C3-symmetric and asymmetric [3]-radialene compounds (Abstract), and further discloses that the inventive radialene compounds produced by this synthetic process may comprise all possible geometric isomers with respect to the disposition of the substituents across the exocyclic double bonds (¶ [0033]).
46. Hummert discloses that the final step in the synthetic process for preparing the [3]-radialene compounds is an oxidation reaction (¶ [0022]) and teaches the following example involving Compound B5 (¶ [0094], shown below).
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47. Given that the cyano and (hetero)aryl substituents on the radialene precursor are connected to single bonds (see circled areas above) capable of free rotation prior to the oxidation reaction, and given the teaching of Hummert regarding the presence of geometric isomers of the synthesized radialene compounds (¶ [0033]), it would be obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to reasonably expect the generation of regioisomeric [3]-radialene compounds produced by the final oxidation reaction as described above, absent any indication of unexpected results.
48. One possible regiosiomer of the Compound Ha (Hummert Modification) is shown below, which reads on formula (IVa) as per claim 29.
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49. One of ordinary skill in the art would have been motivated to produce organic electronic devices comprising a composition of Compounds Ha (Hummert Modification) and Ha (Hummert isomeric) in the organic semiconductor layer having the benefits taught by Hummert (predictably alterable redox couple (¶ [0033]-[0035]) and increased flexibility during electronic device design (¶ [0039])) in order to pursue the known options within his or her technical grasp with a reasonable expectation of success,
absent any indication of unexpected results. See MPEP 2143.I.(E).
50. Claims 31 and 34 are rejected under 35 U.S.C. 103 as being unpatentable over Ha et al. (WO 2019168368 A1, English translation obtained from WIPO) as applied to claim 20 above, and further in view of Ma et al. (US 20180166509 A1).
51. Regarding claims 31 and 34, Ha, as modified above, teaches all of the features with respect to claims 20 and 28 as outlined above.
52. Ha does not teach an organic electronic device that comprises at least two photoactive layers wherein at least one of the at least one organic semiconductor layers is arranged between the first and the second photoactive layer.
53. Ma teaches an organic electronic device comprising:
an anode layer (¶ [0007]); and
a cathode layer (¶ [0007]); and
at least two emitting layers arranged between the anode and cathode layers (¶ [0007]); and
a charge generation layer between the adjacent emitting layers wherein the charge generation layer includes a P-type semiconductor dopant (¶ [0007]).
54. The specific P-type semiconductor dopant is represented by the following formula (see below, ¶ [0007]) wherein:
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n is an integer greater than or equal to 1 (¶ [0008]); and
X1-X3 each has an independent structure of
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(¶ [0008]); and
R’ is selected from any substituted aryl or heteroaryl group wherein the substituent(s) include at least one electron acceptor group (¶ [0008]).
55. Ma also teaches that organic light emitting diodes possessing charge generation layers disposed between two adjacent light emitting layers have improved luminous efficiency and lowered driving voltages when the charge generation layers include radialene-derived P-type semiconductor dopants (¶ [0035]).
56. At the time the invention was effectively filed, it would have been obvious to one
of ordinary skill in the art to have modified the modified organic electronic device of Ha (see regarding claim 28) by including a charge generation layer doped with Compound Ha (isomeric) between a first light emitting layer and a second light emitting layer, based on the teachings of Ma with the motivation to provide an organic electronic device with
improved luminous efficiency and lowered driving voltages (¶ [0035]). The resulting device of Ha (Ma Modification) reads on all of the limitations of claim 31.
57. Ma also teaches a display device comprising all of the aforementioned limitations of claims 28 and 31 (¶ [0011]).
58. At the time the invention was effectively filed, it would have been obvious to one
of ordinary skill in the art to have modified the modified organic electronic device of Ha (Ma Modification) by incorporating it into a display device, based on the teachings of Ma with the motivation to provide a display device with improved luminous efficiency and lowered driving voltages (¶ [0035]). The resulting display device of Ha (Ma Modification) reads on all of the limitations of claim 34.
Double Patenting
59. 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).
60. 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).
61. 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.
62. 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.
63. Claims 20-22 and 26 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 14 of copending Application No. 18/722,072 (reference application, hereafter Application ‘072).
64. Although the claims at issue are not identical, they are not patentably distinct from each other because claim 14 of Application ‘072 recites a compound defined by formulae (XI), (XIIa), and (XIII), and further provides structural limitations that are commensurate with the scope of claims 20-22 and 26 of the instant application. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
65. Regarding claims 20-22 and 26 of the instant application, Application ‘072 discloses the following formulae (XI), (XIIa), and (XIII) in claim 14 wherein:
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A1 in Formula (XI) is represented by Formula (XIIa); and
X1-X3, X5 are selected from CR1-CR3, CR5 or N; and
X4 is selected from CR4; and
A2 and A3 in in Formula (XI) is represented by Formula (XIII).
66. Application ‘072 also discloses Compound B20 (see below), which meets all of the further structural limitations of claim 14 of Application ‘072.
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67. Regarding claim 20 of the instant application, Compound B20 of Application ‘072 reads on formulae (I) to (III) wherein:
X1 to X5 are CR1 to CR5; and
R1 and R5 are perfluorinated C1 alkyl substituents; and
R2 and R4 are cyano substituents; and
R3 is a hydrogen atom; and
Ar of A2 and A3 are fluoro- and cyano-substituted C6 aryl substituents; and
R’ of A2 and A3 are cyano substituents; and
A1 and A3 are not identical.
68. Regarding claim 21 of the instant application, Compound B20 of Application ‘072 reads on formulae (IV) to (V) wherein:
X1 to X5 of B1 are the same as defined above; and
B3 and B5 are Ar as defined above; and
B2, B4, and B6 are R’ as defined above.
69. Regarding claim 22 of the instant application, Compound B20 of Application ‘072 reads on the limitation wherein X3 is CR3 and R3 is a hydrogen atom.
70. Regarding claim 26 of the instant application, Compound B20 of Application ‘072 reads on the limitation wherein at least three R1 to R5 are independently selected from CN, partially fluorinated or perfluorinated C1 to C8 alkyl, Cl, or F. Specifically, wherein R1 and R5 are perfluorinated C1 alkyl substituents and R2 and R4 are cyano substituents.
71. Although the claims of the instant application and Application ‘072 are not
identical, one of ordinary skill in the art at the time of filing would recognize that the
claims of the instant application and Application ‘072 are obvious variants of each other
as they overlap in scope.
Conclusion
72. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Brandon J. Cooper whose telephone number is (571)272-0005. The examiner can normally be reached Monday - Friday 8:30 AM - 5:00 PM.
73. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
74. 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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/B.J.C./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786