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 .
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 1-2, 4, and 8-10 are rejected under 35 U.S.C. 102(a)(1) and 35 U.S.C. 102(a)(2) as being anticipated by Yen et al. (US2021/0061787A1, hereinafter "Yen").
In the pertinent art of organic light-emitting devices, Yen discloses an organic compound such as compound C218, shown below, and an organic light-emitting device comprising the organic compound as a host or a hole blocking layer.
PNG
media_image1.png
1412
1650
media_image1.png
Greyscale
Compound C218 of Yen is a compound of instant Formula 1 in claim 1 wherein Ip contains a 7H-indeno[1,2-a]pyrene skeleton, Ar is an unsubstituted, nitrogen atom-containing heteroaryl group, FL is a skeleton having a structure represented by formula 2, X is a sulfur atom, and L1 and L2 are direct bonds (pg 173, claim 7).
Regarding instant claims 8-9, the Compound C218 of Yen has an indenopyrene skeleton containing an alkyl group having 1 carbon or “methyl” group.
Regarding instant claim 10, the Compound C218 of Yen is a compound of instant claim 1 wherein FL is dibenzothiophene and contains an aryl group having 6 carbon atoms. Note that the word “contains” is interpreted to not exclude additional functionality: Compound C218 “contains” an aryl group having 6 carbon atoms that happens to be substituted with a phenyl group. Therefore, the compound C218 of Yen anticipates instant claims 1-2, 4, and 8-10.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 3, 11, and 14-18 are rejected under 35 U.S.C. 103 as being unpatentable over Yen et al. (US2021/0061787A1, hereinafter "Yen") as applied to claims 1-2, 4, and 8-10 as described above.
Yen teaches the Compound C218, as applied to claims 1-2, 4, and 8-10, as described above. Yen teaches the Compound C218 is a compound of general formula 1 where substituent Z on the carbazole group is represented by formula 3, both shown below, wherein Y is a sulfur atom and R16 is an aryl group (¶ [0037] – [0038]).
PNG
media_image2.png
994
3756
media_image2.png
Greyscale
Yen does not particularly limit the identity of Y to a sulfur atom, defining the group as selected from CR7R8, and taught a specific compound C232 wherein Y is a carbon atom and R7R8 are methyl groups, also known as “dimethyl fluorene,” shown below (¶ [0038], claim 7 pg 176).
PNG
media_image3.png
1680
1700
media_image3.png
Greyscale
Yen teaches that, when used in an organic light-emitting device, a compound of Formula 1 of Yen exhibits performance better than a prior art OLED material with a low driving voltage, high current efficiency, and long half-life (¶ [0062] – [0066], Table 1).
Therefore, 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 compound C218 of Yen in the light-emitting device of Yen, with Y as carbon or a “dimethylfluorene” group, based on the teachings of Yen. The motivation for doing so would have been to obtain a device with low driving voltage, high current efficiency, and long half-life (¶ [0062] – [0066], Table 1).
The resulting Modified Compound of Yen is shown below and reads on (1) instant claim 3 wherein FL contains a fluorene skeleton and (2) instant claim 11 wherein FL contains a methyl group.
PNG
media_image4.png
200
400
media_image4.png
Greyscale
Modified Compound of Yen
Yen teaches an organic light-emitting device example 400, containing a first electrode and a second electrode, and between the pair of electrodes comprising a light emitting layer, wherein the light emitting layer contains a dopant D1 and a host material of the Formula 1 of Yen (Fig. 2, Table 1, [0051] – [0081]). Yen teaches the above but does not teach a specific device with the compound C218, described above, of Yen.
Yen teaches an anode, a cathode, and an organic light-emitting layer and the compound is in the organic light-emitting layer with a dopant compound as discussed above. It would have been obvious to use the compound C218 in the organic layer with the device structure of first electrode, organic light-emitting layer containing C218 and dopant D1, and second electrode as Yen demonstrates this device structure was known prior to the effective filing date of the claimed invention.
The resulting organic light-emitting device reads on instant claim 14-15. Regarding claim 16, the dopant compound D1 reads on the first compound of instant claim 16. Yen teaches the claimed invention above but does not expressly teach the dopant D1 having a higher lowest excited singlet energy than compound C218. It is reasonable to presume that the LUMO of D1 is higher than the LUMO of C218 is inherent to the organic light-emitting device of Yen. Support for said presumption is found in that the host material must have a LUMO shallower than the emitter to confine electrons on the emitter, essential for high EQE as taught by noctiluca (https://noctiluca.eu/homo-lumo-oled-materials/). Therefore, the LUMO of D1 is expected to be higher than the LUMO of C218. Note that a webpage is relied upon and included with the office action.
Regarding claim 17, dopant D1 is bis(2-phenylpyridinato)(2,4-diphenylpyridinato)-iridium(III), which reads on the first compound being a hydrocarbon compound of instant claim 17 (¶ [0071]).
Regarding claim 18, Yen teaches the light emitting layer may comprise multiple compounds wherein the host compound C218 is expected to have a lower LUMO energy, as described above (¶ [0051] – [0061]).
Claims 19-24 are rejected under 35 U.S.C. 103 as being unpatentable over Yen et al. (US2021/0061787A1, hereinafter "Yen") as applied to claims 1-4, 8-11, and 14-18 as described above in further view of Miyashita et al. (US2020/0403173A1, hereinafter "Miyashita").
Yen teaches the compound C218 inside of an organic light-emitting layer of an organic light-emitting device that reads on claims 1-4, 8-11, and 14-18 as described above. However, Yen is silent on the organic light-emitting device used in a (1) display apparatus comprising multiple pixels; (2) a photoelectric conversion apparatus comprising an optical unit including multiple lenses; (3) an electronic apparatus comprising a display unit; (4) a lighting apparatus comprising a light source; (5) a moving object comprising a lighting unit; and (6) an image-forming apparatus comprising a photoconductor of instant claims 19-24 respectively.
In the relevant art of organic light-emitting devices, Miyashita teaches an organic light-emitting device and an organic compound, such as but not limited to compound EM1, inside the organic layer of a light-emitting device, featuring a polycyclic aromatic ring system featuring pyrene units attached to another polycyclic aromatic ring system such as a fluorene (¶ [0077]). The compounds of Miyashita are similar to the compounds of Yen in that both contain polycyclic aromatic ring systems containing pyrene connected to an aromatic ring system that is fluorene-like. In the case of Yen, compound C218 features a fluorene-like system wherein the carbon atom substituted by two methyls is replaced by either N or S, and in other exemplified compound is replaced by Si or C. Miyashita teaches that the organic light-emitting element that contains such a polycyclic aromatic ring system may be included in a display apparatus comprising a plurality of pixels and a transistor connected to the organic light-emitting element (pg 42 claim 16). Miyashita teaches that the organic light-emitting element may be included in an image pickup apparatus comprising an optical unit including a plurality of lenses, an image pickup element configured to receive light passing through the optical unit and a display unit configured to display an image captured by the image pickup unit (pg 42 claim 17). Miyashita teaches the organic light-emitting element may be included in an illumination apparatus comprising a light source and a light diffusion unit (pg 43 claim 18). Miyashita teaches the organic light-emitting element may be included in a moving object comprising a light fixture and a body provided with the lighting fixture (pg 43 claim 19). Miyashita teaches the organic light-emitting element may be included in an electronic device including a display unit, an operation unit, and a housing wherein the housing may include a circuit, a battery, and a communication unit (¶ [147]).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to further include the organic light-emitting device of Yen in the light-emitting devices of Miyashita, based on the teachings of Yen. The motivation for doing so would have been to obtain a device with low driving voltage, high current efficiency, and long half-life as taught by Yen (¶ [0062] – [0066], Table 1).
The Modified Device of Yen and Miyashita reads on instant claims 19-24.
Claims 1-3 and 8-13 are rejected under 35 U.S.C. 103 as being unpatentable over Sekiguchi et al. (WO2010/053210A1, hereinafter "Sekiguchi").
In the pertinent art of organic light-emitting devices, Sekiguchi teaches an organic light-emitting device that includes an indenopyrene compound of Formula 2 including a specific compound 45 that is a compound of Formula 2 wherein n is 2 and L is a methyl-substituted aromatic group “fluorene,” both shown below (pg 4, 22).
PNG
media_image5.png
1517
2224
media_image5.png
Greyscale
Sekiguchi does not particularly limit the identity of L to fluorene and defines the L group as represented by an n-valent substituted or unsubstituted fused polycyclic aromatic group, an n-valent substituted or unsubstituted heterocyclic group wherein:
the polycyclic aromatic group may be represented by bifluorene
the heterocyclic group may be represented by pyridine and the like (pg 18-19).
Sekiguchi teaches specific examples of compounds wherein L is pyridine (compound 31), quinoline (compound 32), and pyrimidine (compound 34), shown below (pg 17).
PNG
media_image6.png
932
1879
media_image6.png
Greyscale
Sekiguchi teaches that an organic light-emitting device containing the indenopyrene compound of the present invention provides for a device having an optical output with high luminance, high color purity, and high efficiency that is produced at a relatively low cost (pg 3). Sekiguchi teaches light-emitting devices Example 1-3 containing an indenopyrene compound that displays a high quantum yield wherein the luminance and light emitting efficiency can be improved (pg 44-45 Table 1).
Therefore, 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 group L in the compound 45 of Sekiguchi from a methyl-substituted fluorene group to a methyl-substituted pyrimidine group in the light-emitting device of Sekiguchi, based on the teachings of Sekiguchi. The motivation for doing so would have been to obtain a device with displays a high quantum yield, improved luminance, and improved light emitting efficiency as taught by Sekiguchi (pg 44-45 Table 1).
The resulting Modified Compound of Sekiguchi is shown below and reads on claim 1-3 and 8-12 because the Modified Compound of Sekiguchi is a compound of instant formula 1 in instant claim 1 wherein:
Ip is an indenopyrene-containing skeleton;
Ip contains a 7H-indeno[1,2-a]pyrene skeleton;
Ip contains a methyl group and a tert-butyl group;
Ar is a substituted nitrogen-containing heteroaryl group;
Ar contains an alkyl group having 1 carbon atom;
Ar contains a pyrimidine skeleton;
Fl is an indenopyrene skeleton;
Fl contains a methyl group and a tert-butyl group;
L1 and L2 are each independently a direct bond.
PNG
media_image7.png
200
400
media_image7.png
Greyscale
Modified Compound of Sekiguchi
Regarding claim 13, the Modified Compound of Sekiguchi teaches the above, however, it fails to teach the instant Ar group containing a tert-butyl group of instant claim 13. Sekiguchi does not particularly limit the substitution of the L group, defining the L group as being unsubstituted or substituted wherein the substituents may be selected from alkyl groups such as methyl and tert-butyl (pg 19).
Therefore, 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 group L in the Modified Compound of Sekiguchi from a methyl-substituted pyrimidine group to a tert-butyl-substituted pyrimidine group in the light-emitting device of Sekiguchi, based on the teachings of Sekiguchi. The motivation for doing so would have been to obtain a device with displays a high quantum yield, improved luminance, and improved light emitting efficiency as taught by Sekiguchi (pg 44-45 Table 1).
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 group L in the Modified Compound of Sekiguchi from a methyl-substituted pyrimidine group to a tert-butyl-substituted pyrimidine group in the light-emitting device of Sekiguchi, because it would have been a choice from a finite number of identified, predictable solutions of a compound useful as the indenopyrene compound in the organic layer of the organic light-emitting device of Sekiguchi and possessing the benefits taught by Sekiguchi. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 2 of Sekiguchi having the benefits high quantum yield, improved luminance, and improved light emitting efficiency as taught by Sekiguchi in order to pursue the known options within his or her technical grasp with a reasonable expectation of success (pg 44-45 Table 1). See MPEP 2143.I.(E).
The Modified Compound 2 of Sekiguchi is shown below and reads on instant claim 13.
PNG
media_image8.png
200
400
media_image8.png
Greyscale
Modified Compound 2 of Sekiguchi
Regarding claim 7, the compound 45 of Sekiguchi, as described above, fails to teach the instant Ar group as a 9,9’spirobifluorene skeleton of instant claim 7. Sekiguchi does not particularly limit the L group to fluorene, defining the L group as being represented by fluorene and bifluorene (pg 19).
Therefore, 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 group L in the compound 45 of Sekiguchi from a fluorene group to a bifluorene group in the light-emitting device of Sekiguchi, based on the teachings of Sekiguchi. The motivation for doing so would have been to obtain a device with displays a high quantum yield, improved luminance, and improved light emitting efficiency as taught by Sekiguchi (pg 44-45 Table 1).
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 group L in the compound 45 of Sekiguchi from a fluorene group to a bifluorene group in the light-emitting device of Sekiguchi, because it would have been a choice from a finite number of identified, predictable solutions of a compound useful as the indenopyrene compound in the organic layer of the organic light-emitting device of Sekiguchi and possessing the benefits taught by Sekiguchi. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 2 of Sekiguchi having the benefits high quantum yield, improved luminance, and improved light emitting efficiency as taught by Sekiguchi in order to pursue the known options within his or her technical grasp with a reasonable expectation of success (pg 44-45 Table 1). See MPEP 2143.I.(E).
The Modified Compound 3 of Sekiguchi is shown below and reads on instant claim 7.
PNG
media_image9.png
200
400
media_image9.png
Greyscale
Modified Compound 3 of Sekiguchi
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 8-11 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 and 7 of U.S. Patent No. 8,628,863 B2. Although the claims at issue are not identical, they are not patentably distinct from each other because the compounds of Formula 1 in instant claim 1 overlap in scope with compounds of Formula 2 in claim 1 of ‘863. The overlap in scope is evidenced by the indenopyrene compound in claim 7 of ‘863 shown below (‘863 claim 7).
PNG
media_image10.png
874
1806
media_image10.png
Greyscale
The indenopyrene compound in claim 7 is a compound of Formula 2 wherein n is 2 and L is an unsubstituted aromatic group or “biphenyl” group. ‘863 does not particularly limit the L group to biphenyl, defining the L group as an n-valent substituted or unsubstituted heterocyclic group.
‘863 teaches light-emitting devices Example 1-3 containing an indenopyrene compound that displays a high quantum yield wherein the luminance and light emitting efficiency can be improved (col 31-32, Table 1).
Therefore, 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 group L in the indenopyrene compound of ‘863 from a biphenyl group to a heteroaryl group such as a pyrimidine group in the light-emitting device of ‘863, based on the teachings of ‘863. The motivation for doing so would have been to obtain a device with displays a high quantum yield, improved luminance, and improved light emitting efficiency as taught by ‘863 (col 31-32, Table 1).
The resulting Modified Compound of ‘863 is shown below and reads on claim 1-6 and 8-11 because the Modified Compound of Sekiguchi is a compound of instant formula 1 in instant claim 1 wherein:
Ip is an indenopyrene-containing skeleton;
Ip contains a 7H-indeno[1,2-a]pyrene skeleton;
Ip contains a tert-butyl group;
Ar is a nitrogen-containing heteroaryl group;
Ar contains pyrimidine skeleton;
Fl is an indenopyrene skeleton;
Fl contains a tert-butyl group;
L1 and L2 are each independently a direct bond.
PNG
media_image11.png
200
400
media_image11.png
Greyscale
Modified Compound of ‘863
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LUCAS Q NGUYEN whose telephone number is (571)272-1199. The examiner can normally be reached Monday - Thursday 7:30 am - 5:00 pm Fridays 7:45 am to 12:00 pm.
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.
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.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786
/L.Q.N./Examiner, Art Unit 1786
Prosecution Insights