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 .
Election/Restrictions
In a requirement for election of species dated 06/28/2024, Applicant was required to choose one subspecies from the group consisting of:
Species I: a compound of General Formula I
Subspecies A: a compound of General Formula III (claims 1-2, 12, 14-15, and 17-18),
Subspecies B: a compound of General Formula IV (claims 1, 3, 12, 14-15, and 17-18),
Subspecies C: a compound of General Formula V (claims 1, 4, 12, 14-15, and 17-18),
Subspecies D: a compound of General Formula VI (claims 1, 5, 12, 14-15, and 17-18),
Subspecies E: a compound of General Formula VII (claims 1, 6, 12, 14-15, and 17-18),
Subspecies F: a compound of General Formula VIII (claims 1, 7, 12, 14-15, and 17-18),
Subspecies G: a compound of General Formula I other than those listed above (claims 1, 14, and 17),
Species II: a compound of General Formula II,
Subspecies H: a compound of General Formula IX (claims 1, 8, 13-14, 16-17, and 19),
Subspecies I: a compound of General Formula X (claims 1, 9, 13-14, 16-17, and 19),
Subspecies J: a compound of General Formula XI (claims 1, 10, 13-14, 16-17, and 19),
Subspecies K: a compound of General Formula XII (claims 1, 11, 13-14, 16-17, and 19),
Subspecies L: a compound of General Formula II other than those listed above (claims 1, 14, and 17).
Applicant’s election without traverse of Subspecies A: a compound of General Formula III in the reply filed on 08/28/2024 is acknowledged.
Subspecies A, drawn to claims 1-2, 12, 14, 17, and 20-24, is examined herein.
Response to Amendment
In the response filed 03/05/2026, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 103 of claims 1-2, 12, 14, 17, 20-22, and 24 as being unpatentable over Li et al. (US 2018/0337349 A1) in view of Li et al. (US 2019/0233455 A1) is withdrawn by the Office.
Claims 1-13, 20, 21, 23, and 24 have been amended.
Claims 1-14, 17, and 20-24 are pending in the application,
of which claims 3-11 and 13 are withdrawn from consideration.
Response to Arguments
Applicant’s arguments have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-2, 12, 14, 17, 20-22, and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Li et al. (US 2018/0337349 A1) and further in view of Otsu et al. (WO 2008/1400069 A1, using the provided translation for references).
With respect to claim 1, Li discloses the compound below (page 48).
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This compound is derived from the formula pictured below (page 10).
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Li also teaches that M is Pt(II) or Pd(II) (paragraph 0006), R1 can be a 2,6-dimethylphenyl group (second embodiment of paragraph 0046) and R2 can be absent (paragraph 0045).
Such a modification produces a compound that meets the requirements of instant General Formula I when M is Pt(II) or Pd(II), L1 and L2 are a 6-membered aryl (benzene), L3 is a 6-membered heteroaryl (pyridine), V1 is a covalent bond, V2 is absent, Y1a through Y1c are carbon atoms, Y1d is a nitrogen atom, Y2a and Y2b are carbon atoms, Y3a through Y3c are carbon atoms, Y4a through Y4c are carbon atoms, Y5a through Y5c are carbon atoms, X is an oxygen atom, X1 is a nitrogen atom, R1 through R7 are absent, Y1 is hydrogen and Y2 is a substituted aryl (2,6-dimethyl phenyl) group.
However, while Li allows for selection of a substituted phenyl group at a position analogous to instant Y2, Li only exemplifies substitution at instant Y1.
In analogous art, Otsu teaches a material for an organic electroluminescence device with short-wave luminescence, high luminous efficiency, and long luminous life (paragraph 0023) as a result of incorporating a ligand comprising a condensed, substituted imidazole moiety in a light emitting layer (paragraph 0026, Formula (6) in paragraph 0037, and paragraph 0039).
Otsu teaches that introducing an electron-absorbing substituent onto a metal complex shortens the emissive wavelength, but also shortens the luminous lifetime of the element comprising the metal complex (paragraph 0061). However, when a condensed ring ligand is used, such as phenanthridine, the electron-absorbing substituent can shorten the emissive wavelength without shortening the luminous lifetime of the element (paragraph 0065), and compounds of Otsu general equation (1), which are characterized by substitution of an aromatic or heteroaromatic ring at R1a, which is analogous to instant Y2 (paragraph 0038), are able to achieve this effect (paragraph 0064).
Examiner notes that Otsu exemplifies several possible substituted aryl group such as mesityl (A-10), 2-methylphenyl (A-105), and 2,6-dimethylphenyl (A-68).
Li and Otsu disclose an organometallic compound (a base product) upon which the claimed invention can be seen as an improvement. Otsu contains an organometallic compound (a product) that is not the same as the organometallic compound of Li, but which has been improved in the same way as the claimed invention through addition of a substituted aromatic group onto a condensed, imidazole-containing ligand at a position analogous to instant Y2. It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate a substituted aromatic ring at a location analogous to instant Y2 on the organometallic compound of Li in order to obtain the predictable result of a phenanthridine ligand comprising an electron-absorbing substituent which can shorten the emissive wavelength of the compound without shortening the luminous lifetime of the element, as taught by Otsu (MPEP 2143).
With respect to claim 2, Li and Otsu teach the compound of claim 1, and the compound is represented by General Formula III when Y3a and Y3b are carbon atoms, Y4a through Y4d are carbon atoms, and Y5a through Y5d are carbon atoms. All other characters are the same as discussed above.
With respect to claim 12, Li and Otsu teach the compound of claim 1, as discussed above.
Otsu also teaches that the substituent at R1a can be a 2-methylphenyl group, as discussed above.
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate any of the substituted aromatic rings taught by Otsu at a location analogous to instant Y2 on the organometallic compound of Li in order to obtain the predictable result of a phenanthridine ligand comprising an electron-absorbing substituent which can shorten the emissive wavelength of the compound without shortening the luminous lifetime of the element, as taught by Otsu (MPEP 2143).
Such a modification produces the first embodiment on page 24 of the instant claims, which is pictured below.
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With respect to claims 14 and 17, Li and Otsu teach the compound of claim 1, and Li also teaches an organic light emitting diode, such as a full color display, comprising the disclosed compounds (paragraph 0123).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound of Li and Otsu in a diode such as a full color display, as taught by Li.
With respect to claim 20, Li and Otsu teach the compound of claim 1, as discussed above.
Otsu also teaches that the substituent at R1a can be a substituted pyridinyl group (see for example Compound A-158).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate any of the substituted aromatic rings taught by Otsu at a location analogous to instant Y2 on the organometallic compound of Li in order to obtain the predictable result of a phenanthridine ligand comprising an electron-absorbing substituent which can shorten the emissive wavelength of the compound without shortening the luminous lifetime of the element, as taught by Otsu (MPEP 2143).
Such a modification produces a compound that meets the requirements of the instant claim.
With respect to claim 21, Li and Otsu teach the compound of claim 1, as discussed above.
Otsu also teaches that the compound can possess a methyl group at R1b in addition to a substituted aromatic substituent at R1a (see for example Compound A-203).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate any of the substituents taught by Otsu at a location analogous to instant Y1 on the compound of Li as long as the required substituted aromatic group was present at a location analogous to instant Y2 in order to obtain the predictable result of a phenanthridine ligand comprising an electron-absorbing substituent which can shorten the emissive wavelength of the compound without shortening the luminous lifetime of the element, as taught by Otsu (MPEP 2143).
Such a modification produces a compound that meets the requirements of the instant claim.
With respect to claims 22 and 24, Li and Otsu teach the compound of claim 1, and Y2 is a 2,6-dimethyl phenyl group, as discussed above.
Claim 23 is rejected under 35 U.S.C. 103 as being unpatentable over Li et al. (US 2018/0337349 A1) and further in view of Otsu et al. (WO 2008/1400069 A1, using the provided translation for references) as applied above, and further in view of Han et al. (US 2019/0334100 A1).
With respect to claim 23, Li and Otsu teach the compound of claim 1, as discussed above.
However, while within the scope of Li, neither Li nor Otsu teach that L3 should possess a substituent, R5, which is not hydrogen or deuterium, at a position ortho to instant Y3a.
In analogous art, Han teaches organometallic compounds for use in an organic light-emitting device (abstract). The compounds are unique in that they possess overlapping ring-like substituents (paragraph 0163).
Han gives a general formula by which to form the inventive compounds in Formula 1 (paragraph 0007), which is pictured below.
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This formula overlaps substantially with the compound disclosed by Li when A10 is an imidazole group (paragraph 0055, line 2), A20 is a pyridine group (paragraph 0056, line 10), A30 is a carbazole group (paragraph 0056, line 7), and A40 is benzene (paragraph 0056, line 2).
Applicant will note that Ar11 and Ar21 are located in positions ortho to the metal-ligand bond, as required by the claim.
Han also teaches that Ar11 and Ar21 are a substituted C6 aryl group (paragraph 0015, lines 1-2).
Han teaches that because the distance between Ar11 and Ar21 is short, due to π-π interaction, when applied to an organic light-emitting device, energy is easily transferred, luminance is high, and obtained color purity may be high.
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate a substituted aryl group into the compound of Li and Otsu in a position ortho to instant Y3a in order to achieve π-π interaction, and obtain an organic light-emitting device wherein energy is easily transferred, luminance is high, and high color purity is obtained, as taught by Han.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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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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/RACHEL SIMBANA/Examiner, Art Unit 1786