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 the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
3. Claims 1-2, 4-8, 11-12, 15-17, and 19-23 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for the compounds listed starting in paragraph [00143]-[00157], which all feature iridium (Ir) as metal M, does not reasonably provide enablement for the full scope of claim 1 and its dependents.
4. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the invention commensurate in scope with these claims. Per MPEP 2164, the claimed invention be enabled so that any person skilled in the art can make and use the invention without undue experimentation. The standard for determining whether the specification meets the enablement requirement was cast in the Supreme Court decision of Minerals Separation Ltd. V. Hyde, 242 U.S. 261, 270 (1916) which postured the question: is the experimentation needed to practice the invention undue or unreasonable?
5. Upon applying this test to claims 1-2, 4-8, 11-12, 15-17, and 19-23, it is believed that undue experimentation would be required based on the evidence regarding each of the following factors:
6. (B) The nature of the invention: Independent claim 1 requires a metal complex comprising a metal M and a ligand La coordinated to metal M wherein La has a structure represented by Formula 1 (shown below):
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and wherein the metal M is selected from a metal with a relative atomic mass greater than 40, which would encompass all of the transition metals of the periodic table.
7. (C) The state of the prior art and (E) The level of predictability in the art: The stability, structural, and chemical behaviors of metal complexes is highly influenced by several key factors including:
the nature of the metal ion; and
the oxidation state of the central metal ion; and
the nature and donor atoms of the ligands; and
overall coordination number and geometry; and
metal-ligand interactions.
(Priyanka Bhojak* and Dr. Rachna Yadav**, “Recent Advances in Metal Complex Formation and Their Physico-Chemical Characterization”, Published 2025; and Senthilkumar Muthaiah, Anita Bhatia and Muthukumar Kannan, “Stability of Metal Complexes”, Published: 05 March 2020)
8. (D) The level of one of ordinary skill: One having ordinary skill in the art would not be able to reasonably make a metal complex with ligand La, represented by Formula 1, with any metal M of a relative atomic mass greater than 40, as described in claim 1, without further guidance as it is known in the art that metal complexes have several complex factors that affect the ability to synthesize a stable compound.
9. (F) The amount of direction provided by the inventor: The specification provides no description of how to make metal complexes with ligand La, represented by Formula 1, that have metal M as anything other than iridium (Ir).
10. (G) The existence of working examples: The specification does not provide any metal complexes with ligand La, represented by Formula 1, with a metal M other than iridium (Ir).
11. (H) The quantity of experimentation needed to make or use the invention based on the content of the disclosure: One having ordinary skill in the art would not be able to reasonably predict how to appropriately synthesize a stable metal complex with ligand La, represented by Formula 1, with a metal M other than iridium (Ir) without a large amount of undue experimentation.
12. Based on the evidence regarding each of the above factors, the specification, at the time the application was filed, would not have taught one skilled in the art how to make and/or use the full scope of the claimed invention of claim 1 and its dependents without undue experimentation.
13. Claims 1-2, 4-8, 11-12, 15-17, and 19-23 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
14. Per MPEP 2163(II)(A)(3)(a)(ii), the written description requirement for a claimed genus may be satisfied through sufficient description of a representative number of species by (A) actual reduction to practice, (B) reduction to drawings, or (C) by disclosure of relevant, identifying characteristics, i.e., structure or other physical and/or chemical properties, by functional characteristics coupled with a known or disclosed correlation between function and structure, or by a combination of such identifying characteristics, sufficient to show the applicant was in possession of the claimed genus. A "representative number of species" means that the species which are adequately described are representative of the entire genus. Thus, when there is substantial variation within the genus, one must describe a sufficient variety of species to reflect the variation within the genus.
15. Independent claim 1 requires a metal complex comprising a metal M and a ligand La coordinated to metal M wherein La has a structure represented by Formula 1 (shown below):
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and wherein the metal M is selected from a metal with a relative atomic mass greater than 40, which would encompass all of the transition metals of the periodic table.
16. The description only provides compounds and examples of metal complexes with ligand La, represented by Formula 1, with metal M as iridium (Ir).
17. The limited number of examples described in the written description do not provide a representative number of species sufficient to show that applicant was in possession of the claimed genus. Therefore, the independent claim 1 and its dependents are rejected as lacking adequate written description.
18. 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.
19. Claims 2, 4-5, 7-10, 12-14, 16, 18, and 21-22 are 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.
20. Regarding claims 2, 4-5, 7-10, 12-14, and 21-22, the phrases "preferably" and, in some instances, “more preferably” render the aforementioned claims indefinite because it is unclear whether the limitations following those phrases are part of the claimed invention. See MPEP § 2173.
21. For the purposes of examination, only the clauses preceding the phrases “preferably” and “more preferably” will be interpreted as the limitations of the claimed invention.
22. Regarding claims 16 and 18, claim 16 recites the limitation “The metal complex according to claim 15, wherein Lb is, at each occurrence identically or differently, selected from the group consisting of…” and claim 18 recites the limitation “The metal complex according to claim 16, wherein the metal complex is selected from
the group consisting of Metal Complex 1 to Metal Complex 435, wherein Metal Complex 1 to Metal Complex 435 have the structure of IrLa(Lb)2, wherein the two Lb…”.
23. There is insufficient antecedent basis for the limitations in these claims. Given that claim 18 is dependent upon claim 16, claim 16 is dependent upon claim 15, claim 15 is dependent upon claim 11, and that claim 11 is dependent upon claim 1, it is unclear how the ligand Lb is defined. For the purposes of examination, the ligand Lb will be interpreted in accordance with the definitions provided for ligand Lb in claim 2.
Claim Rejections - 35 USC § 103
24. 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.
25. 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.
26. 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.
27. 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.
28. Claims 1-23 are rejected under 35 U.S.C. 103 as being unpatentable over Cai et al. (US 2020/0091442 A1) in view of Kurihara et al. (US 2018/0083206 A1).
29. Regarding claims 1-12 and 15-23, Cai teaches a metal complex of Formula 2 (Cai) (shown below, ¶ [0103]) wherein:
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R1, R3, R4, Ra, and Rb, can each independently be hydrogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl (¶ [0105]); and
metal complexes, such as those of Formula 2, bearing a fluorine atom on the dibenzo-moiety of the pyridyl-dibenzo ligand provide longer device lifetimes, better thermal stability, and higher luminous efficiency (¶ [0011]).
30. Cai discloses the following two compounds represented by Formula 2 (Cai): Compound Ir(La94)(Lb1)2 (¶ [0143]) and Compound Ir(La107)(Lb1)2 (¶ [0171], see structures below).
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31. Cai teaches the application of both aforementioned compounds in organic electroluminescent devices (see Table 1, Example 1: (Ir(La94)(Lb1)2); and Table 1, Example 6: (Ir(La107)(Lb1)2), ¶ [0191]) wherein the devices comprise:
an anode (¶ [0190]); and
a cathode (¶ [0190]); and
an organic layer disposed between the anode and cathode wherein at least one layer of the organic layer comprises a metal complex (¶ [0190]); and
the layer comprising the metal complex is a light-emitting layer (¶ [0190]); and
the light emitting layer further comprises two host compounds (Compounds EB and HB; see ¶ [0192] and Table 1, Examples 1 and 6); and
the weight of the metal complex is 8% of the total weight of the light emitting layer (see Table 1, Examples 1 and 6).
32. Cai further discloses that the ancillary ligand Lb may be selected as one of the following substituted phenyl-pyridine ligands (Lb88, see ¶ [0108] and structure below).
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33. Cai, however, does not teach or exemplify a metal complex that meets all of the limitations per claim 1, specifically wherein the 4-position of the pyridyl moiety of ligand La represented by Formula 1 is substituted with a group represented by Formula 2.
34. Kurihara teaches a metal complex of Chemical Formula 1 (Kurihara) (shown below, ¶ [0009]) wherein:
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the 4-position of the pyridyl moiety of the phenyl-pyridine ligand is substituted with a substituted or unsubstituted carbazole group.
35. Kurihara discloses the following compound represented by Chemical Formula 1 (Kurihara): Compound 100 (¶ [0074], see structure below).
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36. Kurihara teaches that the incorporation of a carbazole substituent at the 4-position of the pyridyl moiety lowers the LUMO level of the iridium-containing organometallic complex, resulting in a narrower band gap that leads to improvements in emission efficiency and a lowering of the driving voltage for organic electroluminescent devices comprising the aforementioned metal complex (¶ [0017]).
37. Kurihara additionally teaches the application of the aforementioned Compound 100 in an organic electroluminescent device and provides a comparison with Ir(ppy)3, which is identical to Compound 100 in all respects except for the presence of the carbazole substituent at the 4-position of the pyridyl moiety of one of the phenyl-pyridine ligands (see Table 1, Light-emitting element 1: Compound 100; and Table 1, Comparative light-emitting element 4: (Ir(ppy)3, ¶ [0354]).
38. Kurihara further demonstrates the improvements in emission efficiency and driving voltage for organic electroluminescent devices by using metal complexes incorporating a carbazole substituent at the 4-position of the pyridyl moiety in Table 2 (see Light-emitting element 1: Compound 100; and Comparative light-emitting element 4: (Ir(ppy)3, ¶ [0371]).
39. While Kurihara is specific towards phenyl-pyridine ligands in the discussion of the impacts of the carbazole substituent at the 4-position of the pyridyl moiety, one of ordinary skill in the pertinent art before the effective filing date of the claimed invention would be capable of recognizing that the LUMO-lowering effect of the carbazole group at the 4-position of the pyridyl moiety would not be a phenomenon exclusive to phenyl-pyridine ligands and would have a reasonable expectation of predictable results in alternative ligand systems (such as the pyridyl-dibenzofuran ligands of Compounds Ir(La94)(Lb1)2 and Ir(La107)(Lb1)2 of Cai).
40. 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 hydrogen atoms at the 4-positions of the pyridyl moieties of the pyridyl-dibenzofuran ligands of Compounds Ir(La94)(Lb1)2 and Ir(La107)(Lb1)2 of Cai with a carbazole, based on the teaching of Kurihara. The motivation for doing so would have been to narrow the band gap of the metal complex, as taught by Kurihara, and result in organic electroluminescent devices with improvements in emission efficiency and driving voltage (¶ [0017]). This modification of Compounds Ir(La94)(Lb1)2 and Ir(La107)(Lb1)2 of Cai is depicted below with Compound Cai (Kurihara Modification) and Compound Cai 2 (Kurihara Modification), respectively.
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41. Additionally, 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 atoms at the 4-positions of the pyridyl moieties of the pyridyl-dibenzofuran ligands of Compounds Ir(La94)(Lb1)2 and Ir(La107)(Lb1)2 of Cai with a carbazole, because it would have been choosing a prevalent heteroaryl substituent, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the metal complex dopant in the light-emitting layer of the organic electroluminescent device of Cai and possessing the benefits taught by Cai. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Compound Cai (Kurihara Modification) and Compound Cai 2 (Kurihara Modification), having the benefits taught by Cai (longer device lifetimes, better thermal stability, and higher luminous efficiency ¶ [0011]) in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
42. Regarding claim 1, Compound Cai (Kurihara Modification) reads on all of the limitations of Formulae 1 and 2 wherein:
M is iridium (Ir); and
X1-X8 are carbon atoms, and X1 is bonded to the pyridyl moiety of Formula 1; and
Ry represents hydrogen atoms; and
Rn is a carbazole substituent; and
Z is an oxygen atom; and
X7 is carbon atom (CRx) and Rx is a fluorine atom.
43. Regarding claim 2, Compound Cai (Kurihara Modification) reads on all of the limitations wherein:
m is equal to 1; and
n is equal to 2; and
q is equal to zero; and
Lb is represented by phenyl-pyridine (ppy) wherein Ra and Rb are all represented by hydrogen atoms.
44. Regarding claim 3, Compound Cai (Kurihara Modification) reads on all of the limitations of Formula 3 wherein:
m is equal to 2; and
R1-R8 are all represented by hydrogen atoms; and
X3-X8 are carbon atoms, and X1 is bonded to the pyridyl moiety of Formula 1; and
Ry represents hydrogen atoms; and
Rn is a carbazole substituent; and
Z is an oxygen atom; and
X7 is carbon atom (CRx) and Rx is a fluorine atom.
45. Regarding claim 4, Compound Cai (Kurihara Modification) reads on the limitation wherein Z is selected as an oxygen atom.
46. Regarding claim 5, Compound Cai (Kurihara Modification) reads on the limitation wherein X1-X8 are selected as carbon atoms (CRx), and Rx is selected as hydrogen atoms or a fluorine atom (CR7).
47. Regarding claim 6, Compound Cai (Kurihara Modification) reads on the limitation of Formula 4 wherein Rn is a carbazole substituent.
48. Regarding claim 7, Compound Cai (Kurihara Modification) reads on the limitation wherein A3-A6 in Formula 4 are each selected as CRA and RA are selected as hydrogen atoms.
49. Regarding claim 8, Compound Cai (Kurihara Modification) reads on the limitation wherein L is a single bond.
50. Regarding claim 9, Compound Cai (Kurihara Modification) reads on the limitation wherein X7 is carbon atom (CR7) and R7 is a fluorine atom.
51. Regarding claim 10, Compound Cai 2 (Kurihara Modification) reads on all of the limitations of claims 1 and 3, and further reads upon the limitation wherein:
X7 is carbon atom (CR7) and R7 is a fluorine atom; and
X8 is carbon atom (CR8) and R8 is a phenyl group.
52. Regarding claim 11, Compound Cai (Kurihara Modification) reads on the limitation wherein Rn is selected as An1, which is identical to a carbazole group.
53. Regarding claim 12, Compound Cai (Kurihara Modification) reads on the limitation wherein Ry at each occurrence is selected as hydrogen atoms.
54. Regarding claim 15, Compound Cai (Kurihara Modification) reads on the limitation wherein the ligand La is represented by La582.
55. Regarding claim 16, Compound Cai (Kurihara Modification) reads on the limitation wherein the ligand Lb is represented by Lb1.
56. Regarding claim 17, Compound Cai (Kurihara Modification) reads on the limitation wherein the ligand Lc is not required to be present as claim 2, which claim 17 depends upon, allows for q to be zero in M(La)m(Lb)n(L-c)q.
57. Regarding claim 18, Compound Cai (Kurihara Modification) reads on the limitation wherein it and the Metal Complex 31 are identical.
58. Regarding claim 19-22, Cai teaches all of the limitations of claims 19-22 (see line 31, regarding claims 1-12 and 15-23) except the inclusion of a metal complex according to claim 1.
59. While Cai generally teaches uses of the disclosed compounds (Compounds Ir(La94)(Lb1)2 and Ir(La107)(Lb1)2) in an organic electroluminescent device of claim 19, Cai does not specifically teach Compound Cai (Kurihara Modification) in an organic electroluminescent device. At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified Compound Cai (Kurihara Modification), shown above, by using the compound in an organic electroluminescent device of Cai having the structures described above as the light emitting dopant of the emission layer, based on the teaching of Cai (longer device lifetimes, better thermal stability, and higher luminous efficiency, ¶ [0011]). The modification would have been a combination of prior art elements according to known methods to yield predictable results. See MPEP 2143(I)(A)
60. The modified organic electroluminescent device of Cai comprising Compound Cai (Kurihara Modification) as the metal complex according to claim 1 reads on all of the limitations of claims 19-22 as previously delineated (see line 31, regarding claims 1-12 and 15-23).
61. Regarding claim 23, Compound Cai (Kurihara Modification) reads on the limitation wherein the metal complex is included as part of a composition.
62. Regarding claims 13-14, neither of the modified compounds Compound Cai (Kurihara Modification) nor Compound Cai 2 (Kurihara Modification) read on the limitations of claims 13-14, specifically wherein at least one of R1-R8 is not a hydrogen atom.
63. However, as shown by Formula 2 (Cai), Cai teaches that Ra and Rb of the phenyl-pyridine ancillary ligands may be substituted, and, more specifically, the phenyl-pyridine ancillary ligands may be preferably selected as Lb88 (see ¶ [0108], and see line 32, regarding claims 1-12 and 15-23).
64. Therefore, given Formula 2 (Cai) and teachings of Cai, 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 unsubstituted phenyl-pyridine ancillary ligands on the compound of Compound Cai (Kurihara Modification) with ancillary ligand Lb88, because Cai teaches this variable may be preferably selected as Lb88. This substitution is depicted below with Compound Cai 3 (Kurihara Modification).
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65. This 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 Cai 3 (Kurihara Modification) would be useful as a metal complex dopant material in the light-emitting layer of an organic electroluminescent device of Cai and possess the benefits taught by Cai (longer device lifetimes, better thermal stability, and higher luminous efficiency, ¶ [0011]). See MPEP 2143.I.(B).
66. Regarding claim 13, Compound Cai 3 (Kurihara Modification) reads on the limitations wherein:
at least one of R1-R8 is a substituted alkyl group; and
the total number of carbon atoms of the substituents R1-R8 is at least 4.
67. Regarding claim 14, Compound Cai 3 (Kurihara Modification) reads on the limitation wherein at least one of R2, R3, R6, and R7 are selected as a substituted alkyl group.
Conclusion
68. 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.
69. 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.
70. 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