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 .
Priority
2. Acknowledgment is made of applicant's claim for foreign priority based on an
application filed in China on March 29, 2022.
3. Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C.
119(a)-(d) prior to declaration of an interference, a certified English translation of the
foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and
41.202(e).
4. Failure to provide a certified translation may result in no benefit being accorded
for the non-English application.
Information Disclosure Statement
5. The references provided in the Information Disclosure Statement filed on March
27, 2023 have been considered. Signed copies of the corresponding 1449 forms have
been included with this office action.
Claim Rejections - 35 USC § 112
6. 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.
7. Claims 1-3, 5-8, 11-14, and 17-24 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 claims contain 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 inventors, at the time the application was filed, had possession of the claimed invention.
8. 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.
9. 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.
10. The description only provides compounds and examples of metal complexes with
ligand La, represented by Formula 1, with metal M as iridium (Ir) (see metal complexes 134 and 150: ¶ [00137]-[00157]; and device examples 1-2: ¶ [00158]-[00175],
see also Tables 1-2).
11. 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 (2-3, 5-8, 11-14, and 17-24) are rejected as lacking adequate written description.
12. 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.
13. Claims 3-13, 15-16, 19, and 22-23 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.
14. Regarding claims 3, 5-13, 15-16, 19, and 22-23, 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.
15. 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.
16. Claim 4 recites the limitation “The metal complex according to claim 1, wherein the metal complex Ir(La)m(Lb)3-m has a structure represented by Formula 3…”
17. There is insufficient antecedent basis for the limitation in this claim. Given
that claim 4 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 definition provided for ligand Lb in claim 3.
Claim Rejections - 35 USC § 103
18. 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.
19. 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.
20. 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.
21. 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.
22. Claims 1-24 are rejected under 35 U.S.C. 103 as being unpatentable over
Tsai et al. (US 2021/0054010 A1; hereinafter “Tsai”) in view of Cai et al. (US 2020/0091442 A1; hereinafter “Cai”), Babudri et al. (“Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom.” Chemical Communications, (2007), pgs. 1003-1022; hereinafter “Babudri”), and Zhao et al. (CN 111808142 A; hereinafter “Zhao”).
23. Regarding claims 1-14 and 16-19, Tsai teaches organometallic complexes comprising a ligand of Formula I (Tsai, see below, [Abstract]) wherein:
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ring A can be selected as pyridine (Z1 is a carbon atom and Z2 is a nitrogen atom, ¶ [0056]); and
RA, RB, RC, and RD can be selected as fluorine, alkyl groups, or aryl groups (¶ [0044]-[0046], [0054]); and
Y can be selected as an oxygen atom or a sulfur atom (¶ [0055]); and
X1-X8 can be selected as carbon atoms (¶ [0059]); and
Ring D can be selected as a substituted or unsubstituted 6-membered aromatic ring (¶ [0063]).
24. Tsai teaches organic electroluminescent devices, comprising organometallic complexes with ligand of Formula 1 as dopants in the light emitting layer, that exhibit narrower FWHM and higher efficiencies (¶ [0168]-[0171]; see also Tables 1-2).
25. Tsai specifically discloses the following iridium complex (LA1-1-9(LB28)2; ¶ [0093], see structure below) which reads on the limitations of Formulae 1 and 2 of claim 1 of
the instant application, but fails to include the following wherein:
Y2 and/or Y3 are selected from CRy and Ry is fluorine; and
at least one of X1-X8 is selected from CRx and Rx is cyano or fluorine.
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26. Cai teaches organometallic complexes of Formula 2 (Cai) (shown below, ¶ [0103]) wherein:
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R1, R3, R4, Ra, and Rb, can each independently be hydrogen, a halogen, 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 (Cai), bearing a fluorine atom (at the position circled) on the dibenzo-moiety of the pyridyl-dibenzo ligand provide longer device lifetimes, better thermal stability, and higher luminous efficiency (¶ [0011]).
27. Cai discloses the following compound represented by Formula 2 (Cai):
Compound Ir(La94)(Lb1)2 (¶ [0134]-[0144], see structure below) and discloses an organic electroluminescent device comprising Compound Ir(La94)(Lb1)2 as a dopant in the light emitting layer (see Example 1 in Tables 1 and 2).
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28. Additionally, Cai teaches that devices comprising other iridium complexes as dopants in the light emitting layer (¶ [0192]; see Compounds D, E, F, G) wherein the fluorine substituent is transposed to different positions on the pyridyl-dibenzofuranyl ligand exhibit diminished lifetimes relative to the device comprising Compound Ir(La94)(Lb1)2 (see Comparative Examples 4-7 in Tables 1 and 2; ¶ [0198]).
29. 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 atom on the dibenzofuranyl moiety of compound LA1-1-9(LB28)2 of Tsai with a fluorine atom at position X7 (per Formula 1 of claim 1 of the instant application), based on the teaching of Cai. The motivation for doing so would have been to improve device lifetime, as taught by Cai.
30. 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 atom on the dibenzofuranyl moiety of compound LA1-1-9(LB28)2 of Tsai with a fluorine atom at position X7 (per Formula 1 of claim 1 of the instant application), because it would have been choosing among the preferable substituents for RC of Tsai, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the dopant in the light emitting layer of the organic electroluminescent device of Tsai and possessing the benefits taught by Tsai. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 1 of Tsai having the benefits taught by Tsai in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
31. The compound of Tsai, as modified by Cai, is shown below, wherein the fluorine substitution is indicated with a circle.
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32. Tsai, as modified by Cai, fails to teach Y2 and/or Y3 (per Formula 1 of the instant application) as CRy wherein Ry is a fluorine atom as required by claim 1. Babudri teaches electroluminescent devices comprising fluorinated compounds that obtain higher lifetimes, and that specifically replacing C-H bonds with C-F bonds may enhance photoluminescent efficiency in an electroluminescent organometallic compound (abstract; pg. 1003, Introduction, second paragraph; pg. 1008, second column, sections i-v).
33. Tsai, as modified by Cai and Babudri, fails to teach a specific site of modification regarding the replacement of a C-H bond with a C-F bond. Zhao teaches substantially identical compounds (see Chemical Formula 1, pg. 1) to Tsai for use in OLEDs, as shown by J001 (pg. 2) and J087 (pg. 7; see structures below).
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34. The compounds J001 and J087 are identical except for wherein J087 contains a fluorine substituent in the meta-position with respect to the Ir-N bond of the pyridyl moiety. As shown by the data in Table 2 (pgs. 15-16), the device comprising J087 obtains improved driving voltage and current efficiency in comparison to the device comprising J001.
35. 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 a fluorine atom in the meta-position of the pyridyl moiety with respect to the Ir-N bond of LA1-1-9(LB28)2 (Tsai: Cai Modification), as shown by compound J087 of Zhao, based on the teachings of Babudri and Zhao. The motivation for doing so would have been to obtain a device with improved lifetime and enhanced photoluminescence efficiency, as taught by Babudri, and improved driving voltage and current efficiency, as taught by Zhao.
36. 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 atom on the pyridyl moiety of compound LA1-1-9(LB28)2 (Tsai: Cai Modification) with a fluorine atom at position Y3 (per Formula 1 of claim 1 of the instant application), because it would have been choosing among the preferable substituents for RA of Tsai, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the dopant in the light emitting layer of the organic electroluminescent device of Tsai and possessing the benefits taught by Tsai. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 1 of Tsai having the benefits taught by Tsai in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
37. The compound of Tsai, as modified by Cai, Babudri, and Zhao, is shown below, wherein the fluorine substitution of Baubdri and Zhao is indicated with a circle.
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38. Per claim 1, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on all the limitations of Formulae 1 and 2 wherein:
M is iridium (Ir); and
Z is an oxygen atom; and
Y1-Y4 are CRy wherein Y2 is substituted with a trideutero-methyl group and Y3 is substituted with a fluorine atom; and
X1-X8 are CRx; and
X1 is a carbon atom joined to the pyridyl moiety; and
X2 is a carbon atom forming a metal carbon bond; and
X7 is a carbon atom with a fluorine substituent; and
X8 is a carbon atom with a substituent Ar represented by Formula 2; and
The substituent Ar is a biphenyl group wherein Ar2 is an aromatic ring with 6 ring atoms, Ar1 is an aromatic ring with 6 ring atoms, and the total number of ring atoms in Ar1 and Ar2 is greater than 8; and
a of Formula 2 is an integer equal to 1; and
Y1, Y4, X3-X6, Ra1, and Ra2 are carbon atoms with hydrogen atoms as substituents.
39. Per claim 2, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications ) reads on all the limitations of Formula 1a as described previously.
40. Per claim 3, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications ) reads on all the limitations wherein:
the metal complex has the general of M(La)m(Lb)n(Lc)q; and
ligand La is as previously defined and m is an integer equal to 1; and
ligand Lb is represented by
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, wherein Ra and Rb are hydrogen atoms and substituted alkyl groups, and n is an integer equal to 2; and
ligand Lc is not required to be present (q is equal to zero).
41. Per claim 4, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications ) reads on all the limitations of Formula 3 of the instant application wherein:
ligand La is as previously defined and m is an integer equal to 1; and
R1, R3-R6, and R8 are all hydrogen atoms; and
R2 and R7 are trideutero-methyl groups.
42. Per claim 5, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein Z is selected as an oxygen atom.
43. Per claim 6, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein a of Formula 2 is an integer equal to 1.
44. Per claim 7, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
Y1-Y4 are CRy; and
Y2 is substituted with a trideutero-methyl group; and
Y3 is substituted with a fluorine atom; and
Y1 and Y4 are substituted with hydrogen atoms.
45. Per claim 8, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
Y1-Y4 are CRy; and
Y2 is substituted with a trideutero-methyl group; and
Y3 is substituted with a fluorine atom; and
Y1 and Y4 are substituted with hydrogen atoms.
46. Per claim 9, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
X7 is a carbon atom with a fluorine substituent; and
X8 is a carbon atom with a substituent Ar represented by Formula 2; and
The substituent Ar is a biphenyl group wherein Ar2 is phenyl, Ar1 is phenyl, and the total number of ring atoms in Ar1 and Ar2 is greater than 8; and
a of Formula 2 is an integer equal to 1.
47. Per claim 10, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
X7 is a carbon atom with a fluorine substituent; and
X8 is a carbon atom with a substituent Ar represented by Formula 2; and
The substituent Ar is a biphenyl group wherein Ar2 is phenyl, Ar1 is phenyl, and the total number of ring atoms in Ar1 and Ar2 is greater than 8; and
a of Formula 2 is an integer equal to 1.
48. Per claim 11, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein Ra1 and Ra2 are all hydrogen atoms
49. Per claim 12, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
Ar2 is an aromatic ring with 6 ring atoms; and
Ar1 is an aromatic ring with 6 ring atoms; and
the total number of ring atoms in Ar1 and Ar2 is greater than 8 and less than 30.
50. Per claim 13, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
Ar2 is a benzene ring; and
Ar1 is a benzene ring.
51. Per claim 14, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein Ar is selected as
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.
52. Per claim 16, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
R2 and R7 are substituted alkyl groups having 1 carbon atom (trideutero-methyl groups).
53. Per claim 17, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein ligand La is selected as La726 (see structure below).
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54. Per claim 18, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein ligand Lb is selected as Lb30 (see structure below).
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55. Per claim 19, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein the metal complex has the structure IrLa(Lb)2 and La is represented by La726 and Lb is represented by Lb30.
56. Regarding claims 20-24, Tsai teaches organic electroluminescent devices comprising:
an anode (ITO, ¶ [0168]); and
a cathode (Al, ¶ [0168]); and
an organic layer disposed between the anode and cathode wherein at least one layer of the organic layer comprises a metal complex (¶ [0168]); and
the organic layer comprising the metal complex is a light-emitting layer (¶ [0168]; and see Table 1); and
the light emitting layer further comprises two host compounds (Compounds H1 and H2; see ¶ [0168] and Table 1); and
the weight of the metal complex is 12% of the total weight of the light emitting layer (see ¶ [0168] and Table 2, Inventive Example); and
a compound combination comprising a metal complex (wherein the light emitting layer is interpreted as the compound combination).
57. Tsai teaches an anode, a cathode, and an organic layer and the compound is in the organic layer as discussed above. Tsai does not disclose a device comprising LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) as the metal complex dopant in the light emitting layer. It would have been obvious to one of ordinary skill in the pertinent art prior to the effective filing date of the claimed invention to use the compound LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) in the light emitting organic layer with the device structure of Tsai.
58. One of ordinary skill in the art would have been motivated to produce additional devices comprising compound LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) as the metal complex dopant in the light emitting layer having the benefits taught by Tsai 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).
59. Regarding claim 15, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) fails to read on the limitation wherein the total number of carbon atoms in all of R1 to R4 and/or R5 to R8 is at least 4.
60. Tsai does teach, however, that the ancillary ligand LB can be selected as the following substituted phenyl-pyridine ligand LB142 (¶ [0079] and see structure below).
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61. Therefore, given the teachings of Tsai, 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 phenyl-pyridine ancillary ligand on the compound LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) with ancillary ligand LB142, because Tsai teaches that the ancillary ligand may be preferably selected as LB142. This substitution is depicted below with LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications 2).
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62. 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 LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications 2) would be useful as a metal complex dopant material in the light-emitting layer of an organic electroluminescent device of Tsai and possess the benefits taught by Tsai (narrower FWHM and higher efficiencies (¶ [0168]-[0171]). See MPEP 2143.I.(B).
Conclusion
63. 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.
64. 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.
65. 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.
66. 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.
/B.J.C./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786
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