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 .
DETAILED ACTION
Claim Objections
Claim 10 is objected to. The limitation “of compound of formula (I) is selected in the range of” as found on line 2 of claim 10 should be amended to “of the compound of formula (I) is calculated to be between” for better clarity.
Claim 12 is objected to. All of the following suggested claim amendments are due to either improper Markush claim language, awkward/confusing phrasing, and bond valency deficiencies.
The limitation “Ar5 are independently selected from substituted” should be amended to “Ar5 is independently selected from the group consisting of substituted” which is proper Markush claim language.
The limitation “spiro[fluorene-9,9’-xanthene], or a substituted” should be amended to “spiro[fluorene-9,9’-xanthene], and a substituted”.
The limitation “unsubstituted aromatic rings selected from the group comprising substituted” should be amended to “unsubstituted aromatic rings selected from the group consisting of substituted”1.
The limitation “unsubstituted hetero 5-member rings” should be amended to “unsubstituted hetero 5-membered rings”.
The limitation “unsubstituted 6-member rings” should be amended to “unsubstituted 6-membered rings”.
The limitation “unsubstituted 7-member rings” should be amended to “unsubstituted 7-membered rings”.
The limitation “substituted or unsubstituted fluorene, or a fused ring” should be amended to “substituted or unsubstituted fluorene, and a fused ring”.
The limitation “5- to 7-member rings” should be amended to “5- to 7-membered rings”.
The limitation “and the rings are selected from the group comprising (i) unsaturated” should be amended to “and the rings are selected from the group consisting of (i) unsaturated”.
The limitation “(i) unsaturated 5- to 7-member ring of a heterocycle, (ii) 5- to 6-member of an aromatic heterocycle, (iii) unsaturated 5- to 7-member ring of a non-heterocycle, (iv) 6-member ring of an aromatic non-heterocycle” should be amended to “(i) unsaturated 5-membered to 7-membered heterocyclic rings, (ii) 5- and 6-membered aromatic heterocycles, (iii) unsaturated 5- to 7-membered non-heterocyclic rings, (iv) and 6-membered aromatic non-heterocyclic rings”.
The limitation “Ar5 are selected the same or different from the group comprising H”1 should be amended to “Ar5 are independently selected from the group consisting of H”.
The limitations “C(-O)R2”, “P(-O)(R2)2”, “S(-O)R2”, and “S(-O)2R2” need to be respectively amended to “C(=O)R2”, “P(=O)(R2)2”, “S(=O)R2”, and “S(=O)2R2”.
The limitation “C3 to C18 heteroaryl, a fused ring system” should be amended to “C3 to C18 heteroaryl, and a fused ring system”.
The limitation “5- to 7-member” which appears twice in consecutive lines should be amended to “5- to 7-membered”.
The limitation “5- to 6-member of an aromatic heterocycle” should be amended to “5- and 6-membered aromatic heterocycles”.
The limitation “unsaturated 5- to 7-member ring of a non-heterocycle” should be amended to “unsaturated 5- to 7-membered non-heterocyclic rings”.
The limitation “6-member ring of an aromatic non-heterocycle” should be amended to “6-membered aromatic non-heterocyclic rings”.
The limitation “R2 is selected from H, D” should be amended to “R2 is selected from the group consisting of H, D”.
The limitation “C6 to C18 aryl, or C3 to C18 heteroaryl” should be amended to “C6 to C18 aryl, and C3 to C18 heteroaryl”.
Claim Rejections - 35 USC § 112
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.
Claim 12 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. MPEP § 2173.05(h), states “A Markush grouping is a closed group of alternatives, i.e., the selection is made from a group "consisting of" (rather than "comprising" or "including") the alternative members. Abbott Labs., 334 F.3d at 1280, 67 USPQ2d at 1196. If a Markush grouping requires a material selected from an open list of alternatives (e.g., selected from the group ‘comprising’ the recited alternatives), the claim should generally be rejected under 35 U.S.C. 112(b) as indefinite because it is unclear what other alternatives are intended to be encompassed by the claim.” There are two instances in claim 12 where the phrase “selected from the group comprising” is employed. These must be corrected in a manner consistent with proper Markush claim terminology.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 9 is rejected under 35 U.S.C. 112(d) as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 9 includes a limitation to a compound of formula (IV). Claim 1, from which claim 9 directly depends, does not recite a formula (IV). Applicant may cancel the claim, amend the claim to place the claim in proper dependent form, rewrite the claim in independent form, or present a sufficient showing that the dependent claim complies with the statutory requirements. It is suggested that Applicants amend claim 9 to be dependent from claim 5, which does recite a compound of formula (IV). In so doing, this rejection would be withdrawn.
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 of this title, 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.
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 1-8 and 10-14 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2017/0200899).
Claims 1-5, 7, and 11-14: Kim et al. teaches organic light-emitting devices. The even-numbered device examples shown in table 4 are exemplified to comprise an ITO anode, a hole injection layer which is prepared by depositing compound A15 and compound P17 in a 95:5 weight ratio, a hole transport layer consisting of compound HT3 which is a covalent compound satisfying claim 13), an emission layer comprising a host and a fluorescent dopant, an electron transport layer, an electron injection layer, and a cathode (paragraphs 0498-0501). The working examples described above satisfy all of the device limitations of 13 and 14. Compound A15 which is present as a matrix/host material in the hole injection layer, has the structure
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(page 67). This amine compound has an approximate molecular weight of 590 g/mol, which falls within the 400-2000 g/mol range of claim 11. This amine compound also satisfies formula (II) of claim 12 with T1 equal to a single bond, Ar1 equal to an unsubstituted phenyl group, T2 and T3 equal to phenylene, Ar2 equal to an unsubstituted naphthyl group, and Ar3 equal to a substituted dibenzofuran group, which is a substituted C10 heteroarylene group. Compound P17 as the p-type dopant present in the hole injection layer has the structure
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(page 120). This compound satisfies formula (I) with A1 equal to a group which satisfies formula (II) with R’ equal to CN, X1, X2, X4, and X5 equal to CR1, CR2, CR4, and CR5, respectively, with R1 and R5 equal to H, R2 and R4 equal to F, and X3 equal to N. The above compound further satisfies proviso (e) in that one of X1 to X5 is N and at least two of X1 to X5 are selected from CR1 to CR5. Variables A2 and A3 in the above compound, which are identical (thereby satisfying claim 7) satisfy formula (III) with R’ equal to CN and Ar equal to a C5 heteroaryl group which is substituted by two fluorine atoms. The above compound also satisfies formula (IV) of claim 5 with B1 equal to a group satisfying formula (V) with X1 through X5 being described above, and B3 and B5 are equal to Ar as described in formula (III) above, and B2, B4, and B6 are all R’.
In summary, the even-numbered device examples shown in Table 4 of Kim et al. satisfy all of the device and structural limitations of claim 1 with the exception that these device examples employ ITO as an anode. All of Applicants inventive examples employ ITO/Ag/ITO as the anode. Such an anode applies to the anode material as recited in claims 1-4. While the device examples of Kim et al. do not employ such an anode material, it would have been prima facie obvious to one having ordinary skill in the art to have employed such an anode given the overall teachings of Kim et al. Specifically, Kim et al. explicitly teaches that the first electrode (110), which is the anode, may have a three-layered structure of ITO/Ag/ITO (paragraph 0296). Since such an anode material is explicitly taught by Kim et al., one having ordinary skill in the art would have been motivated to employ such an anode with the reasonable expectation that an ITO/Ag/ITO anode would be a suitable choice and function effectively in said role. The anode ITO/Ag/ITO reads on all of the anode limitations of claims 1-4.
Claim 6: While the device examples of Kim et al. as described above do not include a p-type dopant in the hole injection layer which satisfies at least two of the requirements (a)-(e) as recited in claim 1, the overall teachings of Kim et al. render obvious the employment of p-type compounds which satisfy two of the requirements (a)-(e). Specifically, compound P28, which has the structure,
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(page 83) satisfies requirements (d) and (e) of claim 1 as it has two CN groups and has three N groups and two CR groups. Selection of such a compound in the manner described in the working examples would have been prima facie obvious to one having ordinary skill in the art and the motivation to employ such a compound is simply because said compound is explicitly taught. A reference may be relied upon for all that it teachings, including non-preferred/non-exemplified embodiments.
Claim 8: While the explicitly taught compounds of Kim et al. have identical groups bonded to the [3]-radialene core, Kim et al. is not limited to such compound types. Specifically, Kim et al. teaches that in the compounds of formula 3-3, which have the general structure
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, variables Y37-Y39 are independently selected from, inter alia, C(CN)(R91) where R91 is independently selected from the groups recited in paragraph 0030. It is understood by this teaching that radialene compounds having two or three different Y groups may be prepared. Such compounds would satisfy the limitation that A1 differs from A2 and A3 as recited in claim 8.
Claim 10: Applicants specification teaches compound A1 which is analogous to the compound shown above except that a C-H group is present where each pyridine nitrogen is located. The LUMO energy level of compound A1 is -4.34 eV. It is known that pyridines have a lower LUMO energy level than benzenes; therefore it would be expected that the LUMO level would be more negative than -4.34 eV, but replacing each C-H group in groups A1-A3 would certainly not lower the LUMO energy level to below -5.6 eV as evidenced by compounds A30-A34 of Applicants specification, which include pyridine groups and which all have a LUMO energy level greater than (more positive) -5.6 eV. As such, compound P17 as taught by Kim et al. satisfies the LUMO energy level requirements of claim 10.
Comment on Patentability
While all claims stand rejected, claim 9 is free of any prior art rejections. Claim 9 requires that a mixture of a compound of formula (IV) and at least one compound of formula (IVa) through (IVd) be employed in the hole injection layer. While it is known that preparing radialene compounds can produce a mixture of various isomers, with one pair of isomers having the generic structures
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. These two compounds represent one pair of E/Z isomers. These represent two of several possible E/Z isomer combinations. However, since it cannot be stated that all synthetic methods would necessarily lead to a mixture of E/Z isomers, and since purified mixtures of said compounds can be achieved, it cannot be stated with a fair degree of certainty that the radialene compounds taught and employed by Kim et al. would exist as a mixture of two or more E/Z isomeric configurations.
The Examiner expects that Applicants may try to argue unexpected results as it pertains to their claimed invention. However, any allegation of unexpected results must be commensurate in scope with the claimed invention. Currently, all working examples employ one type of anode (ITO/Ag/ITO) and independent claim 1 refers to an anode in a much broader fashion. All working examples also require an amine-based matrix material which is present in the hole injection layer. Additionally, the improvements as shown in Applicants working examples employ a compound of formula (I) having a LUMO energy level between -4.3 eV and -5.6 eV.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT S LOEWE whose telephone number is (571)270-3298. The examiner can normally be reached on Monday-Friday from 8 AM to 5 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski, can be reached at telephone number 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Robert S Loewe/Primary Examiner, Art Unit 1766
1 This portion of claim 12 is also rejected under 112(b).