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 5 is objected to. The limitation “Fluorene” should be amended to “fluorene”. The limitation “Silicon (Si-Ar1Ar2)” should be amended to “silafluorene (Si-Ar1Ar2)” for better clarity as “Silicon” is an atom and should not be used to refer to the group “(Si-Ar1Ar2)”.
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.
Claims 5-9 and 17 are 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. Specifically, each of claims 5 and 17 recite Formulae 1b, 1c, and 1d. These three formulae include X in the structure. However, X is not defined anywhere in claims 5 or 17 (or in any other claim), rendering claims 5 and 17 indefinite. Claims 6-9 are included in this rejection as they are dependent on claim 5. Moreover, the specification does not appear to describe variable “X” anywhere in the specification except for when present in the structures recited in claims 5 and 17.
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.
Claims 5-9 and 17 are 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. Specifically, claims 5 and 17 recite Formulae 1b, 1c, and 1d. These three formulae include X in the structure. However, X is not defined anywhere in the claims from which claims 5 and 17 depend. Claims 6-9 are included in this rejection as they are dependent on claim 5.
Claims 15 and 16 are 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. Each of claims 15 and 16 makes reference to LA, LB, and LC, which is not recited in any of claims 1, 10, and 13, from which claims 15 and 16 depend. For purposes of further examination LA will be interpreted as L1, LB will be interpreted as L2, and LC will be interpreted as L3. Applicant may cancel the claims, amend the claims to place the claims in proper dependent form, rewrite the claims in independent form, or present a sufficient showing that the dependent claims complies with the statutory requirements.
Claim 18 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 18 is dependent from claim 14, which is dependent on claim 10, which is dependent on claim 1. None of claims 1, 10, and 14 include any chemical structures or make any reference to variables Ar1, R1, R2, L, Y, Ar2, and Ar3 which is recited in claim 18. 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.
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.
Claims 1-4 and 10-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yang et al. (J. Organomet. Chem. 2006, 691, 2767-2773, cited on Applicants information disclosure statement, filed on 7/28/25), optionally evidenced by Na et al. (Organometallics 2018, 37, 3269-3277) and/or Mao et al. (Journal of Polymer Science: Part B: Polymer Physics, 2008, 46, 547-658). Copies of Na et al. and Mao et al. are included with this Office action.
Claims 1-4: Yang et al. teaches organic light-emitting diodes which are comprised of a substrate, an anode, a hole transport region, an emission layer, an electron transport region, and a cathode. The emission layer is comprised of a host material and a phosphorescent dopant material. The phosphorescent dopant material is taught to include (4-pqz)2Ir(acac) which has the structure
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(scheme 1) where A is hydrogen and X is nitrogen. Yang et al. further teaches that this complex has a photoluminescence emission maximum of 623.5 nm, which satisfies the limitation that the phosphorescent dopant has an emission with a peak maximum wavelength greater than equal to 600 nm. Because (4-pqz)2Ir(acac) is substantially similar in structure to Applicants most preferred/exemplified iridium dopants, it would be expected that the above dopant would also have an emission wavelength maximum of greater than 600 nm as a 0.5 % doped film in PMMA as recited in claim 1. A chemical compound and its properties are inseparable. Should Applicants traverse this position, they would need to provide sufficient evidence to the contrary. While it is believed to be prima facie anticipated that the above complex anticipates Applicants peak emission maximum wavelength limitations of claim 1, Na et al. can be relied upon as an evidentiary reference. Specifically, Na et al. teaches in the abstract that the solution emission wavelengths and spectral profiles do not change substantially when compared to a 2 wt% thin films in a PMMA matrix. Additionally, Mao et al. teaches that a film of an iridium complex (structure taught in Scheme 1) at 0.94 wt% has substantially the same emission spectrum as a solution in THF [Fig. 1 and Fig. 3(b)]. For these reasons, it would be expected that the iridium complex taught by Yang et al. shown above would inherently have an emission wavelength maximum as a 0.5% doped PMMA film of greater than 600 nm.
Further, the (4-pqz)2Ir(acac) complex employed by Yang et al. is taught as having a highest occupied molecular orbital (HOMO) of -5.28 eV which satisfies the limitation that the HOMO of the dopant is lower than or equal to -5.1 eV. It is understood by one having ordinary skill in the art that a lower HOMO level means a HOMO level which is farther away from the vacuum level, that is, a HOMO level which is more negative than -5.1 eV. Paragraph 0010 of Applicants specification supports this position. The device examples of Yang et al. further includes 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) as a hole blocking layer (page 2770, right column). The compound BCP is shown in Fig. 5 of Yang et al. as having a HOMO level of -6.5 eV, which is greater than 0.2 eV lower (~ 1.1 eV lower) than the HOMO energy level of (4-pqz)2Ir(acac). The device example shown in Fig. 5 therefore anticipates all of the limitations of claim 1. Additionally, the emission wavelength maximum of (4-pqz)2Ir(acac) would also be expected to satisfy the limitations of claim 2 since 623.5 nm is greater than 610 nm, and 620 nm as required by claim 2, especially in light of the evidentiary references of Na et al. and Mao et al. The HOMO energy levels taught in Fig. 5 of Yang et al. also anticipate the HOMO energy level requirements of claims 3 and 4.
Claims 10 and 11: The iridium dopant shown in claim 1 above is a metal coordination complex having an Ir-carbon bond, thereby anticipating claims 10 and 11.
Claim 12: The iridium dopant above includes a pyrimidine chemical moiety, thereby anticipating claim 12.
Claim 13: The iridium dopant above has the formula Ir(L1)2(L3) which anticipates the formula of claim 13 with x equal to 2, y equal to 0, z equal to 1, M equal to Ir, and L1 satisfying the 7th ligand recited in claim 13 with Y2 equal to N, all other Y groups equal to C and L3 equal to the last ligand of claim 13 with Ra and Rc equal to methyl and Rb equal to hydrogen.
Claim 14: The iridium dopant above also anticipates claim 14 with L1 equal to the first ligand of claim 14 where two adjacent Ra groups are combined to form a benzene ring and L3 equal to the last ligand of claim 14 with all other variable assignments being described in claim 13 above.
Claims 15 and 16: The iridium dopant in claim 1 above has the formula Ir(LA)2(LC) with LA anticipating the second ligand of claim 16 with two adjacent RA groups being joined to form a benzene ring and LC equal to acetylacetonate, which anticipates claims 15 and 16.
Claims 1-4 and 10-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Nagai et al. (J. Mater. Chem. C 2017, 5, 527-530 plus the supporting information document) further evidenced by Na et al. (Organometallics 2018, 37, 3269-3277) and/or Mao et al. (Journal of Polymer Science: Part B: Polymer Physics, 2008, 46, 547-658). A copy of Nagai et al. and the supporting information of Nagai et al. are included in this Office action.
Claims 1-4: Nagai et al. teaches highly efficient, deep-red organic light-emitting devices. The exemplified devices include a substrate, anode, hole injection layer, a hole transport layer, an emission layer comprising two host materials which form an exciplex and the phosphorescent dopant (DPQ)2Ir(dpm), a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (page 529). The iridium dopant has the structure
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as taught in Fig 1. The electroluminescent spectrum of this dopant is shown in Fig 3(b) (inset). The peak emission of this dopant is 670 nm as taught on the right column of page 529.
While Nagai et al. does not teach that the iridium complex (DPQ)2Ir(dpm) has a peak maximum wavelength greater than or equal to 600 nm in a 0.5 % doped PMMA thin film as required by claim 1, it is submitted that the (DPQ)2Ir(dpm) dopant would be expected to satisfy this limitation given the evidentiary teachings of Na et al. and Mao et al. Specifically, Na et al. teaches that the emission wavelengths and spectral profiles in solution are substantially similar compared to a 2 wt% thin film in a PMMA matrix (abstract). Additionally, Mao et al. teaches that a film of an iridium complex (structure taught in Scheme 1) at 0.94 wt% has substantially the same emission spectrum as a solution in THF [Fig. 1 and Fig. 3(b)]. For these reasons, it would be expected that the iridium complex taught by Nagai et al. shown above would inherently have an emission wavelength maximum as a 0.5% doped PMMA film of greater than 600 nm. The devices taught by Nagai et al. have approximately 1 wt% of dopant in the emission layer, the other 99 wt% being a 1:1 mixture of the host materials. Because only 1 wt% of dopant is present in the emission layer, any ill-effects of solid state quenching of the dopant is substantially reduced or avoided all-together; meaning that the emission spectrum of the devices taught by Nagai et al. would behave as if it were a dilute solution or in a 0.5 % doped PMMA film. Therefore it would be expected that a doped film of (DPQ)2Ir(dpm) at 0.5 % in PMMA would have a peak maximum wavelength of greater than or equal to 600 nm as required by claim 1, as well as greater than 610 nm, greater than 620 nm, greater than 630 nm, and greater than 650 nm as required by claim 2. The dopant (DPQ)2Ir(dpm) is taught by Nagai et al. as having a HOMO energy level of 5.6 eV (page 12 of the supporting information). This teaching satisfies the limitation that the HOMO energy of the phosphorescent dopant is lower than or equal to -5.1 eV as required by claim 1, as well as lower than or equal to -5.2 eV, or -5.3 eV, or -5.4 eV as required by claim 3.
The compounds 4DBT46PM, 4DBT26PM, and 4DBT46TRZ, which are employed as a host material and as a hole blocking material in the hole blocking layer are taught as having a HOMO energy level of 5.96 eV, 5.97 eV, and 6.04 eV, respectively as taught in table 1 of Nagai et al. The difference in HOMO energy levels between (DPQ)2Ir(dpm) and each of the compounds 4DBT46PM, 4DBT26PM, and 4DBT46TRZ is calculated to be 0.36 eV, 0.37 eV, and 0.44 eV, respectively, which satisfies the limitation that the HOMO energy level of the hole blocking layer is at least 0.2 eV lower (more negative) than the HOMO of the phosphorescent dopant as required by claim 1, as well as at least 0.3 eV lower, and in the case of 4DBT46TRZ, 0.4 eV or lower, as required by claim 4.
Claims 10 and 11: The iridium dopant (DPQ)2Ir(dpm) is a metal coordination complex having an Ir-carbon bond, thereby anticipating claims 10 and 11.
Claim 12: The iridium dopant (DPQ)2Ir(dpm) includes a pyrazine chemical moiety, thereby anticipating claim 12.
Claim 13: The iridium dopant (DPQ)2Ir(dpm) has the formula Ir(L1)2(L3) which anticipates the formula of claim 13 with x equal to 2, y equal to 0, z equal to 1, M equal to Ir, and L1 satisfying the 10th ligand recited in claim 13 with Y5 equal to N, all other Y groups equal to C, Ra which is bonded to Y6 is phenyl, and L3 equal to the last ligand of claim 13 with Ra and Rc equal to tert-butyl, and Rb equal to hydrogen.
Claim 14: The iridium dopant (DPQ)2Ir(dpm) also anticipates claim 14 with L1 equal to the first ligand of claim 14 where two Y1 and Y2 are combined to form a benzene ring, Y4 is CRa with Ra equal to phenyl, and all other variable assignments being described in claim 13 above.
Claims 15 and 16: The iridium dopant (DPQ)2Ir(dpm) has the formula Ir(LA)2(LC) with LA anticipating the second ligand of claim 16 with two adjacent RA groups being joined to form a benzene ring and LC equal to an acetylacetonate ligand, which anticipates claims 15 and 16.
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 claims at issue 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); and 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 a nonstatutory double patenting ground provided the reference application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form 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 http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1-16, 19, and 20 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-13, 15, 19, and 20 of U.S. Patent No. 11,515,482. Although the claims at issue are not identical, they are not patentably distinct from each other. Independent claim 1 of the ‘482 patent differs from independent claim 1 only in that the ‘482 patent claims that the energy of the HOMO of the hole blocking layer is at least 0.1 eV lower than that of the dopant and the instant application recites “at least 0.2 eV lower”. A difference of at least 0.1 eV or lower inherently captures a difference of at least 0.2 eV or lower, rendering a prima facie case of anticipation. Dependent claims 2-7 of the ‘482 patent are identical to instant claims 2-7 and dependent claim 5 also satisfies the limitations of instant claims 8 and 9. Dependent claims 9-12 of the ‘482 patent reads on claims 10-13 of the instant application. Dependent claim 12 of the ‘482 patent also reads on instant claims 13 and 14 of the instant application. Claims 13 and 15 of the ‘482 patent reads on claims 15 and 16 of the instant application, respectively. Claim 19 of the ‘482 patent reads on instant claim 19. Claim 20 of the ‘482 patent is unpatentable over instant claim 20 for the same reasons as claim 1 described above.
Comment on Patentability
While all claims stand rejected, claims 5-9 and 17-19 are free of prior art rejections. While the prior art references of Yang et al. and Nagai et al. above teach a hole blocking layer, the materials employed in said layer are mutually exclusive from the specific hole blocking compounds which satisfy formula 1a through 1d as recited in claim 5 and 17, as well as the compounds recited in claim 18. Claims 6-9 are dependent on claim 5 and are also free of any prior art rejections. While the compounds employed by Nagai et al. in the hole blocking layer are close in structure to those recited in Formula Ia and Ib, there is no teaching or suggestion to modify the compounds of Nagai et al. to include an Ar1 group as required in Formulae Ia and Ib. Yang et al. does not teach an electron blocking layer and the electron blocking layer taught by Nagai et al. above employs a compound which falls outside the scope of Formula II. The closest prior art regarding the structures of claim 5 is Zeng et al. (US 2016/0028021, cited on Applicants information disclosure statement, filed on 1/18/23). While Zeng et al. teaches compounds which satisfy some of the structures of claim 5 which are employed in a hole blocking layer (Table D4), all of the working examples employ green dopants. While Zeng et al. does make mention of red dopants which may be included (the 18 structures shown on pages 67-70), none of the references which are tethered to these structures teaches that said structures have a HOMO energy level of less than -5.1 eV as required by claim 1. And of those that do teach a HOMO energy level, said HOMO energy level is less negative (lower) than -5.1 eV. For this reason, Zeng et al. is not relied upon in any prior art rejections.
Relevant Art Cited
Additional prior art documents which are relevant to Applicants invention can be found on the attached PTO-892 form.
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.
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/Robert S Loewe/Primary Examiner, Art Unit 1766