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 .
Response to Amendment
In the response filed 03/23/2026, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the rejections under 35 U.S.C. 103 of claims 1, 3, 6-9, 12-17, 19-22, and 24-26 as being unpatentable over Boudreault et al. (US 2015/0236276 A1) in view of Kwong et al. (US 2013/0248832 A1), and of claims 1, 3, 6-9, 12-17, 19-23, and 25-26 as being unpatentable over Rayabarapu et al. (US 2012/0061654 A1) in view of Kwong et al. (US 2013/0248832 A1) are withdrawn by the Office.
Claims 1-20 were originally filed.
Claims 21-27 have been added.
Claims 2, 4-5, 10-11, 18, and 21 have been canceled.
Claims 1, 6, 14-15, and 19 are instantly amended.
Claims 1, 3, 6-9, 12-17, 19-20, and 22-27 are pending in the application and examined herein.
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 § 112
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.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], 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 27 and 14 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, 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.
With respect to claim 27, the claim comprises ligands which are outside the scope of parent claim 1. Specifically, claim 27 comprises ligands with an isoquinoline ring system.
Claim 14 is rejected by virtue of dependency.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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, 3, 6-7, 9, 12-13, 15-17, 19, 22-23, and 25-26 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (KR 2016/0046077 A, using the provided translation for references) and further in view of Rayabarapu et al. (US 2012/0061654 A1).
With respect to claims 1, 6, and 25-26, Kim discloses compound 166 (page 82 of the untranslated document), which is pictured below.
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However, Kim does not teach nor fairly suggest that the pyridine portion of the ligand is condensed with any additional rings.
In analogous art, Rayabarapu teaches an iridium organometallic compound for use in an organic electroluminescent device.
Rayabarapu teaches that the lowest occupied molecular orbital (LUMO) of phenylpyridine iridium complexes is normally localized on the ligand, whereas compounds comprising an aza-dibenzofuran instead of a pyridine provide better electron destabilization via the aza dibenzo-substituted ligand. Therefore, such a compound is more stable to electrons, resulting in a more stable emitter. Additionally, the compounds provide an electroluminescent device having improved lifetime and lower operating voltage (paragraph 0049).
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 an aza-dibenzofuran moiety in place of the pyridine moiety in the compound of Kim in order to provide better electron destabilization via the aza dibenzo-substituted ligand, creating a compound which is more stable to electrons, resulting in a more stable emitter, which can be used to provide an electroluminescent device having improved lifetime and lower operating voltage, as taught by Rayabarapu.
Such a compound meets the requirements of the instant claim when the compound has the formula of M(LA)3, LA has a structure of phenyl-azadibenzofuran, LB and LC are not present, M is Ir, x is 3, y and z are 0, Y is an oxygen atom, R3 and R4 represent no substitution, R2 is trimethylsilane (Si(CH3)3, TMS) and R1 is a C1 alkyl (methyl) group.
With respect to claims 3, 9, and 12-13, Kim and Rayabarapu teach the compound of claim 1, as discussed above.
Rayabarapu also teaches that preferably, compounds comprising an aza-dibenzoheterole ligand also comprise a phenylpyridine or acac (acetylacetonate) ancillary ligand (paragraph 0027). Rayabarapu also teaches that ancillary ligands function to alter the properties of the photoactive ligand (paragraph 0011).
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 phenylpyridine ligand or an acac ligand into the compound of Kim in order to alter the properties of the photoactive ligand, as taught by Rayabarapu.
Such a compound meets the requirements of instant claim 3 when the compound has the formula Ir(LA)2(LC), or when the compound has the formula Ir(LA)(LB)2.
Such a compound also meets the requirements of instant claim 9 when LB is phenylpyridine moiety, X5 is a nitrogen atom, ring D is a pyridine ring, and ring C is a benzene ring.
Such a compound also meets the requirements of instant claim 12 when LB is a phenylpyridine moiety, which is the third embodiment in the first row of page 5 of the instant claims when all X characters are carbon atoms and all R characters represent no substitution.
Such a compound also meets the requirements of instant claim 13 when LC is a acac moiety, which is instant LC1.
With respect to claim 7, Kim and Rayabarapu teach the compound of claim 1, as discussed above.
Kim also teaches that the silyl substituent on the phenyl portion of the ligand may be substituted by an ethyl group (paragraph 0070).
Such a modification produces a compound that meets the requirements of the instant claim wherein R2 has at least three more carbon atoms than R1.
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent, such as an ethyl group, from the finite list of possible substituents to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound comprising at least one silyl substituent, which can be used in an organic light-emitting device to achieve superior driving voltage, efficiency, and lifespan characteristics (paragraph 3526), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 15, Kim discloses an organic light emitting device including an anode, a cathode, and an organic layer between the anode and cathode (paragraph 0003), and the organic layer comprises an organometallic compound of chemical formula 1 (paragraphs 0009-0010), such as compound 166 (page 82 of the untranslated document), which is pictured below.
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However, Kim does not teach nor fairly suggest that the pyridine portion of the ligand is condensed with any additional rings.
In analogous art, Rayabarapu teaches an iridium organometallic compound for use in an organic electroluminescent device.
Rayabarapu teaches that the lowest occupied molecular orbital (LUMO) of phenylpyridine iridium complexes is normally localized on the ligand, whereas compounds comprising an aza-dibenzofuran instead of a pyridine provide better electron destabilization via the aza dibenzo-substituted ligand. Therefore, such a compound is more stable to electrons, resulting in a more stable emitter. Additionally, the compounds provide an electroluminescent device having improved lifetime and lower operating voltage (paragraph 0049).
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 an aza-dibenzofuran moiety in place of the pyridine moiety in the compound of Kim in order to provide better electron destabilization via the aza dibenzo-substituted ligand, creating a compound which is more stable to electrons, resulting in a more stable emitter, which can be used to provide an electroluminescent device having improved lifetime and lower operating voltage, as taught by Rayabarapu.
Such a compound meets the requirements of the instant claim when the compound has the formula of M(LA)3, LA has a structure of phenyl-azadibenzofuran, LB and LC are not present, M is Ir, x is 3, y and z are 0, Y is an oxygen atom, R3 and R4 represent no substitution, R2 is trimethylsilane (Si(CH3)3, TMS) and R1 is a C1 alkyl (methyl) group.
With respect to claim 16, Kim and Rayabarapu teach the device of claim 15, and Kim also teaches that the organic layer is an emissive layer and the compound is a dopant in the emissive layer (paragraph 2559).
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 as a dopant in the light emitting layer of a device with the claimed structure, as taught by Kim.
With respect to claim 17, Kim and Rayabarapu teach the device of claim 15, and Kim also teaches that the emissive layer comprises a host material, such as a compound of formula 11 (paragraph 2559), which includes a carbazole moiety (page 96 of the untranslated document).
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 a host material with a carbazole moiety in combination with the compound of Kim and Rayabarapu, as taught by Kim.
With respect to claim 19, Kim discloses a full-color light emitting device (a consumer product, paragraphs 2166 and 2560) comprising an organic light emitting device including an anode, a cathode, and an organic layer between the anode and cathode (paragraph 0003), and the organic layer comprises an organometallic compound of chemical formula 1 (paragraphs 0009-0010), such as compound 166 (page 82 of the untranslated document), which is pictured below.
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However, Kim does not teach nor fairly suggest that the pyridine portion of the ligand is condensed with any additional rings.
In analogous art, Rayabarapu teaches an iridium organometallic compound for use in an organic electroluminescent device.
Rayabarapu teaches that the lowest occupied molecular orbital (LUMO) of phenylpyridine iridium complexes is normally localized on the ligand, whereas compounds comprising an aza-dibenzofuran instead of a pyridine provide better electron destabilization via the aza dibenzo-substituted ligand. Therefore, such a compound is more stable to electrons, resulting in a more stable emitter. Additionally, the compounds provide an electroluminescent device having improved lifetime and lower operating voltage (paragraph 0049).
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 an aza-dibenzofuran moiety in place of the pyridine moiety in the compound of Kim in order to provide better electron destabilization via the aza dibenzo-substituted ligand, creating a compound which is more stable to electrons, resulting in a more stable emitter, which can be used to provide an electroluminescent device having improved lifetime and lower operating voltage, as taught by Rayabarapu.
Such a compound meets the requirements of the instant claim when the compound has the formula of M(LA)3, LA has a structure of phenyl-azadibenzofuran, LB and LC are not present, M is Ir, x is 3, y and z are 0, Y is an oxygen atom, R3 and R4 represent no substitution, R2 is trimethylsilane (Si(CH3)3, TMS) and R1 is a C1 alkyl (methyl) group.
With respect to claim 22, Kim and Rayabarapu teach the compound of claim 1, as discussed above.
Rayabarapu also teaches that preferably, compounds comprising an aza-dibenzoheterole ligand also comprise a phenylpyridine or acac (acetylacetonate) ligand (paragraph 0027). Rayabarapu also teaches that ancillary ligands function to alter the properties of the photoactive ligand (paragraph 0011).
Rayabarapu gives examples of suitable acac derivatives, such as those on page 24, which meet the requirements of the instant claim when z is 1, RY is H, and RX and RZ are both 2-methylpropyl.
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 acetylacetonate ligand of Rayabarapu into the compound of Kim in order to alter the properties of the photoactive ligand, as taught by Rayabarapu.
With respect to claim 23, Kim and Rayabarapu teach the compound of claim 1, and the ligand LA meets the requirements of either embodiment, (as evidenced by Formula V and VI on page 10 of Rayabarapu), as discussed above.
Claims 8 and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (KR 2016/0046077 A, using the provided translation for references) and Rayabarapu et al. (US 2012/0061654 A1) as applied above, and further in view of Boudreault et al. (US 2015/02362676 A1).
With respect to claim 8, Kim and Rayabarapu teach the compound of claim 1, as discussed above.
However, neither Kim nor Rayabarapu teach that two substituents at a location analogous to instant R3 can be joined to form a ring.
In analogous art, Boudreault teaches a nitrogenated analogue of the compound of Kim and Rayabarapu, wherein the pyridine portion of the azadibenzofuran ring system comprises at least one additional nitrogen atom (paragraphs 0016 through 0023, and Formulae I and II).
Boudreault teaches that compounds comprising just one nitrogen atom, such as the compound of Kim and Rayabarapu, can only emit light in the green to yellow range. However, compounds comprising at least one additional nitrogen atom display a very deep red color, which is a desired red color, making the compounds useful as red emitters (paragraph 0226).
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 form an analogue of the compound of Kim and Rayabarapu, having at least one additional nitrogen atom in the pyridine portion of the azadibenzofuran moiety, in order to change the emissive wavelength of the compound, and cause a significant red shift in emission color, as taught by Boudreault.
Examiner notes that Boudreault also teaches that two substituents at a location analogous to instant R3 can be joined to form a ring (paragraph 0064 and Formula II).
Such a modification produces a compound which meets the requirements of the instant claim.
Kim, Rayabarapu, and Boudreault include each element claimed, with the only difference between the claimed invention and Kim, Rayabarapu, and Boudreault being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to form an additional condensed ring on the ligand of Kim and Rayabarapu, as taught by Boudreault, in order to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound with significantly red-shifted emission, commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 24, Kim and Rayabarapu teach the compound of claim 1, as discussed above.
However, neither Kim nor Rayabarapu teach a nitrogenated analogue of the ligand discussed above.
In analogous art, Boudreault teaches a nitrogenated analogue of the compound of Kim and Rayabarapu, wherein the pyridine portion of the azadibenzofuran ring system comprises at least one additional nitrogen atom (paragraphs 0016 through 0023, and Formulae I and II).
Boudreault teaches that compounds comprising just one nitrogen atom, such as the compound of Kim and Rayabarapu, can only emit light in the green to yellow range. However, compounds comprising at least one additional nitrogen atom display a very deep red color, which is a desired red color, making the compounds useful as red emitters (paragraph 0226).
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 form an analogue of the compound of Kim and Rayabarapu, having at least one additional nitrogen atom in the pyridine portion of the azadibenzofuran moiety, in order to change the emissive wavelength of the compound, and cause a significant red shift in emission color, as taught by Boudreault.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (KR 2016/0046077 A, using the provided translation for references) and Rayabarapu et al. (US 2012/0061654 A1) as applied above, and further in view of Xia et al. (US 2015/0214494 A1).
With respect to claim 20, Kim and Rayabarapu teach the consumer product of claim 19, as discussed above.
However, neither Kim nor Rayabarapu teach any of the instantly claimed electronic apparatuses.
In analogous art, Xia teaches an organic electroluminescent device (paragraph 0003).
Xia teaches that opto-electronic devices, such as organic light emitting devices, that make use of organic materials are becoming increasingly desirable for a number of reasons including cost advantage, and inherent properties of organic materials such as their flexibility which make them well suited for fabrication on flexible substrates.
Xia goes on to teach that OLEDs are increasingly interesting technology for use in consumer products such as flat panel displays, illumination, and backlighting (paragraph 0005).
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 OLED of Kim and Rayabarapu in a consumer product such as a flat panel display, as Xia teaches that organic materials are becoming increasingly desirable for a number of reasons including cost advantage, and inherent properties of organic materials such as their flexibility which make them well suited for fabrication on flexible substrates.
Allowable Subject Matter
Claims 27 and 14 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(d) set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
With respect to claim 27, the claims require that ligand LA is represented by one of Formula Ib, Formula Ic, Formula Id, and Formula Ie, which are pictured below.
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In these formulae, relevant definitions include that R1 and R2 are selected from alkyl, cycloalkyl, and substituted variants thereof, wherein R2 has at least two more carbon atoms than R1, and R2 is not 2-methylpropyl.
A search of the prior art did not identify the claimed invention.
The closest identified art is Boudreault et al. (US 2015/0236276 A1).
With respect to claim 27, Boudreault discloses an organometallic compound comprising ligand LA138 (page 11), wherein Y1 is an sulfur atom, as pictured below.
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However, Boudreault does not teach nor fairly suggest that the substituents analogous to instant R1 and R2 are selected from alkyl, cycloalkyl, and substituted variants thereof, wherein R2 has at least two more carbon atoms than R1, and R2 is not 2-methylpropyl.
Additionally, there existed no teaching nor motivation to make such a modification in the broader prior art as of the effective filing date of the claimed invention.
Claim 14 is dependent from claim 27.
The following claim limitation drafted by the examiner and considered to distinguish patentably over the art of record in this application, Kim et al. (KR 2016/0046077 A), is presented to applicant for consideration:
“—wherein R1 and R2 are each independently selected from the group consisting of alkyl, cycloalkyl, [[silyl, germanyl,]] and substituted variants thereof; and
wherein R2 has at least two more C atoms than R1 and is not 2-methylpropyl.”
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..
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.
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
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