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 .
Election/Restrictions
In an Election of Species dated 12/20/2023, Applicant was asked to select from:
A compound comprising ligand LA having a structure of Formula I, wherein M is selected from the group consisting of:
Species I: Iridium
Species II: Palladium or platinum
Species III: Any other metal
Applicant’s election without traverse of Species I: Iridium in the reply filed on 01/04/2024 is acknowledged.
Claim 17 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 01/04/2024.
Species I, a compound comprising ligand LA having a structure of Formula I, wherein M is iridium is examined herein.
Response to Amendment
In the response filed 10/14/2025, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 102(a)(1) of claims 1-3, 5, 7, 9, and 18-19 as being anticipated by Jing et al. (WO 2019/117069 A1), the rejections under 35 U.S.C. 103 of claims 1-6, 9-14, and 18-19 as being unpatentable over Choi et al. (US 2016/0118604 A1), claim 8 as being unpatentable over Choi above and further in view of Tsai et al. (US 2012/0299468 A1), claim 15 as being unpatentable over Choi above and further in view of Thompson et al. (US 2004/0155238 A1), and of claim 20 as being unpatentable over Choi above, and further in view of Xia et al. (US 2015/0214494 A1) are withdrawn by the Office.
Claims 1, 5, 10, 18, and 20 have been amended.
Claim 21 has been added.
Claim 9 has been canceled.
Claims 1-8 and 10-21 are pending in the application.
Response to Arguments
With respect to Applicant’s argument that the instant application has an earlier effective filing date than co-pending applications 18/320,227 and 17/655,555, and the provisional nonstatutory double patenting rejection should be withdrawn, and also that the subject matter between the instant application and between applications 18/320,227 and 17/655,555 has become patentably distinct, Examiner disagrees.
Section 804.I.B.I.b.i. of the MPEP states that only once the provisional nonstatutory double patenting rejection is the only remaining rejection in an application having the earlier filing date, should the rejection be withdrawn and a patent issued. As the provisional nonstatutory double patenting rejection is not the only remaining rejection, the rejection is maintained.
Applicant's arguments with respect to the rejections over Jing et al. (WO 2019/117069 A1) have been fully considered but they are not persuasive. Applicant’s amendments do not overcome the prior art because the prior art still reads on the claimed invention.
A reinterpretation of the prior art is given below to explain how the prior art still reads on the claimed invention.
Applicant’s remaining 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 12-15 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 claims 12, 13, and 15, they all contain the option for no second ligand to be present. This is prohibited by parent claim 1, which requires that a second ligand is present. For example, no second ligand would be required when x is 3 in claim 12, or when the compound has the formula Ir(LA)3 in claims 13 and 15.
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 1-5, 10, 12-15, 18-19, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Hwang et al. (US 2017/0346025 A1).
With respect to claim 1, Hwang discloses compound 91 (page 57), comprising a ligand with a condensed cycloalkyl group, which is pictured below.
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This compound is derived from Hwang Formula 2A, which is pictured below.
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Hwang also teaches that two R11 can be joined to form a cyclopentane ring (paragraph 0136, line 3), and that the cycloalkyl group of R11 may be substituted (paragraph 0137), and examples of substituents in Formula 2A include a phenyl group (paragraph 0126 and Formula 10-1 on page 10).
This forms a compound that meets the requirements of condition 1 of the instant claim when M is iridium, ring A is fused with Formula II, ring A is a 6-membered heterocyclic (pyridine) ring fused with Formula II, and ring B is a 6-membered carbocyclic (benzene) ring, Z1 is nitrogen, Z2 is carbon, K1 and K2 are a direct bond, R2 represents disubstitution and two R2 are joined to form a dibenzofuran group, R3 represents silyl substitution, RE is monosubstitution of an aryl group, n is 1, ligand LA is coordinated to iridium through the two dashed lines, the compound comprises a second ligand that meets the requirements of condition (ii), and does not have deuterium atoms.
Hwang includes each element claimed, with the only difference between the claimed invention and Hwang 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 substituted cycloalkyl ring from each of the finite lists of possible cycloalkyl groups to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound that, when used in an organic light emitting device, results in low driving voltage, high efficiency, and long lifespan characteristics (paragraph 0656), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 2, Hwang teaches the compound of claim 1, and R2 represents disubstitution and two R2 are joined to form a dibenzofuran group, R3 represents silyl substitution, RE is monosubstitution of an aryl group, as discussed above.
With respect to claim 3, Hwang teaches the compound of claim 1, and Z1 is nitrogen and Z2 is carbon, as discussed above.
With respect to claim 4, Hwang teaches the compound of claim 1, and ring A is fused with Formula II to form ring E and n is 1, as discussed above.
With respect to claim 5, Hwang teaches the compound of claim 1, as discussed above.
Hwang also teaches that the compound may have the formula of M(L1)n1(L2)n2 (Formula 1, paragraph 0014), and that L2 may be represented by Formula 3-111 (page 35 and paragraph 0250), which is pictured below.
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This ligand meets the requirements of the instant claim.
Hwang includes each element claimed, with the only difference between the claimed invention and Hwang 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 ancillary ligand from each of the finite lists of possible ligands to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound that, when used in an organic light emitting device, results in low driving voltage, high efficiency, and long lifespan characteristics (paragraph 0656), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 10, Hwang teaches the compound of claim 1, and the ligand LA is represented by the instant second embodiment, which is pictured below.
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With respect to claims 12 and 13, Hwang teaches the compound of claim 11, and the compound has the formula Ir(LA)(LB)2 wherein x is 1, y is 2, and the oxidation state of iridium is 3, as pictured above.
With respect to claims 14 and 21, Hwang teaches the compounds of claims 13 and 1, and LB is a phenylpyridine ligand, which is the instant sixth embodiment of the claims, which is pictured below, and LC is not present.
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With respect to claim 15, Hwang teaches the compound of claim 13, as discussed above, and LB is represented by instant ligand LB1 as pictured above, and LC is not present.
With respect to claim 18, Hwang discloses an organic light emitting device (paragraph 0404) comprising an anode, a cathode (paragraph 0407), and an organic layer between the electrodes comprising a compound of Formula 1 (paragraph 0406), such as compound 91 (page 57), comprising a ligand with a condensed cycloalkyl group, which is pictured below.
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This compound is derived from Hwang Formula 2A, which is pictured below.
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Hwang also teaches that two R11 can be joined to form a cyclopentane ring (paragraph 0136, line 3), and that the cycloalkyl group of R11 may be substituted (paragraph 0137), and examples of substituents in Formula 2A include a phenyl group (paragraph 0126 and Formula 10-1 on page 10).
This forms a compound that meets the requirements of condition 1 of the instant claim when M is iridium, ring A is fused with Formula II, ring A is a 6-membered heterocyclic (pyridine) ring fused with Formula II, and ring B is a 6-membered carbocyclic (benzene) ring, Z1 is nitrogen, Z2 is carbon, K1 and K2 are a direct bond, R2 represents disubstitution and two R2 are joined to form a dibenzofuran group, R3 represents silyl substitution, RE is monosubstitution of an aryl group, n is 1, ligand LA is coordinated to iridium through the two dashed lines, the compound comprises a second ligand that meets the requirements of condition (ii), and does not have deuterium atoms.
Hwang includes each element claimed, with the only difference between the claimed invention and Hwang 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 substituted cycloalkyl ring from each of the finite lists of possible cycloalkyl groups to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound that, when used in an organic light emitting device, results in low driving voltage, high efficiency, and long lifespan characteristics (paragraph 0656), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 19, Hwang teaches the OLED of claim 18, and Hwang also teaches that the emission layer comprises a host (Table 2, page 241) such as Compound B-31 (page 243), which comprises a carbazole moiety.
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 with a carbazole moiety, as taught by Hwang.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Hwang et al. (US 2017/0346025 A1) as applied above, and further in view of Xia et al. (US 2015/0214494 A1).
With respect to claim 20, Hwang discloses an organic light emitting device (paragraph 0404) comprising an anode, a cathode (paragraph 0407), and an organic layer between the electrodes comprising a compound of Formula 1 (paragraph 0406), such as compound 91 (page 57), comprising a ligand with a condensed cycloalkyl group, which is pictured below.
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This compound is derived from Hwang Formula 2A, which is pictured below.
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Hwang also teaches that two R11 can be joined to form a cyclopentane ring (paragraph 0136, line 3), and that the cycloalkyl group of R11 may be substituted (paragraph 0137), and examples of substituents in Formula 2A include a phenyl group (paragraph 0126 and Formula 10-1 on page 10).
This forms a compound that meets the requirements of condition 1 of the instant claim when M is iridium, ring A is fused with Formula II, ring A is a 6-membered heterocyclic (pyridine) ring fused with Formula II, and ring B is a 6-membered carbocyclic (benzene) ring, Z1 is nitrogen, Z2 is carbon, K1 and K2 are a direct bond, R2 represents disubstitution and two R2 are joined to form a dibenzofuran group, R3 represents silyl substitution, RE is monosubstitution of an aryl group, n is 1, ligand LA is coordinated to iridium through the two dashed lines, the compound comprises a second ligand that meets the requirements of condition (ii), and does not have deuterium atoms.
Hwang includes each element claimed, with the only difference between the claimed invention and Hwang 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 substituted cycloalkyl ring from each of the finite lists of possible cycloalkyl groups to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound that, when used in an organic light emitting device, results in low driving voltage, high efficiency, and long lifespan characteristics (paragraph 0656), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Hwang does not teach nor fairly suggest a consumer product comprising the OLED.
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 applications such as 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 Hwang 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.
Claims 1-3, 5-6, 10, 12-15, and 18-21 are rejected under 35 U.S.C. 103 as being unpatentable over Liang et al. (CN 107266502 A, using the NEWLY provided translation for references).
With respect to claim 1, Liang discloses compound 9 (paragraph 0022 of the untranslated document), which is pictured below.
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This compound is derived from Liang general formula (I-II), which is pictured below.
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Liang also teaches that ring A is a C5 cycloalkane (paragraph 0018).
This forms a compound that meets the requirements of condition 2 of the instant claim when M is iridium, ring A is fused with a ring that is further fused with Formula II, ring A is a 6-membered heterocyclic (pyridine) ring fused with a benzene ring, and ring B is a 6-membered carbocyclic (benzene) ring, Z1 is nitrogen, Z2 is carbon, K1 and K2 are a direct bond, R2 represents no substitution, R3 represents disubstitution that is joined to form a condensed pyrrole ring, RE is monosubstitution of an aryl (phenyl) group, n is 1, ligand LA is coordinated to iridium through the two dashed lines, the compound comprises a second ligand, acetylacetonate (acac), which meets the requirements of condition (i).
Liang includes each element claimed, with the only difference between the claimed invention and Liang 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 cycloalkane from the finite list of possible cycloalkanes to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic complex for use as an organic electroluminescent material, mainly applied in the light-emitting layer of OLED devices, which has beneficial effects such as long lifespan, low driving voltage, good chemical stability and thermal stability (paragraph 0010), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 2, Liang teaches the compound of claim 1, and R2 represents no substitution, R3 represents disubstitution that is joined to form a condensed pyrrole ring, RE is monosubstitution of an aryl (phenyl) group, as discussed above.
With respect to claim 3, Liang teaches the compound of claim 1, and Z1 is nitrogen and Z2 is carbon, as discussed above.
With respect to claim 5, Liang teaches the compound of claim 1, and the second ligand is an acetylacetonate ligand, as discussed above.
With respect to claim 6, Liang teaches the compound of claim 1, and two adjacent R3 are joined to form a fused benzene ring that is further fused with ring E and ring E is a 5-membered ring, as discussed above.
With respect to claim 10, Liang teaches the compound of claim 1, and the ligand LA is represented by the structure below when Y is a carbon atom, for the reasons discussed above.
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With respect to claims 12 and 13, Liang teaches the compound of claim 11, and the compound has the formula Ir(LA)2(LC), wherein x is 2, y is 0 so that LB is not present, and z is 1, as pictured above.
With respect to claims 14 and 21, Liang teaches the compounds of claims 1 and 13, and LC is an acetylacetonate ligand, which is the first embodiment of the claim, and LB is not present.
With respect to claim 15, Liang teaches the compound of claim 13, and the compound has the formula Ir(LA)2(LC), LB is not present, and LC is represented by instant LC1-I.
With respect to claim 18, Liang discloses an organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer (organic thin film layer, paragraph 0005), and the organic layer comprises a compound of formula (I-II), such as compound 9 (paragraph 0022 of the untranslated document), which is pictured below.
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This compound is derived from Liang general formula (I-II), which is pictured below.
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Liang also teaches that ring A is a C5 cycloalkane (paragraph 0018).
This forms a compound that meets the requirements of condition 2 of the instant claim when M is iridium, ring A is fused with a ring that is further fused with Formula II, ring A is a 6-membered heterocyclic (pyridine) ring fused with a benzene ring, and ring B is a 6-membered carbocyclic (benzene) ring, Z1 is nitrogen, Z2 is carbon, K1 and K2 are a direct bond, R2 represents no substitution, R3 represents disubstitution that is joined to form a condensed pyrrole ring, RE is monosubstitution of an aryl (phenyl) group, n is 1, ligand LA is coordinated to iridium through the two dashed lines, the compound comprises a second ligand, acetylacetonate (acac), which meets the requirements of condition (i).
Liang includes each element claimed, with the only difference between the claimed invention and Liang 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 cycloalkane from the finite list of possible cycloalkanes to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic complex for use as an organic electroluminescent material, mainly applied in the light-emitting layer of OLED devices, which has beneficial effects such as long lifespan, low driving voltage, good chemical stability and thermal stability (paragraph 0010), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 19, Liang teaches the OLED of claim 18, and the organic layer further comprises the host CBP (paragraph 0118), which comprises a carbazole moiety.
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, as taught by Liang.
With respect to claim 20, Liang discloses an organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer (organic thin film layer, paragraph 0005), and the organic layer comprises a compound of formula (I-II), such as compound 9 (paragraph 0022 of the untranslated document), which is pictured below.
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This compound is derived from Liang general formula (I-II), which is pictured below.
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Liang also teaches that ring A is a C5 cycloalkane (paragraph 0018).
This forms a compound that meets the requirements of condition 2 of the instant claim when M is iridium, ring A is fused with a ring that is further fused with Formula II, ring A is a 6-membered heterocyclic (pyridine) ring fused with a benzene ring, and ring B is a 6-membered carbocyclic (benzene) ring, Z1 is nitrogen, Z2 is carbon, K1 and K2 are a direct bond, R2 represents no substitution, R3 represents disubstitution that is joined to form a condensed pyrrole ring, RE is monosubstitution of an aryl (phenyl) group, n is 1, ligand LA is coordinated to iridium through the two dashed lines, the compound comprises a second ligand, acetylacetonate (acac), which meets the requirements of condition (i).
Liang includes each element claimed, with the only difference between the claimed invention and Liang 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 cycloalkane from the finite list of possible cycloalkanes to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic complex for use as an organic electroluminescent material, mainly applied in the light-emitting layer of OLED devices, which has beneficial effects such as long lifespan, low driving voltage, good chemical stability and thermal stability (paragraph 0010), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Liang teaches that organic electroluminescent devices are suitable for use in flat panel display devices (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 Liang in a consumer product, such as a flat panel display device, as taught by Liang.
Claims 1-3, 5, 7-8, 12-15, and 18-21 are rejected under 35 U.S.C. 103 as being unpatentable over Jing et al. (WO 2019/117069 A1, using the previously provided translation for references).
With respect to claim 1, Jing discloses the compound below (paragraph 0134), which is pictured below.
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Jing also teaches that the compound may comprise an ancillary, monoanionic ligand such as acetylacetonate (acac) (paragraphs 0078 and the compounds in paragraph 0148).
Such a modification produces a compound that meets the requirements of condition (3) of the instant claim when ring A forms a direct bond to an aromatic group which is fused with Formula II, ring B is a 6-membered carbocyclic (benzene) ring, ring A is a 6-membered heterocyclic (pyridine) ring, Z1 is nitrogen, Z2 is carbon, K1 and K2 are a direct bond, R2 and R3 represent no substitution, n is 1, RE represents four alkyl groups, one of which is different, at least one of RE is alkyl, ring E has at least one carbon atom with two different RE substituents the compound comprises a second ligand, and the second ligand is acetylacetonate, which satisfies condition (i).
Jing includes each element claimed, with the only difference between the claimed invention and Jing being a lack of the aforementioned combination of ligands 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 ancillary ligand from each of the finite lists of possible ligands to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a transition metal complex that can improve solubility and aggregation resistance, as well as an organic EL device and ink composition that use the transition metal complex (paragraph 0008), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 2, Jing teaches the compound of claim 1, and R2 and R3 are not present, and RE is alkyl, as discussed and pictured above.
With respect to claim 3, Jing teaches the compound of claim 1, and Z1 is nitrogen and Z2 is carbon, as discussed above.
With respect to claim 5, Jing teaches the compound of claim 1, and the second ligand is acetylacetonate, as discussed above.
With respect to claim 7, Jing teaches the compound of claim 1, and ring A and/or ring B forms a direct bond to an aromatic moiety which is fused with Formula II to form a fused ring E wherein n is 1 and ring E is a 5-membered ring, as pictured above.
With respect to claim 8, Jing teaches the compound of claim 1, as discussed above.
Jing also teaches the compound below (paragraph 0134).
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Jing also teaches that the compound may comprise an ancillary, monoanionic ligand such as acetylacetonate (acac) (paragraphs 0078 and the compounds in paragraph 0148).
Such a modification produces a compound that meets the requirements of the instant claim when two adjacent R3 substituents of ring A are joined to form a fused aromatic structure which further form a direct bond with an aromatic moiety that is fused with ring E, wherein n is 1 and ring E is a 5-membered ring.
Jing includes each element claimed, with the only difference between the claimed invention and Jing being a lack of the aforementioned combination of ligands 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 ancillary ligand from each of the finite lists of possible ligands to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a transition metal complex that can improve solubility and aggregation resistance, as well as an organic EL device and ink composition that use the transition metal complex (paragraph 0008), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 12 and 13, Jing teaches the compound of claim 11, and the compound has the formula Ir(LA)2(LC), wherein x is 2, y is 0 and LB is not present, and z is 1.
With respect to claims 14 and 21, Jing teaches the compounds of claims 1 and 13, and LB is not present and LC is an acetylacetonate ligand, which is the first embodiment of the instant claim.
With respect to claim 15, Jing teaches the compound of claim 13, and the compound has the formula Ir(LA)2(LC), and LC is represented by instant LC1-I, as discussed above.
With respect to claim 18, Jing discloses an organic light emitting device (a blue light-emitting organic EL element, paragraph 0320) comprising an anode (ITO, paragraph 0320), a cathode (Al, paragraph 0325), and an organic layer (a light emitting layer, paragraphs 0323, 0326, and Table 2) between the electrodes and the organic layer comprises the compound below (paragraph 0134), which is pictured below.
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Jing also teaches that the compound may comprise an ancillary, monoanionic ligand such as acetylacetonate (acac) (paragraphs 0078 and the compounds in paragraph 0148).
Such a modification produces a compound that meets the requirements of condition (3) of the instant claim when ring A forms a direct bond to an aromatic group which is fused with Formula II, ring B is a 6-membered carbocyclic (benzene) ring, ring A is a 6-membered heterocyclic (pyridine) ring, Z1 is nitrogen, Z2 is carbon, K1 and K2 are a direct bond, R2 and R3 represent no substitution, n is 1, RE represents four alkyl groups, one of which is different, at least one of RE is alkyl, ring E has at least one carbon atom with two different RE substituents the compound comprises a second ligand, and the second ligand is acetylacetonate, which satisfies condition (i).
Jing includes each element claimed, with the only difference between the claimed invention and Jing being a lack of the aforementioned combination of ligands 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 ancillary ligand from each of the finite lists of possible ligands to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a transition metal complex that can improve solubility and aggregation resistance, as well as an organic EL device and ink composition that use the transition metal complex (paragraph 0008), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 19, Jing teaches the OLED of claim 18, and the organic layer further comprises host material 2 (paragraphs 0323 and 0283), which comprises a carbazole moiety, and is pictured below.
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With respect to claim 20, Jing teaches a consumer product (a display device, paragraph 0173) comprising an organic light emitting device (a blue light-emitting organic EL element, paragraph 0320) comprising an anode (ITO, paragraph 0320), a cathode (Al, paragraph 0325), and an organic layer (a light emitting layer, paragraphs 0323, 0326, and Table 2) between the electrodes and the organic layer comprises the compound below (paragraph 0134), which is pictured below.
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Jing also teaches that the compound may comprise an ancillary, monoanionic ligand such as acetylacetonate (acac) (paragraphs 0078 and the compounds in paragraph 0148).
Such a modification produces a compound that meets the requirements of condition (3) of the instant claim when ring A forms a direct bond to an aromatic group which is fused with Formula II, ring B is a 6-membered carbocyclic (benzene) ring, ring A is a 6-membered heterocyclic (pyridine) ring, Z1 is nitrogen, Z2 is carbon, K1 and K2 are a direct bond, R2 and R3 represent no substitution, n is 1, RE represents four alkyl groups, one of which is different, at least one of RE is alkyl, ring E has at least one carbon atom with two different RE substituents the compound comprises a second ligand, and the second ligand is acetylacetonate, which satisfies condition (i).
Jing includes each element claimed, with the only difference between the claimed invention and Jing being a lack of the aforementioned combination of ligands 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 ancillary ligand from each of the finite lists of possible ligands to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a transition metal complex that can improve solubility and aggregation resistance, as well as an organic EL device and ink composition that use the transition metal complex (paragraph 0008), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
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 conflicting claims 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); 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 nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) 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 www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-3, 5, 7-15, and 18-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-15, 17-18 and 20 of copending Application No. 18/320,227 (reference application) in view of Qiao et al. (US 2019/0372028 A1).
Although the claims at issue are not identical, they are not patentably distinct from each other because the limitations of co-pending ‘227 all fall within the limitations of condition 3 of the instant claimed invention in view of Qiao.
With respect to instant claim 1, claim 1 of ‘227 is drawn to a compound comprising ligand LA of formula I wherein an aromatic group which is fused with a cyclopentyl ring (analogous to instant fused ring E) is directly bonded to a bidentate ligand. However, ‘227 is drawn to any metal while the instant claims are restricted to iridium.
In analogous art, Qiao teaches organometallic iridium complexes (abstract). Qiao teaches that iridium complexes are excellent phosphorescent dyes due to their rich photophysical properties and have been widely used in organic light-emitting devices (paragraph 0003).
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 preferentially pick an iridium core for the instant claims in order to achieve an organometallic complex which is an excellent phosphorescent dye and which has rich photophysical properties.
With respect to instant claim 2, the claim is met by claim 2 of ‘227. Instant claim 3, is met by claim 5 of ‘227. Instant claim 5 is met by claim 3 of ‘227. Instant claims 7 and 8 are met by claims 1-15 of ‘227. Instant claim 9 is met by claim 1 of ‘227. Instant claim 10 is met by claims 7 and 8 of ‘227. Instant claim 11 is met by claim 9 of ‘227. Instant claims 12-15 are met by claims 10-12 of ‘227. Instant claim 18 is met by claim 17 of ‘227. Instant claim 19 is met by claim 18 of ‘227. Instant claim 20 is met by claim 20 of ‘227.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-16 and 18-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 2, 5, 7-8, 10, 12-13, 17-18, and 20 of copending Application No. 17/655,555 (reference application) in view of Qiao et al. (US 2019/0372028 A1)..
Although the claims at issue are not identical, they are not patentably distinct from each other because the limitations of co-pending ‘555 all fall within the limitations of the instant claimed invention when M is iridium.
Specifically, the compounds of ‘555 meet the requirements of instant conditions 1, 2, or 3, wherein ring A or ring B forms a direct bond to or comprises an aromatic group (ring A of ‘555), which is fused with Formula II to form a fused ring E (the cycloalkyl ring in ‘555). All the compounds of ‘555 fall within the limitations of the instant conditions. However, ‘555 is drawn to any metal while the instant claims are restricted to iridium.
In analogous art, Qiao teaches organometallic iridium complexes (abstract). Qiao teaches that iridium complexes are excellent phosphorescent dyes due to their rich photophysical properties and have been widely used in organic light-emitting devices (paragraph 0003).
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 preferentially pick an iridium core for the instant claims in order to achieve an organometallic complex which is an excellent phosphorescent dye and which has rich photophysical properties.
Instant claim 2 is met by claim 2 of ‘555. Instant claim 3 is met by claim 1 of ‘555. Instant claim 4 is met by claims 1 or 5 of ‘555. Instant claim 5 is met by claims 1 or 5 of ‘555. Instant claim 6 if met by claims 1 or 5 of ‘555. Instant claim 7 is met by claims 1 or 5 of ‘555. Instant claim 8 is met by claims 1 or 5 of ‘555. Instant claim 9 is met by claim 1 of ‘555. Instant claim 10 is met by claims 7, 8, and 10 of ‘555. Instant claim 11 is met by claim 7 of ‘555. Instant claims 12-15 are met by claims 12-13 of ‘555. Instant claim 16 is met by claim 1 of ‘555. Instant claim 18 is met by claim 17 of ‘555. Instant claim 19 is met by claim 18 of ‘555. Instant claim 20 is met by claim 20 of ‘555.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Allowable Subject Matter
Claims 11 and 16 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including 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:
Dependent claims 11 and 16 are drawn to specific embodiments of the compound of parent claim 1.
Examiner notes that none of the compounds of claims 11 and 16 comprise a silyl substituent.
A search of the prior art did not identify the claimed invention.
The closest identified prior art is Hwang et al. (US 2017/0346025 A1).
With respect to dependent claims 11 and 16, Hwang discloses an iridium compound comprising a condensed cycloalkane group according to Formula 2A, which is pictured below.
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Instant claims 11 and 16 differ from the work of Hwang because Formula 2A of Hwang requires a silyl substituent, and none of the embodiments of claims 11 and 16 comprise a silyl substituent.
Additionally, there existed no teaching nor motivation to remove the silyl substituent in the broader prior art as of the effective filing date of the claimed invention.
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..
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/RACHEL SIMBANA/Examiner, Art Unit 1786