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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 07/03/2025 has been entered.
This office action is in response to the amendment filed 07/03/2025, which amends claims 1, 10, 13, 15, 17, and 19, cancels claims 2 and 9, and adds claims 22-25. Claims 1, 3-8, 10, and 13-25 are pending in the application.
Response to Amendment
In the response filed 07/03/2025, the claims were amended.
These amendments are hereby entered.
Response to Arguments
Applicant's arguments filed 07/03/2025 have been fully considered but they are not persuasive.
With respect to Applicant’s argument that Tsai’s disclosure of an ancillary ligand is improper because the prior art is primarily drawn to osmium complexes, Examiner disagrees.
The work of Kita and the work of Tsai are of analogous art. To determine whether two pieces of art are of analogous art, it must be determined (1) whether the reference is from the same field of endeavor as the claimed problem (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem face by the inventor (even if it is not in the same field of endeavor as the claimed invention. It is not necessary for the prior art to fulfill both tests to qualify as analogous art. In the instant case, Kita and Tsai are both drawn to organometallic complexes in OLED devices (test 1) and are of analogous art (MPEP 2141.01(a)).
Further, the test of obviousness is what the combined teachings of the references would have suggested to one of ordinary skill in the art, and all teachings in the prior art must be considered (MPEP 2143.01). While Kita is generally drawn to iridium complexes and Tsai is generally drawn to osmium complexes, Tsai contains a crucial teaching for iridium complexes which cannot be ignored and would suggest to one of ordinary skill in the art that the disclosed ancillary ligands have beneficial properties when used in iridium complexes. Specifically, Tsai teaches that incorporation of these ligands into iridium complexes improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and their EQE. Thus, a person having ordinary skill in the art would modify an iridium complex to have the ancillary ligand of Tsai in order to achieve improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and their EQE, as taught by Tsai.
For at least these reasons, the rejections are respectfully maintained.
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(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 14 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
With respect to claim 14, the preamble of the claim is drawn to “The compound of claim 9”, however, claim 9 is now canceled. MPEP 2260.01 teaches us that if a base claim has been canceled, a claim which depends thereon should be rejected as indefinite.
For the purpose of examination, the claim will be interpreted as dependent from claim 1, as canceled claim 9 was previously dependent from claim 1.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
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.
Claims 1, 3, 6-7, 10, 13-16, 19-21, and 25 are rejected under 35 U.S.C. 103 as being unpatentable over Kita et al. (JP 2003/109758 A, using the attached translation for references), in view of Tsai et al. (US 2015/0129840 A1).
With respect to claim 1, Kita discloses Compound 27 (page 15 of the untranslated document), which is pictured below.
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The phenylpyridine ligand of compound 27 meets the requirements of condition (1) of instant Formula I when n is 2, A is a 6-membered aromatic ring, R represents no substitution, Z1 is CR1, Z2 is CR2, Z3 is CR3, Z4 is CR4 and Z5 is CR5, R5 is aryl (phenyl), all other R characters are hydrogen atoms, and the ligand is coordinated to iridium.
However, while Kita teaches that the compound may comprise an ancillary ligand, Kita does not teach nor fairly suggest one of the instant LB ligands.
In analogous art, Tsai teaches novel ancillary ligands for metal complexes (paragraph 0018). Tsai teaches that incorporation of these ligands into iridium complexes improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and their EQE (external quantum efficiency) (paragraph 0018).
Tsai gives examples of such ancillary ligands on pages 7-10, one of which, L131, is pictured below.
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This ancillary ligand meets the requirements of the first embodiment of LB of the instant claim when all X groups are carbon atoms, Ra and Rc represent no substitution, and Rb is alkyl.
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 ancillary ligand of Tsai as the ancillary ligand in the compound of Kita in order to obtain improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and EQE, as taught by Tsai.
With respect to claim 3, Kita and Tsai teach the compound of claim 1, and Z1 is CH, Z5 is CR5 and R5 is aryl, as discussed above.
With respect to claim 6, Kita and Tsai teach the compound of claim 1, and ring A is benzene, as pictured above.
With respect to claim 7, Kita and Tsai teach the compound of claim 1, and ligand LA is a phenylpyridine ligand which is the first embodiment of the claim, as pictured above.
With respect to claim 10, Kita and Tsai teach the compound of claim 1, and the compound has the formula Ir(LA)2(LB), as discussed above.
Kita also teaches that n is 1 and m is 2 when Me is iridium (paragraph 0051, lines 12-13).
Such a modification produces a compound with the general formula of Ir(LA)(LB)2.
Kita includes each element claimed, with the only difference between the claimed invention and Kita being this number of ancillary 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 modify the compound to have one or two ancillary ligands and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a metal complex with a dihedral angle of 9 degrees or more and less than 90 degrees, which exhibits phosphorescence in the blue chromaticity region that is slightly shorter than conventional wavelengths when used as a dopant and yields an organic electroluminescence element with highly efficient blue emission (paragraph 0037), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Further, 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 ancillary ligand of Tsai as the ancillary ligand in the compound of Kita in order to obtain improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and EQE, as taught by Tsai.
With respect to claim 13, Kita and Tsai teach the compound of claim 1, and ligand LB is selected as the eleventh embodiment of the claim, which is pictured below, when Ra and Rc represent no substitution, and Rb is alkyl, as discussed above.
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With respect to claim 14, Kita and Tsai teach the compound of claim 1, as discussed above.
Tsai also teaches the ancillary ligand may be L134, which is pictured below.
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This ligand meets the instant requirements when all X characters are unsubstituted carbon atoms, Ra and Rc represent no substitution and Rb is alkyl.
Further, 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 any of the ancillary ligands of Tsai as the ancillary ligand in the compound of Kita in order to obtain improved sublimation of the resulting iridium complexes, color spectrum phosphorescence by the iridium complexes, and their EQE, as taught by Tsai.
With respect to claim 15, Kita discloses an organic light emitting element (paragraph 0179), comprising an anode, a cathode, and an organic layer between the electrodes comprising a light emitting layer (paragraph 0179), and the light emitting layer comprises Compound 27 (page 15 of the untranslated document), which is pictured below.
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The phenylpyridine ligand of compound 27 meets the requirements of condition 1 of instant Formula I when n is 2, A is a 6-membered aromatic ring, R represents no substitution, Z1 is CR1, Z2 is CR2, Z3 is CR3, Z4 is CR4 and Z5 is CR5, R5 is aryl (phenyl), all other R characters are hydrogen atoms, and the ligand is coordinated to iridium.
However, while Kita teaches that the compound may comprise an ancillary ligand, Kita does not teach nor fairly suggest one of the instant LB ligands.
In analogous art, Tsai teaches novel ancillary ligands for metal complexes (paragraph 0018). Tsai teaches that incorporation of these ligands into iridium complexes improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and their EQE (external quantum efficiency) (paragraph 0018).
Tsai gives examples of such ancillary ligands on pages 7-10, one of which, L131, is pictured below.
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This ancillary ligand meets the requirements of the first embodiment of LB of the instant claim when all X groups are carbon atoms, Ra and Rc represent no substitution, and Rb is alkyl.
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 ancillary ligand of Tsai as the ancillary ligand in the compound of Kita in order to obtain improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and EQE, as taught by Tsai.
With respect to claim 16, Kita and Tsai teach the OLED of claim 15, and Kita teaches that the organic layer is the emissive layer, as discussed above, and the compound is an emissive dopant (paragraph 0259).
With respect to claim 19, Kita discloses a consumer product (a full color display, paragraph 0034, line 1), comprising an anode, a cathode, and an organic layer between the electrodes comprising a light emitting layer (paragraph 0179), and the light emitting layer comprises Compound 27 (page 15 of the untranslated document), which is pictured below.
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The phenylpyridine ligand of compound 27 meets the requirements of condition 1 of instant Formula I when n is 2, A is a 6-membered aromatic ring, R represents no substitution, Z1 is CR1, Z2 is CR2, Z3 is CR3, Z4 is CR4 and Z5 is CR5, R5 is aryl (phenyl), all other R characters are hydrogen atoms, and the ligand is coordinated to iridium.
However, while Kita teaches that the compound may comprise an ancillary ligand, Kita does not teach nor fairly suggest one of the instant LB ligands.
In analogous art, Tsai teaches novel ancillary ligands for metal complexes (paragraph 0018). Tsai teaches that incorporation of these ligands into iridium complexes improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and their EQE (external quantum efficiency) (paragraph 0018).
Tsai gives examples of such ancillary ligands on pages 7-10, one of which, L131, is pictured below.
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This ancillary ligand meets the requirements of the first embodiment of LB of the instant claim when all X groups are carbon atoms, Ra and Rc represent no substitution, and Rb is alkyl.
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 ancillary ligand of Tsai as the ancillary ligand in the compound of Kita in order to obtain improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and EQE, as taught by Tsai.
With respect to claim 20, Kita and Tsai teach the consumer product of claim 19, and Kita also teaches that OLEDs are useful as a light for interior or exterior illumination (in lighting applications, paragraph 0008).
With respect to claim 21, Kita and Tsai teach the compound of claim 1, and the ancillary ligand of Tsai meets the requirements of the instant claim when all X characters are carbon atoms, Ra and Rc represent no substitution and Rb is alkyl, as discussed above.
With respect to claim 25, Kita and Tsai teach the compound of claim 1, and the compounds has the formula Ir(LA)2(LB), as discussed above.
Claims 1, 5-7, 10, 13-16, 19-21, and 25 are rejected under 35 U.S.C. 103 as being unpatentable over Ise et al. (US 2012/0126692 A1) in view of Tsai et al. (US 2015/0129840 A1).
With respect to claim 1, Ise discloses Compound TM-20 (page 32), which is pictured below.
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The phenylpyridine ligand of compound TM-20 meets the requirements of condition (3) of instant Formula I when A is a 6-membered aromatic (benzene) ring, R represents an aryl (phenyl) group, Z1 is CR1, R1 is an alkyl (methyl) group, Z2 is CR2, Z3 is CR3, R3 is aryl (phenyl) group, Z4 is CR4, and Z5 is CR5, all other R characters are hydrogen atoms, and the ligand is coordinated to iridium.
Compound TM-20 is derived from Ise Formula (T-1), which is pictured below.
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In this formula, X-Y is any ancillary ligand (paragraph 0013, line 32).
However, while Ise teaches that the compound may comprise an ancillary ligand, Ise does not teach nor fairly suggest one of the instant LB ligands.
In analogous art, Tsai teaches novel ancillary ligands for metal complexes (paragraph 0018). Tsai teaches that incorporation of these ligands into iridium complexes improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and their EQE (external quantum efficiency) (paragraph 0018).
Tsai gives examples of such ancillary ligands on pages 7-10, one of which, L131, is pictured below.
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This ancillary ligand meets the requirements of the first embodiment of LB of the instant claim when all X groups are carbon atoms, Ra and Rc represent no substitution, and Rb is alkyl.
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 ancillary ligand of Tsai as the ancillary ligand in the compound of Ise in order to obtain improved sublimation of the resulting iridium complexes, color spectrum, phosphorescence by the iridium complexes, and their EQE, as taught by Tsai.
With respect to claim 5, Ise and Tsai teach the compound of claim 1, and Z3 is CR3, R3 is aryl, Z1 is CR1 and R1 is alkyl, as discussed above.
With respect to claim 6, Ise and Tsai teach the compound of claim 1, and ring A is benzene, as pictured above.
With respect to claim 7, Ise and Tsai teach the compound of claim 1, and ligand LA is a phenylpyridine ligand which is the first embodiment of the claim.
With respect to claim 10, Ise and Tsai teach the compound of claim 1, and the compound has the formula Ir(LA)2(LB), as discussed above.
Ise Formula (T-1) also teaches that m is 1 and n is 2 (paragraph 0013, lines 32-34).
Such a modification produces a compound with the formula Ir(LA)(LB)2.
Ise includes each element claimed, with the only difference between the claimed invention and Ise being this number of ancillary 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 modify the compound to have one or two ancillary ligands and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a metal complex which, when used in an organic light emitting device, results in high external quantum efficiency and excellent durability as well as steady performance even in uses for which drive durability in high-temperature conditions are required (paragraph 0027), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Further, 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 ancillary ligand of Tsai as the ancillary ligand in the compound of Ise in order to obtain improved sublimation of the resulting iridium complexes, color spectrum of phosphorescence by the iridium complexes, and EQE, as taught by Tsai.
With respect to claim 13, Ise and Tsai teach the compound of claim 1, and ligand LB is selected as the eleventh embodiment of the claim, which is pictured below, when Ra and Rc represent no substitution, and Rb is alkyl, as discussed above.
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With respect to claim 14, Ise and Tsai teach the compound of claim 1, as discussed above.
Tsai also teaches the ancillary ligand may be L134, which is pictured below.
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This ligand meets the instant requirements when all X characters are unsubstituted carbon atoms, Ra and Rc represent no substitution and Rb is alkyl.
Further, 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 any of the ancillary ligands of Tsai as the ancillary ligand in the compound of Kita in order to obtain improved sublimation of the resulting iridium complexes, color spectrum phosphorescence by the iridium complexes, and their EQE, as taught by Tsai.
With respect to claim 15, Ise discloses an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the electrodes comprising a light emitting layer (paragraph 0153), and the light emitting layer comprises the inventive organometallic (paragraph 0169) Compound TM-20 (page 32), which is pictured below.
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The phenylpyridine ligand of compound TM-20 meets the requirements of condition 3 of instant Formula I when A is a 6-membered aromatic (benzene) ring, R represents an aryl (phenyl) group, Z1 is CR1, R1 is an alkyl (methyl) group, Z2 is CR2, Z3 is CR3, R3 is aryl (phenyl) group, Z4 is CR4, and Z5 is CR5, all other R characters are hydrogen atoms, and the ligand is coordinated to iridium.
Compound TM-20 is derived from Ise Formula (T-1), which is pictured below.
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In this formula, X-Y is any ancillary ligand (paragraph 0013, line 32).
However, while Ise teaches that the compound may comprise an ancillary ligand, Ise does not teach nor fairly suggest one of the instant LB ligands.
In analogous art, Tsai teaches novel ancillary ligands for metal complexes (paragraph 0018). Tsai teaches that incorporation of these ligands into iridium complexes improved sublimation of the resulting iridium complexes, color spectrum, of phosphorescence by the iridium complexes, and their EQE (external quantum efficiency) (paragraph 0018).
Tsai gives examples of such ancillary ligands on pages 7-10, one of which, L131, is pictured below.
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This ancillary ligand meets the requirements of the first embodiment of LB of the instant claim when all X groups are carbon atoms, Ra and Rc represent no substitution, and Rb is alkyl.
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 ancillary ligand of Tsai as the ancillary ligand in the compound of Ise in order to obtain improved sublimation of the resulting iridium complexes, color spectrum, phosphorescence by the iridium complexes, and their EQE, as taught by Tsai.
With respect to claim 16, Ise and Tsai teach the OLED of claim 15, and Ise teaches that the organic layer is the emissive layer, as discussed above, and the compound is a phosphorescent (paragraph 0184) dopant for use in the light-emitting layer (0185).
With respect to claim 19, Ise discloses a consumer product (an illumination light source, paragraph 0239), comprising an anode, a cathode, and an organic layer between the electrodes comprising a light emitting layer (paragraph 0179), and the light emitting layer comprises Compound TM-20 (page 32), which is pictured below
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The phenylpyridine ligand of compound TM-20 meets the requirements of condition 3 of instant Formula I when A is a 6-membered aromatic (benzene) ring, R represents an aryl (phenyl) group, Z1 is CR1, R1 is an alkyl (methyl) group, Z2 is CR2, Z3 is CR3, R3 is aryl (phenyl) group, Z4 is CR4, and Z5 is CR5, all other R characters are hydrogen atoms, and the ligand is coordinated to iridium.
Compound TM-20 is derived from Ise Formula (T-1), which is pictured below.
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In this formula, X-Y is any ancillary ligand (paragraph 0013, line 32).
However, while Ise teaches that the compound may comprise an ancillary ligand, Ise does not teach nor fairly suggest one of the instant LB ligands.
In analogous art, Tsai teaches novel ancillary ligands for metal complexes (paragraph 0018). Tsai teaches that incorporation of these ligands into iridium complexes improved sublimation of the resulting iridium complexes, color spectrum, of phosphorescence by the iridium complexes, and their EQE (external quantum efficiency) (paragraph 0018).
Tsai gives examples of such ancillary ligands on pages 7-10, one of which, L131, is pictured below.
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This ancillary ligand meets the requirements of the first embodiment of LB of the instant claim when all X groups are carbon atoms, Ra and Rc represent no substitution, and Rb is alkyl.
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 ancillary ligand of Tsai as the ancillary ligand in the compound of Ise in order to obtain improved sublimation of the resulting iridium complexes, color spectrum, phosphorescence by the iridium complexes, and their EQE, as taught by Tsai.
With respect to claim 20, Ise and Tsai teach the consumer product of claim 19, and Ise teaches the inventive devices are useful as illumination light sources (paragraph 0239), as discussed above.
With respect to claim 21, Ise and Tsai teach the compound of claim 1, and the ancillary ligand of Tsai meets the requirements of the instant claim when all X characters are carbon atoms, Ra and Rc represent no substitution and Rb is alkyl, as discussed above.
With respect to claim 25, Ise and Tsai teach the compound of claim 1, and the compound has the formula of Ir(LA)2(LB), as discussed above.
Claims 1, 3, 6, 13-16, and 19-22 are rejected under 35 U.S.C. 103 as being unpatentable over Nishizeki et al. (JP 2016/219490 A, using the attached translation for references).
With respect to claim 1, Nishizeki discloses Compound A-11 (paragraph 0111), which is pictured below.
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This compound is derived from Nishizeki general formula (1) (paragraph 0056), which is pictured below.
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Nishizeki also teaches that n is 2, m is 1, and L is a monoanionic bidentate ligand (paragraph 0070) such as the formula pictured below (paragraph 0097).
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In this formula, X is nitrogen (paragraph 0017), R’ is a substituent such as aryl (phenyl, paragraph 0099, line 14) and R” is hydrogen (paragraph 0099, line 1).
The phenylpyridine ligand of compound A-11 meets the requirements of condition 1 of instant Formula I when A is a 6-membered aromatic (benzene) ring, two R are joined to form a fused ring, Z1 is nitrogen, Z2 is CR2, Z3 is CR3, Z4 is CR4, and Z5 is CR5, R5 is a cycloalkyl (cyclohexyl) group, all other R characters are hydrogen atoms, and the ligand is coordinated to iridium. The ancillary ligand, L, meets the requirements of instant LB when LB is represented by the first embodiment of the claim when all X characters are carbon atoms and all R characters are hydrogen atoms.
Nishizeki includes each element claimed, with the only difference between the claimed invention and Nishizeki 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 from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic EL element, has higher external extraction quantum efficiency and less initial luminance deterioration, resulting in a longer life both at room temperature and at high temperatures (paragraph 0285) commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 3, Nishizeki teaches the compound of claim 1 and Z1 is nitrogen, Z5 is CR5, and R5 is cycloalkyl, as pictured above.
With respect to claim 6, Nishizeki teaches the compound of claim 1, and ring A is benzene, as discussed above.
With respect to claim 13, Nishizeki teaches the compound of claim 1, and LB is the instant eleventh embodiment of the claim when all R groups are hydrogen atoms, which is pictured below.
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With respect to claim 14, Nishizeki teaches the compound of claim 1, as discussed above.
Nishizeki also teaches that L may be represented by the bidentate ligand pictured below, wherein X is nitrogen (paragraph 0017), R’ is a substituent such as aryl (phenyl, paragraph 0099, line 14) and R” is hydrogen (paragraph 0099, line 1).
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This meets the requirements of the instant claim when all X groups are carbon atoms and all R groups are hydrogen atoms.
Nishizeki includes each element claimed, with the only difference between the claimed invention and Nishizeki 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 from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic EL element, has higher external extraction quantum efficiency and less initial luminance deterioration, resulting in a longer life both at room temperature and at high temperatures (paragraph 0285) commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 15, Nishizeki teaches an organic light emitting device comprising an anode, a cathode, and an organic layer between the electrodes and the organic layer comprises a compound of general formula 1 (paragraph 0030) such as Compound A-11 (paragraph 0111), which is pictured below.
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This compound is derived from Nishizeki general formula (1) (paragraph 0056), which is pictured below.
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Nishizeki also teaches that n is 2, m is 1, and L is a monoanionic bidentate ligand (paragraph 0070) such as the formula pictured below (paragraph 0097).
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In this formula, X is nitrogen (paragraph 0017), R’ is a substituent such as aryl (phenyl, paragraph 0099, line 14) and R” is hydrogen (paragraph 0099, line 1).
The phenylpyridine ligand of compound A-11 meets the requirements of condition 1 of instant Formula I when A is a 6-membered aromatic (benzene) ring, two R are joined to form a fused ring, Z1 is nitrogen, Z2 is CR2, Z3 is CR3, Z4 is CR4, and Z5 is CR5, R5 is a cycloalkyl (cyclohexyl) group, all other R characters are hydrogen atoms, and the ligand is coordinated to iridium. The ancillary ligand, L, meets the requirements of instant LB when LB is represented by the first embodiment of the claim when all X characters are carbon atoms and all R characters are hydrogen atoms.
Nishizeki includes each element claimed, with the only difference between the claimed invention and Nishizeki 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 from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic EL element, has higher external extraction quantum efficiency and less initial luminance deterioration, resulting in a longer life both at room temperature and at high temperatures (paragraph 0285) commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 16, Nishizeki teaches the OLED of claim 15, and Nishizeki teaches that the compound of general formula (1) is a phosphorescent dopant (paragraph 0048).
With respect to claim 19, Nishizeki teaches a consumer product (a television, paragraph 0234 line 3) comprising an organic light emitting device comprising an anode, a cathode, and an organic layer between the electrodes and the organic layer comprises a compound of general formula 1 (paragraph 0030) such as Compound A-11 (paragraph 0111), which is pictured below.
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This compound is derived from Nishizeki general formula (1) (paragraph 0056), which is pictured below.
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Nishizeki also teaches that n is 2, m is 1, and L is a monoanionic bidentate ligand (paragraph 0070) such as the formula pictured below (paragraph 0097).
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In this formula, X is nitrogen (paragraph 0017), R’ is a substituent such as aryl (phenyl, paragraph 0099, line 14) and R” is hydrogen (paragraph 0099, line 1).
The phenylpyridine ligand of compound A-11 meets the requirements of condition 1 of instant Formula I when A is a 6-membered aromatic (benzene) ring, two R are joined to form a fused ring, Z1 is nitrogen, Z2 is CR2, Z3 is CR3, Z4 is CR4, and Z5 is CR5, R5 is a cycloalkyl (cyclohexyl) group, all other R characters are hydrogen atoms, and the ligand is coordinated to iridium. The ancillary ligand, L, meets the requirements of instant LB when LB is represented by the first embodiment of the claim when all X characters are carbon atoms and all R characters are hydrogen atoms.
Nishizeki includes each element claimed, with the only difference between the claimed invention and Nishizeki 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 from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic EL element, has higher external extraction quantum efficiency and less initial luminance deterioration, resulting in a longer life both at room temperature and at high temperatures (paragraph 0285) commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 20, Nishizeki teaches the consumer product of claim 19 and Nishizeki teaches that the consumer product is a television, as discussed above.
With respect to claim 21, Nishizeki teaches the compound of claim 1, and Nishizeki also teaches that LB has the claimed structure when all X characters are carbon atoms and all R characters are hydrogen atoms, as pictured above.
With respect to claim 22, Nishizeki teaches the compound of claim 1, and Z1 is nitrogen and R5 is a cyclohexyl group, as discussed above.
Claims 1, 4, 6, 10, 13, 15-16, 19-20 and 23 are rejected under 35 U.S.C. 103 as being unpatentable over Cho et al. (WO 2015/056993 A1) in view of Hamada et al. (JP 2003/073665 A, using the previously provided translation for references).
With respect to claim 1, Cho teaches a compound of formula IrL1L2L3 (paragraph 13) wherein L1 and L2 are represented by partial formula A-2, and L3 is represented by partial formula A-4 (paragraph 15), which are pictured below.
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In formula A-2, R3 is a C5 cycloalkyl group and R4 is hydrogen (paragraph 17), and X is an oxygen atom (paragraph 16). In formula A-4, R7 and R8 are hydrogen atoms (paragraph 17).
Such a compound meets the requirements of condition (2) of instant Formula I when A is a 6-membered aromatic (benzene) ring, two R are joined to form a fused ring (dibenzofuran), Z1 is CR1 and R1 is cycloalkyl (cyclopentyl), Z2 is CR2, Z3 is CR3, Z4 is CR4, and Z5 is CR5, all other R characters are hydrogen atoms, and the ligand is coordinated to iridium. The ancillary ligand, L, meets the requirements of instant LB when LB is represented by the fifth embodiment of the claim (phenylpyridine) when all X characters are carbon atoms and all R characters are hydrogen atoms.
However, while Cho teaches R1 may be a cycloalkyl group and demonstrates instances where an R group is a C5 cycloalkyl group (See embodiment D-25 on page 6, and D-72 on page 7), Cho does not teach nor fairly suggest that the cycloalkyl group should be present at a location analogous to instant R1.
Hamada teaches an analogous EL material that is a phenylpyridine ligand that exhibits high luminance and high light-emitting efficiency (paragraph 0004).
Hamada gives a general formula by which to form the inventive compounds according to general formula (I), which is given below.
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Hamada teaches that by introducing a substituent, R, such as an alkyl group (paragraph 0009), the light emission voltage can be lowered and the light emission efficiency can be increased (paragraph 0010, lines 1-2).
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 introduce an alkyl group on the pyridine moiety at a position analogous to instant R1 in order to lower the emission voltage and increase the light emission efficiency, as taught by Hamada.
With respect to claim 4, Cho and Hamada teach the compound of claim 1, and Z5 is CH and Z1 is CR1 and R1 is cycloalkyl, as discussed above.
With respect to claim 6, Cho and Hamada teach the compound of claim 1 and ring A is benzene, as discussed above.
With respect to claim 10, Cho and Hamada teach the compound of claim 1, as discussed above.
Cho also teaches that L1 may be selected as A-2 and L2 and L3 may be A-4 (paragraph 14).
Such a modification produces a compound wherein the compound has the formula Ir(LA)(LB)2.
Cho includes each element claimed, with the only difference between the claimed invention and Cho 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 possible number of each ligand to arrive at the compound of the instant claim since the combination of ligands would have yielded the predictable result of an organometallic compound which, when used in an electroluminescent device, results in excellent luminous efficiency, power efficiency, color purity, low driving voltage, and good lifespan (abstract), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 13, Cho and Hamada teach the compound of claim 1, and LB is a phenylpyridine ligand, which is the embodiment below when all R groups are hydrogen atoms.
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With respect to claim 15, Cho discloses an organic light emitting device comprising an anode, a cathode, and an organic layer between the electrodes (paragraph 3) comprising a compound (paragraph 12) of formula IrL1L2L3 (paragraph 13) wherein L1 and L2 are represented by partial formula A-2, and L3 is represented by partial formula A-4 (paragraph 15), which are pictured below.
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In formula A-2, R3 is a C5 cycloalkyl group and R4 is hydrogen (paragraph 17), and X is an oxygen atom (paragraph 16). In formula A-4, R7 and R8 are hydrogen atoms (paragraph 17).
Such a compound meets the requirements of condition (2) of instant Formula I when A is a 6-membered aromatic (benzene) ring, two R are joined to form a fused ring (dibenzofuran), Z1 is CR1 and R1 is cycloalkyl (cyclopentyl), Z2 is CR2, Z3 is CR3, Z4 is CR4, and Z5 is CR5, all other R characters are hydrogen atoms, and the ligand is coordinated to iridium. The ancillary ligand, L, meets the requirements of instant LB when LB is represented by the fifth embodiment of the claim (phenylpyridine) when all X characters are carbon atoms and all R characters are hydrogen atoms.
However, while Cho teaches R1 may be a cycloalkyl group and demonstrates instances where an R group is a C5 cycloalkyl group (See embodiment D-25 on page 6, and D-72 on page 7), Cho does not teach nor fairly suggest that the cycloalkyl group should be present at a location analogous to instant R1.
Hamada teaches an analogous EL material that is a phenylpyridine ligand that exhibits high luminance and high light-emitting efficiency (paragraph 0004).
Hamada gives a general formula by which to form the inventive compounds according to general formula (I), which is given below.
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Hamada teaches that by introducing a substituent, R, such as an alkyl group (paragraph 0009), the light emission voltage can be lowered and the light emission efficiency can be increased (paragraph 0010, lines 1-2).
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 introduce an alkyl group on the pyridine moiety at a position analogous to instant R1 in order to lower the emission voltage and increase the light emission efficiency, as taught by Hamada.
With respect to claim 16, Cho and Hamada teach the OLED of claim 15, and Cho teaches the organic layer is an emissive layer and the compound is a dopant (paragraphs 10 and 12).
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 an emissive layer, as taught by Cho.
With respect to claim 19, Cho discloses an organic light emitting device comprising an anode, a cathode, and an organic layer between the electrodes (paragraph 3) comprising a compound (paragraph 12) of formula IrL1L2L3 (paragraph 13) wherein L1 and L2 are represented by partial formula A-2, and L3 is represented by partial formula A-4 (paragraph 15), which are pictured below.
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In formula A-2, R3 is a C5 cycloalkyl group and R4 is hydrogen (paragraph 17), and X is an oxygen atom (paragraph 16). In formula A-4, R7 and R8 are hydrogen atoms (paragraph 17).
Such a compound meets the requirements of condition (2) of instant Formula I when A is a 6-membered aromatic (benzene) ring, two R are joined to form a fused ring (dibenzofuran), Z1 is CR1 and R1 is cycloalkyl (cyclopentyl), Z2 is CR2, Z3 is CR3, Z4 is CR4, and Z5 is CR5, all other R characters are hydrogen atoms, and the ligand is coordinated to iridium. The ancillary ligand, L, meets the requirements of instant LB when LB is represented by the fifth embodiment of the claim (phenylpyridine) when all X characters are carbon atoms and all R characters are hydrogen atoms.
However, while Cho teaches R1 may be a cycloalkyl group and demonstrates instances where an R group is a C5 cycloalkyl group (See embodiment D-25 on page 6, and D-72 on page 7), Cho does not teach nor fairly suggest that the cycloalkyl group should be present at a location analogous to instant R1.
Hamada teaches an analogous EL material that is a phenylpyridine ligand that exhibits high luminance and high light-emitting efficiency (paragraph 0004).
Hamada gives a general formula by which to form the inventive compounds according to general formula (I), which is given below.
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Hamada teaches that by introducing a substituent, R, such as an alkyl group (paragraph 0009), the light emission voltage can be lowered and the light emission efficiency can be increased (paragraph 0010, lines 1-2).
Hamada also teaches that OLED devices may be incorporated into consumer products such as display elements (paragraph 0002)
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 introduce an alkyl group at a position analogous to instant R1 in order to lower the emission voltage and increase the light emission efficiency, as taught by Hamada. It also would have been obvious to use the OLED of Cho in a consumer product, such as a display element, as taught by Hamada.
With respect to claim 20, Cho and Hamada teach the consumer product of claim 19, and Hamada teaches that the consumer product includes a computer monitor (“a notebook computer display”, paragraph 0002).
With respect to claim 23, Cho and Hamada teach the compound of claim 1, and Z5 is CH, Z1 is CR1 and R1 is a cycloalkyl group, as discussed above.
Claims 4 and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Kita et al. (JP 2003/109758 A, using the attached translation for references), in view of Tsai et al. (US 2015/0129840 A1) as applied above, and further in view of Ikemizu et al. (US 2007/0196690 A1).
With respect to claim 4, Kita and Tsai teach the compound of claim 1, as discussed above.
Kita also teaches compound 26, which is pictured below.
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Compound 26, pictured and discussed above is derived from Kita general formula (6), which is pictured below.
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Kita teaches that R71 and R75 represent hydrogen or a substituent and the sum of the steric parameters of R71 and R75 is -0.6 or less (Es), and that by introducing a group with a small Es value into either or both of R71 and R75, the ring planes of the phenyl and pyridine skeletons are twisted (paragraph 0067), and that when the twist angle of the two rings is 9 degrees or more or less than 90 degrees, it forms a material that exhibits phosphorescence emission in the blue chromaticity region and when used as a dopant in an organic electroluminescent device, exhibits highly efficient emission in the blue region (paragraph 0037).
However, neither Kita nor Tsai teach that R75, which is a position analogous to instant R1 is an alkyl-substituted aryl.
In analogous art, Ikemizu teaches organometallic complexes which have a substituent with a steric parameter (Es) of -0.5 or less (abstract).
Ikemizu expands upon the work of Kita by teaching additional substituents which have a compatible steric parameter and could be reasonably expected to introduce a twist angle between 9 degrees and 90 degrees, as required by Kita.
Ikemizu teaches substituents such as 1-methyl phenyl (page 3), which would meet the requirements of the instant claim.
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 substituent of Ik