Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
Claims 17,19-20, 22,24 and 26-35 of P. Stoessel, US17/628,661 (01/20/2022) are pending, under examination on merits and are rejected.
Election/Restrictions
Pursuant to the restriction requirement, Applicant elected Group I (now claims 17,19-20, 22,24 and 26-35), with traverse, in the reply filed on 11/18/2024. Applicant amended claims by cancelling of claim 18 and incorporation of the claim 18 into claim 17 in the reply filed on 11/18/2024. In view of the claims amendment, the unity of invention is existed for the claim set submitted on 11/18/2024, therefore, the Requirement for Restriction/Election mailed on 09/17/2024 is withdrawn. Applicant added new claims 33-34, canceled claims 21, 25 in the reply filed on 03/11/2025. Applicant canceled claim 23 and combined it with claim 17 in the reply on 07/24/2025. Applicant added new claim 35 in the reply filed on 01/14/2026.
Claim Interpretation
During examination, a claim must be given its broadest reasonable interpretation consistent with the specification as it would be interpreted by one of ordinary skill in the art. MPEP § 2173.01(I); § 2111.01.
Interpretation of the Claim Terms “a bidentate cyclometalated ligand” and “bis(bidentate) cyclometalated subligand”
Independent claim 17 recites the following bolded claim terms, which require interpretation:
17. A process for preparing a cyclometalated iridium complex by reacting an iridium compound with one or more ligands that coordinate to the iridium under cyclometallation, . . .
L is the same or different at each instance and is a bidentate cyclometalated ligand in formula (2) or a bidentate cyclometalated subligand in formulae (1) and (3);
. . .
L" is a bis(bidentate) cyclometalated subligand that coordinates to both iridium atoms; V is the same or different at each instance and is a bridging unit which, in formula (1), joins the subligands L and L' to one another to form a tripodal
. . .
The specification defines “cyclometalated ligand” as:
In the context of the present invention, a cyclometalated ligand is a ligand which forms a metallacycle with the metal to which it coordinates, with at least one metal-carbon bond being present between the ligand and the metal.
Specification at page 3, line 19-21.
The specification defines “bidentate subligand” as:
The expression "bidentate subligand" in the context of this application means that L and L' would each be a bidentate ligand if the bridge V were absent. However, as a result of the formal abstraction of a hydrogen atom from this bidentate ligand and the attachment to the bridge V, it is no longer a separate ligand but a portion of the hexadentate ligand which thus arises, and so the term "subligand" is used therefor.
Specification at page 7, lines 1-7. The claim 17 bolded terms are interpreted consistently with the specification.
The specification defines the claim 17 term “carboxylic acid” as “an organic compound that bears one or more carboxyl groups (-COOH)”, which is consistent with the conventional meaning. See specification at page 54, lines 1-5.
Interpretation of the Claim Terms “iridium compound”
Claim 1 recites “iridium compound” in the following context:
Claim 1 . . . A process for preparing a cyclometalated iridium complex by reacting an iridium compound with one or more ligands that coordinate to the iridium under cyclometalation, wherein the process is conducted in anhydrous medium in the presence of at least one carboxylic acid; wherein the cyclometalated iridium complex has a structure of the formula (1), (2) or (3) . . .
The specification does not provide definition for “iridium compound”. See specification at page 51, lines 26-35 (teaching preferred iridium compounds). The claim 1 term “iridium compound” is broadly and reasonably interpreted as any compound comprising iridium.
Interpretation of the Claim Term “iridium carboxylate”
Claim 27 recites “iridium carboxylate”. The specification does not provide definition for “iridium carboxylate”; and the closest information disclosed by the specification as follow:
Iridium carboxylates of the formula (36) too, for example iridium acetate, are not a perfectly stoichiometric or defined compound, and useful compounds include various iridium carboxylates that may contain varying amounts of acetic acid, water and hydroxide, for example the compounds CAS [37598-27-9], [126310-98-3] or [52705-52-9]. The term "iridium carboxylate" in the context of the present invention includes all these compounds, regardless of their exact composition.
Specification at page 53, line 1-8 (emphasis added). The claim term of “iridium carboxylates” is broadly and reasonably in consistent with the specification interpreted as any compound comprising a coordination formed between iridium and a carboxylic group.
Summary of the Claimed Invention
The claims directed to a process for preparing a cyclometalated iridium complex of the formula of (1), (2) or (3) by reacting an iridium compound with one or more ligands that coordinate to the iridium under cyclometallation.
The specification provides a clear definition of the claim 17 term “ligand”, below, which is imported into claim 17:
The ligand used in the process of the invention, for complexes of the formula (1), corresponds to the compound of the formula (4).
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The ligands used in the process of the invention, for complexes of the formula (2), correspond to L and L', where the ligand L has a carbon-hydrogen bond rather than the carbon-iridium bond and the ligand L' has a hydrogen atom rather than a bond to the iridium.
The ligand used in the process of the invention, for complexes of the formula (3), corresponds to the compound of the formula (5).
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Specification at page 5, line 26 to page 6, line 22.
Thus, independent claim 17 is schematically summarized by Examiner as follows:
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The specification teaches several working examples with various ligands (i.e., L1-L16), four carboxylic acids (acetic, pivalic, benzoic, phenylacetic), and two iridium compounds (i.e., IrCl3 and Ir(OAc)3) Specification at pages 67-72.
The first working example (which is representative) is summarized by the Examiner below, where the claim 17 term correspondence is indicated and where glacial acetic acid corresponds to the required “at least one carboxylic acid of claim 1:
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Specification at pages 67-68.
Withdrawal Claim Rejections-35 USC § 103
Rejection of claims 17,19-20, 22,24 and 26-34 are rejected under 35 U.S.C. 103 as being unpatentable over P. Stoessel, et al, WO2018019688A1(published on 02-01-2018) (“Stoessel-WO”) in view of Y. Ji, CN 107383105 A (2017)(“Ji”) is withdrawn in view of the instant claim 17 has been amended with a new limitation that is:
“provided that R" does not comprise a bicyclic group”1
which cannot be met by the arts cited for the rejection made in the previous Office action, therefore, the rejection is withdrawn.
New 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 non-obviousness.
35 USC § 103 Rejection over Ji and Kwong
Claims of 17,19-20, 22,24 and 26-31, 33, 35 are rejected under 35 U.S.C. 103 as being unpatentable over a combination of Y. Ji, CN 107383105 A (2017)(“Ji”) and R. Kwong, et al., US 20130015430A1 (2013)(“Kwong).
Y. Ji, CN 107383105 A (2017)(“Ji”)
Note: Ji is published in Chinese, a copy of machine translation is attached as the second part of the reference, which results the total page of the full reference is 60, the format for the citation is xx/60.
Ji teaches one method of preparation of iridium complex (I-1) as follows:
IrCl3•3H2O (100 mg, 0.28 mmol) and 2-(5-trifluoromethyl-1H-pyrazol-3- yl)-6-phenylpyridine (164 mg, 0.57 mmol) and sodium acetate (465 mg, 5.67 mmol ) was dissolved in acetic acid (20 mL) at room temperature and reacted at 110°C for 24 hours. After the reaction was completed, the temperature was lowered back to room temperature, the acetic acid was evacuated under vacuum, washed with water and ethyl acetate three times, and purified by column chromatography (ethyl acetate : Hexane = 1: 4) gave the product after purification in 78% yield.
Ji at 29/60 and 51/60, Example 1, preparation of compound (I-1), emphasis added.
The Ji method can be schematically summarized as follows:
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Therefore, Ji fairly teaches one ordinary skilled artisan that acetic acid can be used as a solvent to form an iridium complex by reacting of Ir (III) salt such as IrCl3 with a free ligand comprising
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in the presence of NaOAc to form coordination binds between Ir(III) and ligand at a mild reaction condition as follows:
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Difference between Ji and the instant Claims 17,19-20, 22,24 and 26-31, 34-35
Ji differs from the claim 17 in that the ligand [2-(5-trifluoromethyl-1H-pyrazol-3- yl)-6-phenylpyridine] used by Ji does not meet the structural requirement of the claimed L, L’, L’’.
R. Kwong, et al., US 20130015430A1 (2013)(“Kwong)
Kwong teaches an organic electronic devices comprising a covalently bonded organic/inorganic composite layer. Kwong at abstract.
Kwong teaches working examples of his organic electronic devices such as devices 1-4, each of these devices comprises Green Dopant -1. Kwong at page 8, [0062], emphasis added.
Kwong teaches that the Green Dopant -1 is a mixture of compound A, B, C and D; and the compound B has a chemical structure as indicated below. Kwong at page 9, left col. Compound B and right col. note under BL2.
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The Kwong compound B maps the formula (2) in the instant claim 17 as:
L is
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L’ is
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which maps the formula L-39 as:
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Difference between Kwong and the instant Claims 17,19-20, 22,24 and 26-31, 34-35
Kwong does not teach a method to synthesize the Kwong compound B .
Obviousness Rationales of the Claims 17,19-20, 22,24 and 26-31, 34-35
It would have been prima facie obvious for one skilled artisan to arrive at the instantly claimed invention based on the teachings from Kwong and Ji with a reasonable expectation of success before the effective filing date of the claimed invention.
Claim 17 is obvious because one ordinary skill seeking the Kwong compound B as a green dopant material for an organic electronic devices is motivated to use method taught by Ji to synthesize the Kwong compound B as indicated below, thus arrive at a method meeting each and every limitation of claim 17, therefore claim 17 is obvious.
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One of ordinary skilled artisan has a motivation to do so with a reasonable expectation of success because:
(i). Kwong teaches the compound can be used as a green dopant material while does not teach how to prepare of it;
(ii). Ji teaches that acetic acid can be used as a solvent to form an iridium complex by reacting of IrCl3 with a free ligand comprising
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in the presence of NaOAc to form coordination binds between Ir(III) and the
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; the complexation can be completed at a mild condition with a good yield.
Claim 19 is obvious because the Kwong compound B meets the structure limitation of the formula (2a) as discussed above.
Claim 20 is obvious because in the Kwong compound B, the ligands or subligands coordinate to the iridium via one carbon atom and one nitrogen atom.
Claim 22 is obvious because the L and L’ in the Kwong compound B meets the limitation of L-2-1 as discussed above.
Claims 24 and 26 are obvious because neither claim 24 nor claim 16 can further limit the structure of formula (2) in claim 17.
Claim 27 is obvious because the iridium compound in the proposed method is iridium(III) chloride.
Claim 28-29 are obvious because the acid in the above proposed method is acetic acid.
Claim 30 is obvious because the above proposed method does not use a hydrate.
Claim 31 is obvious because NaOAc is added in the proposed method.
Claim 33 is obvious because Ji teaches to use 20.98 g of acetic acid (20 ml× 1.049g/ml) for 0.28 mmol of iridium compound, which is 75 g acetic acid per mmol of iridium compound.
Claim 35 is obvious because Kwong compound B does not comprise a bicyclic group.
35 USC § 103 Rejection over Ji and Tsai
Claims of 17,19-20, 22,24 and 27-33, 35 are rejected under 35 U.S.C. 103 as being unpatentable over an combination of Y. Ji, CN 107383105 A (2017)(“Ji”) and J-Y. Tsai, et al, US 20180026208A1 (Published on 01/25/2018); claim 34 is rejected as applied above for the rejection of claim 17 further in view of P. Stoessel, et al, WO2018019688A1(published on 02-01-2018) (“Stoessel-WO”).
Y. Ji, CN 107383105 A (2017)(“Ji”)
Ji has been discussed as above.
J-Y. Tsai, et al, US 20180026208A1 (Published on 01/25/2018)
Tsai teaches a compound having Formula I:
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Tsai at page 6, [0059].
Tsai teaches examples of compound Formula I such as the compound has a structure as indicated below:
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Tsai at page 12, right col. the first compound.
The Tsai compound maps the formula (1) in the instant claim 17 as:
V is
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;
L’ is
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L is
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, which maps the L-39 in claim 17 as indicated below
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Tsai teaches that the compound formula I can be used as an emissive dopant because the compound can produce emission via phosphorescence, fluorescence, thermally activated delayed fluorescence.
Tsai does not teach how to synthesize of the compound of
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, Tsai teaches a method to synthesis another species of
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by reacting of
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with [IrCl(COD)]2 without detail guidance on the reaction conditions and product yield.
Obviousness Rationales of Claims 17,19-20, 22,24 and 27-31, 33-35
It would have been prima facie obvious for one skilled artisan to arrive at the instantly claimed invention based on the teachings from Tsai and Ji with a reasonable expectation of success before the effective filing date of the claimed invention.
Claims 17 and 34 are obvious because one of ordinary skilled seeking the Tsai compound as an emissive dopant is motivated to prepare the compound by reacting of Ir(III) salt sch as IrCl3 with a free ligand in acetic acid in the presence of NaOAc as below, thus arrive at a method meeting each and every limitation of claims 17 and 34, therefore, claims 17 and 34 are obvious.
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One of ordinary skilled artisan has a motivation to do so with a reasonable expectation of success because:
(i).Tsai teaches the compound can be used as a dopant while does not teach a detailed method for preparation of it;
(ii). Ji teaches that acetic acid can be used as a solvent to form an iridium complex by reacting of IrCl3 with a free ligand comprising
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in the presence of NaOAc to form coordination binds between Ir(III) and the
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; the complexation can be completed at a mild condition with a good yield.
Claim 19 is obvious because the Tsai compound meets the structure limitation of the formula (1a) as discussed above.
Claim 20 is obvious because in the Tsai compound, the ligands or subligands coordinate to the iridium via one carbon atom and one nitrogen atom.
Claim 22 is obvious because the L and L’ in the Tsai compound meets the limitation of L-1-1 as discussed above.
Claims 24 is obvious because claim 24 cannot further limit the structure of formula (1) in claim 17.
Claim 27 is obvious because the iridium compound in the proposed method is iridium(III) chloride.
Claim 28-29 are obvious because the acid in the above proposed method is acetic acid.
Claim 30 is obvious because the above proposed method does not use a hydrate, further when IrCl3•3H2O is used one ordinary skilled artisan is motivated to add acetic anhydride so that can react the water to for acetic acid to make the reaction condition to be anhydrous.
Claim 31 is obvious because NaOAc is added in the proposed method.
Claim 33 is obvious because Ji teaches to use 20.98 g of acetic acid (20 ml× 1.049g/ml) for 0.28 mmol of iridium compound, which is 75 g acetic acid per mmol of iridium compound.
Claim 35 is obvious because the Tsai compound does not comprise a bicyclic group.
Obviousness Rationales of Claim 32
As mentioned above that the combination of Ji and Tsai teaches a method meeting each and every limitation of claim 17.
The method taught by Ji and Tsai differs 32 only in that Ji and Tsai do not teach to include a chiral carboxylic acid into the reaction mixture.
As mentioned in the previous Office action that Stoessel-WO also teaches iridium complex and enantiomerically pure or enantiomerically enriching synthesis of iridium complex is possible by complexation in a chiral medium. Stoessel-US at page 40, [0205], line 1-2 and page 42,[0211], line 1-3.
Claim 32 is obvious because the Tsai compound is a chiral compound, one ordinary skill seeking enantiomerically pure or enantiomerically enriching synthesis is motivated to further modify the proposed method by adding a chiral acid as Stoessel-WO teaches that an enantiomerically pure or enantiomerically enriching synthesis is possible by complexation in a chiral medium.
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.
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 As applicant mentioned in the remarks filed on 01/14/2026 that the specification discloses that R” can be a cyclic alkyl group ( See Specification at page 32, line 17). The specification also discloses that a cyclic alkyl groups including a bicyclic group (See Specification at page 11, line 32). Therefore, the negative limitation in the instant claim 17 has a basis in the original application. MPEP 2173.05(i).