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
Applicant's election without traverse of species (A1) a compound comprising a ligand LA of Formula I of claim 1, wherein M is Ir, and (B2) the ligand LA comprises a structure of Formula IV but not Formula III of claim 5, in the reply filed on 8/28/2025 is acknowledged.
In the Office Action of 10/01/2025, the requirement of species election has been updated to withdraw the requirement of election for (B1) and (B2) only. Applicant’s election without traverse is directed to the species (A1) a compound comprising a ligand LA of Formula I of claim 1, wherein M is Ir.
Claim 16 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group.
With respect to the instant claims 8 and 10-11, a search of the prior art did not show the elected species. As none of the claims were specifically drawn to applicant's elected species in combination with the limitations of claims 8 and 10-11 in independent form, no claims have been indicated as allowable. However, claim written in independent form which requires all the limitations of claims 8 and 10-11 as well as being limited to the elected species along with any dependent claims which require all the limitation of claims 8 and 10-11 as well as being limited to the elected species would be allowable.
Claims 8 and 10-11 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 as well as being limited to the elected species. This objection to the claims is only with respect to Applicant’s elected species.
It is noted that the potential allowability of claims 8 and 10-11 has not be determined with respect to species beyond Applicant's elected species, i.e. potential examinable species that could found once the search is expanded beyond Applicant's elected species.
Response to Amendment
The amendment of 01/01/2026 has been entered.
Disposition of claims:
Claims 1-20 are pending.
Claim 16 has been withdrawn.
Claims 1, 5, 8, 10, 15, 17, and 20 have been amended.
The amendment of claim 5 has overcome the rejection of claim 5 under 35 U.S.C. 112(b) set forth in the last Office Action. The rejection has been withdrawn.
The amendment of claim 10 has overcome the rejection of claim 10 under 35 U.S.C. 112(b) set forth in the last Office Action. The rejection has been withdrawn.
The amendments of claims 1, 5, 8, 10, 15, 17, and 20 have overcome:
the rejections of claims 1-7, 10, 12-14, 17-18, and 20 under 35 U.S.C. 103 as being unpatentable over Kwong et al. (US 2009/0108737 A1, hereafter Kwong) in view of Stoessel et al. (US 2015/0171348 A1),
the rejection of claim 19 under 35 U.S.C. 103 as being unpatentable over Kwong et al. (US 2009/0108737 A1) in view of Stoessel et al. (US 2015/0171348 A1) as applied to claims 1-7, 10, 12-14, 17-18, and 20 above, further in view of Kai et al. (US 2010/0187977 A1, hereafter Kai) set forth in the last Office Action.
The rejections have been withdrawn.
Response to Arguments
Applicant’s arguments see page 125-126 of the reply filed 01/01/2026 regarding the rejections of claims 1-9, 12-14, and 17-20 under 35 U.S.C. 103 as being unpatentable over Stoessel et al. (US 2015/0171348 A1, hereafter Stoessel), and the rejections of claims 15 and 20 under 35 U.S.C. 103 as being unpatentable over Stoessel et al. (US 2015/0171348 A1) as applied to the claims 1-9, 12-14, and 17-20 above, further in view of Boudreault et al. (US 2015/0001472 A1, hereafter Boudreault) set forth in the Office Action of 10/01/2025 have been considered.
Applicant argues that the amended claims distinguish over Stoessel, which requires a five-member structure (where n is 1).
While the amended claims overcome the rejections referring to the Modified compound of Stoessel (2) (see section 32 of the last Office Action), the amendment does not overcome the rejections referring to Modified compounds of Stoessel (1) and (3) (see sections 30 and 47).
First, the amendment does not overcome some of the compounds that the previous Office Action recited.
The cited rejections refer to the Modified compound of Stoessel (1) (see section 30 of the last Office Action).
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The left ligand of the Modified compound of Stoessel (1) still reads on the all the limitations of the ligand LA of the instant claims. In the left ligand, the pyridine ring directly coordinated to M (i.e. Ir) is a ring formed by joining two adjacent substituents RA which are each alkenyl and heteroalkenyl. The moiety A is not directly coordinated to M such that the proviso “with the proviso that if moiety A is directly coordinated to M, then n is 0, 2, or 3” is not applied.
The cited rejections also refer to the Modified compound of Stoessel (3) (see section 47 of the last Office Action).
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The left ligand of the Modified compound of Stoessel (3) still reads on the all the limitations of the ligand LA of the instant claims. In the left ligand, the benzene ring directly coordinated to M (i.e. Ir) is a ring formed by joining two adjacent substituents RA which are each alkyl and aryl. Thus, the moiety A is not directly coordinated to M such that the proviso “with the proviso that if moiety A is directly coordinated to M, then n is 0, 2, or 3” is not applied.
Secondly, Stoessel does not teach only 5-membered ring (i.e. n=1). Stoessel teaches Formula (4-8) ([0058]) which is a fluorine-substituted 6-membered ring.
Stoessel teaches Compound Ir555 ([0244], page 140).
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In the Compound Ir555, the cycloalkenyl ring enclosed by a dashed circle in the figure above does not contain fluorine, which does not read on the limitation of Formula I of the instant claims. However, Stoessel does teach that the compound of Stoessel can contain a cycloalkenyl ring of Formula (4), wherein A2 can be each C(R1)2; G can be an ethylene group substituted by R2; R1 can be hydrogen or fluorine; and R2 can be hydrogen ([0007]-[0020]). Stoessel exemplifies a fluorocyclohexenyl ring of Formula (4-8) ([0058]). Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound Ir555 Ir(L74)3 of Stoessel by substituting the cycloalkenyl ring with the fluorocyclohexenyl ring of Formula (4-8), as taught by Stoessel.
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The modification provides Modified compound of Stoessel (4). It is noted that the isoquinoline ring of the compound is the ring A of Applicant’s Formula I of the instant claims. In the compound, the 6-membered bicyclic ring reads on the cycloalkyl ring fused to the ring A of Applicant’s Formula I, wherein n=2. The 5-membered bicyclic ring reads on the limitations of the R’ of Applicant’s Formula I since two adjacent R’ groups can be joined to form a ring.
Additionally, Stoessel teaches Compound Ir(L28)3 ([0235], page 103).
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In the compound, the cycloalkenyl ring enclosed by a dashed circle in the figure is bound to the pyridine ring corresponding to the CyD of Formula (1); however, Stoessel does teach that CyD and/or CyC can contain two adjacent carbon atoms each substituted by radical R, wherein the R together with C can form a cycloalkenyl ring of Formula (4) ([0016]). Stoessel teaches that CyC can be represented by Formula (CyC-13), wherein X can be CR ([0033]). Stoessel exemplifies a fluorocyclohexenyl ring of Formula (4-8) ([0058]). Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound Ir(L28)3 of Stoessel by substituting any one of substitution positions 1-2, 2-3, or 3-4 with the fluorocyclohexenyl ring of Formula (4-8), as taught by Stoessel.
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The modification provides Modified compound of Stoessel (5), which reads on all the limitations of Applicant’s Formula I of the instant claims.
For at least this reason, the argument is not found to be persuasive. New grounds of rejections are applied. The amendment necessitates new grounds of rejections, making this Office Action final.
Applicant argues that the cited arts do not read on the claims and cited MPEP 2144.09 reciting “Isomers having the same empirical formula but different structures are not necessarily considered equivalent by chemists skilled in the art and therefore are not necessarily suggestive of each other. Applicant further recites Ex parte Mowry and In re Mills.
Respectfully, the Examiner does not agree.
The instant rejections refer to position isomer arguments as outlined below.
The Modified compound of Stoessel (1) as outlined above has similar structure as Applicant’s embodiment of claim 15 (the 5th compound on page 113, hereafter Compound p113-5).
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The first difference between two compounds is that the methyl groups of the acetylacetonate ancillary ligand (i.e. the part pointed by arrows in the figure above) are required to be substituted by diethyl groups. However, it would have been obvious to substitute the methyl groups each with a diethyl-substituted methyl group, based on the teaching of Boudreault.
Boudreault discloses a compound having an acetylacetonate ancillary ligand ([0015]).
Boudreault teaches that incorporation of the acetylacetonate ligand of Boudreault provides narrow emission spectrum, decreased evaporation temperature, and improved device efficiency ([0017]).
Boudreault exemplifies ligand LA1 which has identical structure as the ancillary ligand of Applicant’s Compound p113-5.
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Modified compound of Stoessel (1) by substituting the terminal methyl groups of the acetylacetone ligand (i.e. the methyl groups pointed by the arrows in the figure above) with each diethyl-substituted methyl group, as taught by Boudreault.
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The modification provides Compound of Stoessel as modified by Boudreault (1).
Compound of Stoessel as modified by Boudreault (1) differs from the Applicant’s Compound p113-5 in that the pentafluoro cycloalkenyl group is substituted to the positions 4-5 of the benzene ring of the isoquinoline group (i.e. see the annotated numbers in the figure above). However, Stoessel does teach the pentafluoro cycloalkenyl group corresponding to the Formula (3) of Stoessel can be bonded to any adjacent positions X of the isoquinoline ring represented by Formula CyD-2,
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([0039]-[0040]).
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Stoessel as modified by Boudreault (1) by substituting the substitution positions of the pentafluoro cycloalkenyl group from the positions 4-5 to the positions 5-6 of the isoquinoline ring, as taught by Stoessel.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the substitution positions of the pentafluoro cycloalkenyl group from the positions 4-5 to the positions 5-6 of the isoquinoline ring would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are only four substitution positions (i.e. positions 1-2, 3-4, 4-5, and 5-6) to substitute the pentafluoro cycloalkenyl of Formula (3) to the isoquinoline ring. The selection of the substitution positions 5-6 would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E). (emphasis added)
Furthermore, the compounds of Compound of Stoessel as modified by Boudreault (1) is a position isomer with similar compounds in which the pentafluoro cycloalkenyl group is substituted to the positions 5-6 of the isoquinoline ring.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Therefore, at the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to modify Compound of Stoessel as modified by Boudreault (1) shown above such that the pentafluoro cycloalkenyl group is substituted to the positions 5-6 of the isoquinoline ring. A compound in which the pentafluoro cycloalkenyl group is substituted to the positions 5-6 of the isoquinoline ring would represent a position isomer of the Compound of Stoessel as modified by Boudreault (1). One of ordinary skill in the art would expect that the position isomers having each respective structure would act in similar manner.
The modification provides Compound of Stoessel as modified by Boudreault (2) which has identical structure as Applicant’s Compound p113-5.
First, the rejections are not only relying on the position isomer argument but also relying on the other ground of rejection, MPEP 2143 (I)(E), which is not argued by Applicant.
There are only four substitution positions (i.e. positions 1-2, 3-4, 4-5, and 5-6) to substitute the pentafluoro cycloalkenyl of Formula (3) to the isoquinoline ring. The selection of the substitution positions 5-6 would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E). (emphasis added).
Secondly, Applicant fails to provide any evidence to prove that the Compound of Stoessel as modified by Boudreault (1) would not act in similar manner as the position isomer, Applicant’s Compound p113-5. The only difference between the two compounds is the substitution position of the fluoro cyclopentyl ring.
In response to Applicant’s arguments regarding the Ex parte Mowry, the cited case law is different from the instant application because cyclohexylstyrene is not a position isomer of isohexylstyrene. The former is directed to a cycloalkyl group while the latter is directed to a linear and branched alkyl group. In response to Applicant’s arguments regarding the homology argument, no homologous argument was applied, making this argument moot.
For at least this reason, the arguments are not persuasive.
Applicant’s arguments see page 127 of the reply filed 01/01/2026 regarding the rejections of claims 1-7, 10, 12-14, 17-18, and 20 under 35 U.S.C. 103 as being unpatentable over Kwong et al. (US 2009/0108737 A1, hereafter Kwong) in view of Stoessel et al. (US 2015/0171348 A1), and the rejection of claim 19 under 35 U.S.C. 103 as being unpatentable over Kwong et al. (US 2009/0108737 A1) in view of Stoessel et al. (US 2015/0171348 A1) as applied to claims 1-7, 10, 12-14, 17-18, and 20 above, further in view of Kai et al. (US 2010/0187977 A1, hereafter Kai) set forth in the Office Action of 10/01/2025 have been considered.
Applicant argues that the amended claims distinguish over the cited art.
The rejections refer to the Compound of Kwong as modified by Stoessel. The ligand of the compound does not read on the limitation of Applicant’s Formula 1 of the amended claims. Thus, the rejections are withdrawn.
Claim Objections
Claim 10 is objected to because of the following informalities:
In claim 10, some of formula structures have the same name while structural formulas are different. Examples includes LAi”-45 through LAi”-48.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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.
Regarding claim 14, Applicant recites formulas including at least Ir(LAi-m)3, Ir(LA1-1)3 to Ir(LA2508-73)3, Ir(LAi-m)2(LCj-I), Ir(LA1-1)2(LC1-I) to Ir(LA2508-73)2(LC1416-I), etc., wherein in the formulas the ligands LAi-m and LA1-1 to LA2508-73 are not defined either in claim 14 nor the claim 12 from which the claim 14 depend. It is unclear what is the limitation of the ligands LAi-m and LA1-1 to LA2508-73, rendering this claim indefinite.
For the purpose of the prosecution, the Examiner interprets the limitation to mean the limitation of each of the ligands LAi-m and LA1-1 to LA2508-73 is same as the limitation of the ligand LA of claim 1, since claim 14 is dependent from claim 1 via claim 12, wherein the limitation of the ligand LA of claim 12 is same as that of claim 1.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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 1-7, 9, 12-14, and 17-20 are rejected under 35 U.S.C. 103 as being unpatentable over Stoessel et al. (US 2015/0171348 A1, hereafter Stoessel).
Regarding claims 1-7, 9, and 12-14, Stoessel discloses a compound of Formula (1) and used for an organic light emitting device ([0001], [0007]), wherein the compound of Stoessel contains a cycloalkenyl ring represented by Formula (3) or (4) ([0016]). Stoessel exemplifies Compound Ir555 ([0244], page 140).
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In the Compound Ir555, the cycloalkenyl ring enclosed by a dashed circle in the figure above does not contain fluorine, which does not read on the limitation of Formula I of the instant claims. However, Stoessel does teach that the compound of Stoessel can contain a cycloalkenyl ring of Formula (3), wherein A1 and A3 can be each C(R3)2; A2 can be C(R1)2; R1 can be fluorine; and R3 can be fluorine ([0012], [0017]-[0020]). Stoessel exemplifies a hexafluoro cycloalkenyl ring of Formula (3-28) ([0057]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound Ir555 Ir(L74)3 of Stoessel by substituting the cycloalkenyl ring at the position corresponding to Formula (3) with the hexafluoro cycloalkenyl ring of Formula (3-28), as taught by Stoessel.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the cycloalkenyl ring at the position corresponding to the Formula (3) with the cycloalkenyl ring of Formula (3-28) in the compound of Stoessel would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Modified compound of Stoessel (1), meeting all the limitations of claims 1-4 and 12-14.
It is noted that the pyridine ring directly coordinated to M (i.e. Ir) in the compound is a ring formed by joining two adjacent substituents RA which are each alkenyl and heteroalkenyl. Thus, the moiety A is not directly coordinated to M such that the proviso “with the proviso that if moiety A is directly coordinated to M, then n is 0, 2, or 3” is not applied.
Stoessel discloses a compound of Formula (1) and used for an organic light emitting device ([0001], [0007]), wherein the compound of Stoessel contains a cycloalkenyl ring represented by Formula (3) or (4) ([0016]). Stoessel exemplifies Compound Ir(L28)3 ([0235], page 103).
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In the compound, the cycloalkenyl ring enclosed by a dashed circle in the figure is bound to the pyridine ring corresponding to the CyD of Formula (1); however, Stoessel does teach that CyD and/or CyC can contain two adjacent carbon atoms each substituted by radical R, wherein the R together with C can form a cycloalkenyl ring of Formula (3) ([0016]). Stoessel teaches that CyC can be represented by Formula (CyC-13), wherein X can be CR ([0033]). Stoessel exemplifies a hexafluoro cycloalkenyl ring of Formula (3-28) ([0057]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound Ir(L28)3 of Stoessel by substituting any one of substitution positions 1-2, 2-3, or 3-4 with the hexafluoro cycloalkenyl ring of Formula (3-28), as taught by Stoessel.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the substituent R groups from hydrogen to a hexafluoro cycloalkenyl ring at the position corresponding to the Formula (CyC-13) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Modified compound of Stoessel (3), meeting all the limitations of claims 1-4 and 12-14.
It is noted that the fluorocyclohexenyl ring can be positioned any one of edges 1-2, 2-3, or 3-4. The figure above is just one representation of three possible resultant compounds.
It is noted that the pyridine ring directly coordinated to M (i.e. Ir) in the compound is a ring formed by joining two adjacent substituents RA which are each alkyl and aryl. Thus, the moiety A is not directly coordinated to M such that the proviso “with the proviso that if moiety A is directly coordinated to M, then n is 0, 2, or 3” is not applied.
Stoessel discloses a compound of Formula (1) and used for an organic light emitting device ([0001], [0007]), wherein the compound of Stoessel contains a cycloalkenyl ring represented by Formula (3) or (4) ([0016]). Stoessel exemplifies Compound Ir555 ([0244], page 140).
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In the Compound Ir555, the cycloalkenyl ring enclosed by a dashed circle in the figure above does not contain fluorine, which does not read on the limitation of Formula I of the instant claims. However, Stoessel does teach that the compound of Stoessel can contain a cycloalkenyl ring of Formula (4), wherein A2 can be each C(R1)2; G can be an ethylene group substituted by R2; R1 can be hydrogen or fluorine; and R2 can be hydrogen ([0007]-[0020]). Stoessel exemplifies a fluorocyclohexenyl ring of Formula (4-8) ([0058]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound Ir555 Ir(L74)3 of Stoessel by substituting the cycloalkenyl ring with the fluorocyclohexenyl ring of Formula (4-8), as taught by Stoessel.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the cycloalkenyl ring at the position corresponding to the Formula (3) or (4) with the fluorocyclohexenyl ring of Formula (4-8) in the compound of Stoessel would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Modified compound of Stoessel (4), meeting all the limitations of claims 1-7 and 12-14.
It is noted that the isoquinoline ring of the compound is the ring A of Applicant’s Formula I of the instant claims. In the compound, the 6-membered bicyclic ring reads on the cycloalkyl ring fused to the ring A of Applicant’s Formula I, wherein n=2. The 5-membered bicyclic ring reads on the limitations of the R’ of Applicant’s Formula I since two adjacent R’ groups can be joined to form a ring.
Stoessel discloses a compound of Formula (1) and used for an organic light emitting device ([0001], [0007]), wherein the compound of Stoessel contains a cycloalkenyl ring represented by Formula (3) or (4) ([0016]). Stoessel exemplifies Compound Ir(L28)3 ([0235], page 103).
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In the compound, the cycloalkenyl ring enclosed by a dashed circle in the figure is bound to the pyridine ring corresponding to the CyD of Formula (1); however, Stoessel does teach that CyD and/or CyC can contain two adjacent carbon atoms each substituted by radical R, wherein the R together with C can form a cycloalkenyl ring of Formula (4) ([0016]). Stoessel teaches that CyC can be represented by Formula (CyC-13), wherein X can be CR ([0033]). Stoessel exemplifies a fluorocyclohexenyl ring of Formula (4-8) ([0058]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound Ir(L28)3 of Stoessel by substituting any one of substitution positions 1-2, 2-3, or 3-4 with the fluorocyclohexenyl ring of Formula (4-8), as taught by Stoessel.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the substituent R groups from hydrogen to a fluorocyclohexenyl ring at the position corresponding to the Formula (CyC-13) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Modified compound of Stoessel (5), meeting all the limitations of claims 1-6, 9, and 12-14.
It is noted that the fluorocyclohexenyl ring can be positioned any one of edges 1-2, 2-3, or 3-4. The figure above is just one representation of three possible resultant compounds. All of the three resultant compounds can read on all the limitations of the claim 9 regardless of the fusion position.
Regarding claims 17-20, the Modified compound of Stoessel (1), (3), (4), and (5) read on all the features of the Formula I of the claim 1 as outlined above.
Stoessel does not disclose a specific organic light emitting device comprising the Modified compound of Stoessel (1) (or (3), (4), or (5)); however, Stoessel does teach that the compound of Stoessel can be used for an organic light emitting device ([0097]).
Stoessel teaches the structure of an organic light emitting device comprising an anode, an emissive layer (Compound M7 as a host and the compound of Stoessel as an emitting dopant), and a cathode ([0279]-[0281], D-IrR1 in Table 1).
The compound M7,
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(page 169) has identical structure as the 4th compound of the instant claim 19.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Modified compound of Stoessel (1) (or (3), (4), or (5)) by incorporating it as the emitting dopant of an organic light emitting device, as taught by Stoessel.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the light emitting dopants would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified organic light emitting device of Stoessel (1) (or (3), (4), or (5)) comprising an anode, an emissive layer (Modified compound of Stoessel (1) (or (3), (4), or (5)) as an emitting dopant, Compound M7 of Stoessel as a host), and a cathode, meeting all the limitations of claims 17-19.
The Modified organic light emitting device of Stoessel (1), (3), (4), and (5) are each equated with a consumer product, meeting all the limitations of claim 20.
Claims 15 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Stoessel et al. (US 2015/0171348 A1) as applied to the claims 1-7, 9, 12-14, and 17-20 above, further in view of Boudreault et al. (US 2015/0001472 A1, hereafter Boudreault).
Regarding claim 15, the Modified compound of Stoessel (1) reads on all the features of claim 1 as outlined above.
The compound has similar structure as Applicant’s embodiment of claim 15 (the 5th compound on page 113, hereafter Compound p113-5).
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The first difference between two compounds is that the methyl groups of the acetylacetonate ancillary ligand (i.e. the part pointed by arrows in the figure above) are required to be substituted by diethyl groups. However, it would have been obvious to substitute the methyl groups each with a diethyl-substituted methyl group, based on the teaching of Boudreault.
Boudreault discloses a compound having an acetylacetonate ancillary ligand ([0015]).
Boudreault teaches that incorporation of the acetylacetonate ligand of Boudreault provides narrow emission spectrum, decreased evaporation temperature, and improved device efficiency ([0017]).
Boudreault exemplifies ligand LA1 which has identical structure as the ancillary ligand of Applicant’s Compound p113-5.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Modified compound of Stoessel (1) by substituting the terminal methyl groups of the acetylacetone ligand (i.e. the methyl groups pointed by the arrows in the figure above) with each diethyl-substituted methyl group, as taught by Boudreault.
The motivation of doing so would have been to provides narrow emission spectrum, decreased evaporation temperature, and improved device efficiency, based on the teaching of Boudreault.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A).
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The modification provides Compound of Stoessel as modified by Boudreault (1).
Compound of Stoessel as modified by Boudreault (1) differs from the Applicant’s Compound p113-5 in that the pentafluoro cycloalkenyl group is substituted to the positions 4-5 of the benzene ring of the isoquinoline group (i.e. see the annotated numbers in the figure above). However, Stoessel does teach the pentafluoro cycloalkenyl group corresponding to the Formula (3) of Stoessel can be bonded to any adjacent positions X of the isoquinoline ring represented by Formula CyD-2,
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([0039]-[0040]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Stoessel as modified by Boudreault (1) by substituting the substitution positions of the pentafluoro cycloalkenyl group from the positions 4-5 to the positions 5-6 of the isoquinoline ring, as taught by Stoessel.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the substitution positions of the pentafluoro cycloalkenyl group from the positions 4-5 to the positions 5-6 of the isoquinoline ring would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are only four substitution positions (i.e. positions 1-2, 3-4, 4-5, and 5-6) to substitute the pentafluoro cycloalkenyl of Formula (3) to the isoquinoline ring. The selection of the substitution positions 5-6 would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
Furthermore, the compounds of Compound of Stoessel as modified by Boudreault (1) is a position isomer with similar compounds in which the pentafluoro cycloalkenyl group is substituted to the positions 5-6 of the isoquinoline ring.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Therefore, at the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to modify Compound of Stoessel as modified by Boudreault (1) shown above such that the pentafluoro cycloalkenyl group is substituted to the positions 5-6 of the isoquinoline ring. A compound in which the pentafluoro cycloalkenyl group is substituted to the positions 5-6 of the isoquinoline ring would represent a position isomer of the Compound of Stoessel as modified by Boudreault (1). One of ordinary skill in the art would expect that the position isomers having each respective structure would act in similar manner.
The modification provides Compound of Stoessel as modified by Boudreault (2) which has identical structure as Applicant’s Compound p113-5.
Regarding claim 20, the Modified organic light emitting device of Stoessel (1), (3), (4), and (5) each reads on all the features of claim 17 as outlined above.
The device comprises an anode, an emissive layer (Modified compound of Stoessel (1) (or (3), (4), or (5)) as an emitting dopant, Compound M7 of Stoessel as a host), and a cathode.
Stoessel does not disclose a specific flat panel display device comprising the Modified organic light emitting device of Stoessel; however, Stoessel does teach that the compound of Stoessel can be used for display applications ([0119]).
Boudreault teaches that the organic light emitting device can be incorporated in a flat panel display device ([0031]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Modified organic light emitting device of Stoessel (1) (or (3), (4), or (5)) by incorporating it into a flat panel display device as taught by Stoessel.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of organic light emitting devices in a flat panel display device would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides a consumer product (i.e. flat panel display device) comprising the Modified organic light emitting device of Stoessel (1) (or (3), (4), or (5)).
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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/SEOKMIN JEON/Primary Examiner, Art Unit 1786