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 .
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 11/07/2022, 11/07/2022, and 10/22/2025 were filed after the mailing date of the instant application on 11/07/2022. The submissions are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Abstract
The abstract of the disclosure is objected to because it does not appear to contain a technical disclosure of the invention to which it pertains.
Specifically, the abstract indicates that the application is drawn to transition metal compounds having a 1,2,3-triazine, which is not the case as evidenced by the instant claims and disclosure which do not require a 1,2,3-triazine nor describe a compound having a 1,2,3-triazine moiety.
Applicant is reminded of the proper content of an abstract of the disclosure.
In chemical patent abstracts for compounds or compositions, the general nature of the compound or composition should be given as well as its use, e.g., “The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics.” Exemplification of a species could be illustrative of members of the class. For processes, the type of reaction, reagents and process conditions should be stated, generally illustrated by a single example unless variations are necessary.
A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-20 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for K1 and K2 and L1 is a single bond, does not reasonably provide enablement for all the given definitions of K1, K2, and L1. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the invention commensurate in scope with these claims.
With respect to independent claims 1, 17, and 20, the claims require a compound comprising ligand LA of Formula I, pictured below.
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In this formula, K1 and K2 may be independently selected from a direct bond, oxygen and sulfur atom, and L1 may be selected from a single bond, S, C=R’, CR’R”, SiR’R”, GeR’R”, BR’, BR’R”, and NR’. However, the claim requires that the ligand LA complexes to a metal M through the dashed lines to form a 5-membered chelate ring. These limitations are not in agreement with each other because K1, K2, and L1 must be a single bond for a 5-membered chelate to form. Introduction of a divalent group at K1, K2, and L1 creates anything from a 6-membered to 8-membered chelate.
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As such, a compound wherein K1, K2, and L1 are anything other than a single bond but still form the required 5-membered chelate ring is not enabled by the application, as originally filed. The factors set forth in In re Wands, 858 F.2d 731, 737 (Fed. Cir. 1988) are discussed below.
(A) The breadth of the claims
The present claims are directed to a compound comprising ligand LA of Formula I, pictured below.
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In this formula, K1 and K2 may be independently selected from a direct bond, oxygen and sulfur, and L1 may be selected from a single bond, S, C=R’, CR’R”, SiR’R”, GeR’R”, BR’, BR’R”, and NR’.
However, these options can form anywhere from a 5-membered to an 8-membered chelate ring. It is unclear how to arrive at the required 5-membered chelate ring without eliminating another required claim aspect such as the X characters that belong to rings A1 and A2. Additionally, there is no guidance given on compounds which have anything other than a single bond at these locations in the instant specification.
(B) The nature of the invention
The invention relates to an organometallic compound with at least one, condensed, saturated heterocycle, where the heteroatom in the heterocycle is chosen from silicon or germanium. Compounds with a metal-heteroatom bond (such as instant K1 and K2) and compounds with a divalent linker between a biaryl ring system (such as instant L1) were known prior to the effective filing date. Compounds which form a 6-8-membered chelate are enabled and known.
However, allowing for K1 and K2 to be independently selected from oxygen and sulfur, and for L1 to be selected from S, C=R’, CR’R”, SiR’R”, GeR’R”, BR’, BR’R”, and NR’, while still requiring a 5-membered chelate is nonsense. Unless applicant is redefining what a 5-membered chelate is (See MPEP 2173.05(a)), a 5-membered chelate cannot be required while the claims allow for a 6-8-membered chelate or vice versa.
(C) The state of the prior art
As discussed above, the invention relates to an organometallic compound with at least one, condensed, saturated heterocycle, where the heteroatom in the heterocycle is chosen from silicon or germanium. As outlined in the rejections below, compounds which meet the requirements of the instant claims were known prior to the effective filing date of the claimed invention. What isn’t known is a biaryl ligand comprising one or more divalent linking groups and which still qualifies as a 5-membered chelate.
(D) The level of one of ordinary skill
As discussed above, compounds with a metal-heteroatom bond (such as instant K1 and K2) and compounds with a divalent linker between aromatic moieties (such as instant L1) were known prior to the effective filing date. Compounds which form a 6-8-membered chelate are enabled and known. Further, one having ordinary skill in the art would know how to synthesize such a compound. However, a person having ordinary skill in the art would not call a 6, 7, or 8-membered chelate a 5-membered chelate. A person having ordinary skill in the art would use the correct terminology.
(E) The level of predictability in the art
The level of predictability presented by Applicant is very low. As outlined above, when K1 and K2 are individually or both a single bond or divalent linking group and L1 is a single bond or divalent group, these options can form anywhere from a 5-membered to an 8-membered chelate ring. When K1, K2, and L1 are anything other than a single bond, it is unclear how to arrive at the required 5-membered chelate ring without eliminating another required claim aspect such as the X characters that belong to rings A1 and A2. Not every optional limitation of the claim can be used to arrive at the required limitation of a 5-membered chelate.
(F) The amount of direction provided by the inventor
There is no direction provided by the inventor on how to form a 6-8-membered chelate ring. Every single example compound is a 5-membered chelate. Unless applicant is redefining what a 5-membered chelate is (See MPEP 2173.05(a)), a 5-membered chelate cannot be required while the claims allow for a 6-8-membered chelate or vice versa. Absent a statement along the lines of, “5-membered chelate is meant to encompass 6-8 membered chelate rings” the limitations of K1, K2, and L1 being selected as anything other than a direct bond and the compound forming a 5-membered chelate directly contradict one another.
(G) The existence of working examples
Applicant’s specification includes 0 working examples of devices or compounds wherein K1, K2, and L1 are anything other than a direct bond and form a 5-membered chelate.
(H) The quantity of experimentation needed to make or use the invention based on the content of the disclosure
As discussed above, compounds with a metal-heteroatom bond (such as instant K1 and K2) and compounds with a divalent linker between aromatic moieties (such as instant L1) were known prior to the effective filing date. Compounds which form a 6-8-membered chelate are enabled and known. Further, one having ordinary skill in the art would know how to synthesize such a compound. However, a person having ordinary skill in the art would not call a 6, 7, or 8-membered chelate a 5-membered chelate. A person having ordinary skill in the art would use the correct terminology. The amount of experimentation needed to arrive at a 5-membered chelate which is 6-8 membered is high because a person having ordinary skill in the art would not call a 6, 7, or 8-membered chelate a 5-membered chelate.
As such, claims 1, 17, and 20 contain subject matter which was not described in the specification in such a way as to enable one skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention.
Claims 2-16, and 18-19 are rejected by virtue of dependency
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 11 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 11, the claim contains embodiments of ligand LA which are all outside the scope of parent claim 2 because they do not comprise a structure of Formula II. Instead, many of the structures appear to be ancillary ligands that meet the requirements of previously described ligand Ly. However, the list of ligands given in claim 11 also comprises an acetylacetonate derivative which cannot meet the requirements of LA or Ly, so it is unclear what Applicant is claiming, what the instant structures are describing, and how they fit into the claimed invention.
In continuing examination, this claim will be interpreted as dependent from claim 4, wherein the structures are embodiments of ligand Ly, except that the acetylacetonate derivative will not be examined as it does not appear to fit into the claimed invention in any aspect.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 4-6, 11, and 16 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
With respect to claim 11, the claim contains embodiments of ligand LA which are all outside the scope of parent claim 2 because they do not comprise a structure of Formula II.
With respect to claims 4-6 and 16, the claims contain compounds wherein Z1-Z4 are selected as something other than CRR’, SiRR’, and GeRR’. There are several compounds wherein at least one of Z1-Z4 comprises an sp2 carbon atom, which is outside the scope of parent claim 2.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1 and 12-15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hwang et al. (US 2016/0155963 A1).
With respect to claim 1, Hwang teaches Compound 166 (page 68), which is pictured below.
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This compound meets the requirements of instant Formula I when A1 is a monocyclic ring system comprising a 6-membered heterocyclic ring (pyridine), A2 is a monocyclic ring system comprising a 6-membered carbocyclic ring (benzene), X1 is a nitrogen atom, and X2-X4 are carbon atoms, K1 and K2 are a direct bond, L1 is a single bond, RA forms the moiety Formula II, and RB represents zero substitution.
In Formula II, n is 0 and Z1 is not present, Z2 is SiRR’, and Z3-Z4 are each CRR’. In Z2, R and R’ are each alkyl (methyl) groups, and in Z3 and Z4, R and R’ are both hydrogen atoms.
With respect to claim 12, Hwang teaches the compound of claim 1, and the ligand LA is selected as ligand LA347-4 wherein RE is represented by R2 and G is represented by G18.
With respect to claim 13, Hwang teaches the compound of claim 1, and the compound has the formula Ir(LA)2(LB) wherein x is 2, y is 1, and z is 0 so that LC is not present and 3 is the oxidation state of iridium.
With respect to claim 14, Hwang teaches the compound of claim 13, and LB is a phenylpyridine ligand, which is the sixth embodiment of the instant claim when all Y characters are carbon atoms, as pictured above.
With respect to claim 15, Hwang teaches the compound of claim 12, and LB is represented by instant LB1, as pictured above.
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 following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 2-11 and 17-20 are rejected under 35 U.S.C. 103 as being unpatentable over Hwang et al. (US 2016/0155963 A1) as applied above, and further in view of Stoessel et al. (US 2007/0082284 A1).
With respect to claim 2, Hwang teaches the compound of claim 1, as discussed above.
Hwang also teaches that the ligand can be coordinated to a platinum core, wherein the sum of n1 and n2 is 2 (paragraph 0055).
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 metal nucleus from the finite list of possible metal cores to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when included in an organic light-emitting device, results in low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (paragraph 0230), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Hwang does not teach nor fairly suggest bridging the ligands with an oxygen atom to form a tetradentate ligand of instant Formula III.
In analogous art, Stoessel teaches organometallic compounds for use in an organic light emitting device (abstract and title) comprising a bridging unit “V” (paragraph 0020 and Structure 1). Stoessel teaches that the purpose of the bridge V is to promote the formation of mononuclear metal complexes of structure 1 (tetradentate organometallic complex), and suppress or completely prevent the formation of coordination polymers on reaction of the ligand of structure 2 (tetradentate chelating ligand) with metal compounds (paragraph 0021).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use an oxygen linking group in the tetradentate platinum ligand of Hwang in order to promote the formation of mononuclear metal complexes and suppress or completely prevent the formation of coordination polymers of the chelating ligand with metal compounds, as taught by Stoessel.
Such a modification produces a compound that meets the requirements of instant Formula III when M1 is platinum, Z1* is a nitrogen atom and Z2* is a carbon atom, K3 and K4 are a direct bond, L2 is an oxygen atom, L3 is a direct bond, and L4 is an absent bond, RE and RF represent no substitution, and all other characters are as defined above.
With respect to claim 3, Hwang and Stoessel teach the compound of claim 2, and the compound has the structure of the instant first embodiment, for the reasons pictured and stated above.
With respect to claims 4 and 5, Hwang and Stoessel teach the compound of claim 2, and the compound is selected as having the structure below for ligand LA’ when each X variable is a carbon atom, ZA is a silicon atom, REE is a methyl group (Me, R3) and all other R groups are hydrogen atoms (R1), and the second structure below for the ligand Ly when RF and RE represent no substitution, as discussed above.
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With respect to claim 6, Hwang and Stoessel teach the compound of claim 4, and the compound is selected as instant LA4-(R3)(R1)(R1)(R1).
With respect to claim 7, Hwang and Stoessel teach the compound of claim 2, and RA forms the moiety Formula II, and RB represents zero substitution, in Z2, R and R’ are each alkyl (methyl) groups, and in Z3 and Z4, R and R’ are both hydrogen atoms, as discussed above.
With respect to claim 8, Hwang and Stoessel teach the compound of claim 2 and A1 is pyridine and A2 is benzene, as discussed above.
With respect to claim 9, Hwang and Stoessel teach the compound of claim 2 and one of Z1-Z4 is SiRR’ and the remainder of Z1-Z4 are CRR’, as discussed above.
With respect to claim 10, Hwang and Stoessel teach the compound of claim 2 and in Z2 each of R and R’ are an alkyl group.
Compound 166, pictured and discussed above is derived from Hwang formula 2(27) (page 12), which is pictured below.
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Hwang also teaches that R21 is a methyl group (paragraph 0127, line 2) and b11 is 4 (paragraph 0119).
Such a modification produces a compound wherein every R and R’ in CRR’ is alkyl.
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 metal nucleus from the finite list of possible metal cores to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when included in an organic light-emitting device, results in low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (paragraph 0230), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 11, Hwang and Stoessel teach the compound of claim 4, and the ligand Ly is a phenylpyridine ligand, which is the sixth embodiment of the claim when all Y characters are carbon atoms, as pictured above.
With respect to claim 17, Hwang teaches an organic light emitting device (OLED) comprising an anode (paragraph 0239), a cathode (paragraph 0310), and an organic layer between the electrodes (paragraph 0241) and the organic layer comprises a compound of formula 1 (paragraph 0229), such as Compound 166 (page 68), which is pictured below.
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Hwang also teaches that the ligand can be coordinated to a platinum core, wherein the sum of n1 and n2 is 2 (paragraph 0055).
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 metal nucleus from the finite list of possible metal cores to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when included in an organic light-emitting device, results in low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (paragraph 0230), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Hwang does not teach nor fairly suggest bridging the ligands with an oxygen atom to form a tetradentate ligand of the instant claim.
In analogous art, Stoessel teaches organometallic compounds for use in an organic light emitting device (abstract and title) comprising a bridging unit “V” (paragraph 0020 and Structure 1). Stoessel teaches that the purpose of the bridge V is to promote the formation of mononuclear metal complexes of structure 1 (tetradentate organometallic complex), and suppress or completely prevent the formation of coordination polymers on reaction of the ligand of structure 2 (tetradentate chelating ligand) with metal compounds (paragraph 0021).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use an oxygen linking group in the tetradentate platinum ligand of Hwang in order to promote the formation of mononuclear metal complexes and suppress or completely prevent the formation of coordination polymers of the chelating ligand with metal compounds, as taught by Stoessel.
Such a modification produces a compound that meets the requirements of the instant formula when A1 is a monocyclic ring system comprising a 6-membered heterocyclic ring (pyridine), A2 is a monocyclic ring system comprising a 6-membered carbocyclic ring (benzene), moiety E is a monocyclic 6-membered carbocyclic (benzene) ring, moiety F is a monocyclic 6-membered heterocyclic (pyridine) ring, X1 is a nitrogen atom, and X2-X4 are carbon atoms, Z1* is a carbon atom and Z2* is a nitrogen atom, K1-K4 are a direct bond, L1 and L3 are a single bond, L2 is an oxygen atom and L4 is an absent bond, RA forms the moiety Formula II, and RD, RE and RF represent zero substitution, n is 0 and Z1 is not present, Z2 is SiRR’, and Z3-Z4 are each CRR’. In Z2, R and R’ are each alkyl (methyl) groups, and in Z3 and Z4, R and R’ are both hydrogen atoms, and M is Pt.
With respect to claim 18, Hwang and Stoessel teach the OLED of claim 17, and Hwang also teaches that the organic layer may further comprise a host (paragraph 0274), such as mCP (page 90), which comprises a carbazole moiety, which is pictured below.
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With respect to claim 19, Hwang and Stoessel teach the OLED of claim 17, and Hwang teaches that the organic layer further comprises a host (paragraph 0274), and the host may be compound H1 (page 91), which is pictured below, which is a compound of the instant claim.
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With respect to claim 20, Hwang teaches a full-color organic light-emitting device (a consumer device, paragraph 0293), comprising an organic light emitting device (OLED) comprising an anode (paragraph 0239), a cathode (paragraph 0310), and an organic layer between the electrodes (paragraph 0241) and the organic layer comprises a compound of formula 1 (paragraph 0229), such as Compound 166 (page 68), which is pictured below.
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Hwang also teaches that the ligand can be coordinated to a platinum core, wherein the sum of n1 and n2 is 2 (paragraph 0055).
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 metal nucleus from the finite list of possible metal cores to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when included in an organic light-emitting device, results in low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (paragraph 0230), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Hwang does not teach nor fairly suggest bridging the ligands with an oxygen atom to form a tetradentate ligand of the instant claim.
In analogous art, Stoessel teaches organometallic compounds for use in an organic light emitting device (abstract and title) comprising a bridging unit “V” (paragraph 0020 and Structure 1). Stoessel teaches that the purpose of the bridge V is to promote the formation of mononuclear metal complexes of structure 1 (tetradentate organometallic complex), and suppress or completely prevent the formation of coordination polymers on reaction of the ligand of structure 2 (tetradentate chelating ligand) with metal compounds (paragraph 0021).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use an oxygen linking group in the tetradentate platinum ligand of Hwang in order to promote the formation of mononuclear metal complexes and suppress or completely prevent the formation of coordination polymers of the chelating ligand with metal compounds, as taught by Stoessel.
Such a modification produces a compound that meets the requirements of the instant formula when A1 is a monocyclic ring system comprising a 6-membered heterocyclic ring (pyridine), A2 is a monocyclic ring system comprising a 6-membered carbocyclic ring (benzene), moiety E is a monocyclic 6-membered carbocyclic (benzene) ring, moiety F is a monocyclic 6-membered heterocyclic (pyridine) ring, X1 is a nitrogen atom, and X2-X4 are carbon atoms, Z1* is a carbon atom and Z2* is a nitrogen atom, K1-K4 are a direct bond, L1 and L3 are a single bond, L2 is an oxygen atom and L4 is an absent bond, RA forms the moiety Formula II, and RD, RE and RF represent zero substitution, n is 0 and Z1 is not present, Z2 is SiRR’, and Z3-Z4 are each CRR’. In Z2, R and R’ are each alkyl (methyl) groups, and in Z3 and Z4, R and R’ are both hydrogen atoms, and M is Pt.
Claims 1-14 and 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Okuda et al. (WO 2016/088354 A1) and further in view of Hwang et al. (US 2016/0155963 A1).
With respect to claim 1, Okuda discloses compound 13 (paragraph 0054), which is pictured below.
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This compound is derived from Okuda formula (8) (paragraph 0048), which is pictured below.
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Okuda also teaches that R1 is an alkyl group having 4 carbon atoms (paragraph 0050), such as t-butyl (paragraph 0025), R4 may be a silyl group (paragraph 0008, line 19), and that a plurality of R4 substituents may be bonded to each other to form a ring (paragraph 0032).
However, Okuda does not teach nor fairly suggest a moiety analogous to instant Formula II condensed to a ring of compound 13.
In analogous art, Hwang teaches organometallic compound comprising a silyl substituent on the pyridine ring of a phenylpyridine ligand for use in an organic light emitting device (abstract, title, and Formula 2, paragraph 0010).
Hwang teaches that the silyl group may form a condensed aliphatic ring, such as the one pictured in Formula 2(27) (page 12), which is pictured below.
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Hwang teaches that organic light-emitting device comprising compounds of the invention demonstrate low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (paragraph 0023).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use a condensed, 5-membered, saturated cycloalkyl comprising silylene in order to obtain an organic light-emitting device with low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color, as taught by Hwang.
Such a modification produces a compound that meets the requirements of the instant claim when A1 is a monocyclic ring system comprising a 6-membered heterocyclic ring (pyridine), A2 is a monocyclic ring system comprising a 6-membered carbocyclic ring (benzene), X1 is a nitrogen atom, and X2-X4 are carbon atoms, K1 and K2 are a direct bond, L1 is a single bond, RA forms the moiety Formula II, and RB represents zero substitution.
In Formula II, n is 0 and Z1 is not present, Z2 is SiRR’, and Z3-Z4 are each CRR’. In Z2, R and R’ are each alkyl (methyl) groups, and in Z3 and Z4, R and R’ are both hydrogen atoms.
With respect to claim 2, Okuda and Hwang teach the compound of claim 1, and the compound has the structure of instant Formula III when M1 is platinum, Z1* is a nitrogen atom and Z2* is a carbon atom, K3 and K4 are a direct bond, L2 is an oxygen atom, L3 is NR’ and R’ is an aryl group which is joined with RE to form a carbazole moiety, L4 is an absent bond, RF represent no substitution, and all other characters are as defined above.
With respect to claim 3, Okuda and Hwang teach the compound of claim 2, and the compound has the structure of the instant sixth embodiment, as pictured above.
With respect to claims 4 and 5, Okuda and Hwang teach the compound of claim 2, and the compound is selected as having the structure below for ligand LA when each X variable is a carbon atom, ZA is a silicon atom, REE is a methyl group (Me, R3) and all other R groups are hydrogen atoms (R1), and the second structure below for the ligand Ly when RF is a t-butyl group and RE represents no substitution, as discussed above.
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With respect to claim 6, Okuda and Hwang teach the compound of claim 4, and the compound is selected as instant LA4-(R3)(R1)(R1)(R1).
With respect to claim 7, Okuda and Hwang teach the compound of claim 2, and RA forms the moiety Formula II, and RD represents zero substitution, in Z2, R and R’ are each alkyl (methyl) groups, in Z3 and Z4, R and R’ are both hydrogen atoms, and in NR’, R’ is aryl as discussed above.
With respect to claim 8, Okuda and Hwang teach the compound of claim 2 and A1 is pyridine and A2 is benzene, as discussed above.
With respect to claim 9, Okuda and Hwang teach the compound of claim 2 and one of Z1-Z4 is SiRR’ and the remainder of Z1-Z4 are CRR’, as discussed above.
With respect to claim 10, Okuda and Hwang teach the compound of claim 2 and in Z2 each of R and R’ are an alkyl group, and in NR’, R’ is aryl as discussed above.
In Hwang formula 2(27) (page 12), Hwang also teaches that the cycloalkyl group comprising a silylene moiety may comprise substituent R21 described in the manner pictured below.
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Hwang also teaches that R21 is a methyl group (paragraph 0127, line 2) and b11 is 4 (paragraph 0119).
Such a modification produces a compound wherein in CRR’ every R and R’ is alkyl.
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 metal nucleus from the finite list of possible metal cores to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when included in an organic light-emitting device, results in low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (paragraph 0230), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 11, Okuda and Hwang teach the compound of claim 4, and the ligand Ly is represented by the embodiment below when all Y characters are carbon atoms, as pictured above.
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With respect to claim 12, Okuda and Hwang teach the compound of claim 1, and the ligand LA is represented by LA347-4 wherein RE is represented by R2 and G is represented by G18.
With respect to claim 13, Okuda and Hwang teach the compound of claim 1, and the compound has the formula Pt(LA)(LB) wherein x is 1, y is 1, and z is 0 so that LC is not present and 2 is the oxidation state of platinum.
With respect to claim 14, Okuda and Hwang teach the compound of claim 13, and the ligand LB is represented by the embodiment below when all Y characters are carbon atoms, as pictured above.
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With respect to claim 16, Okuda and Hwang teach the compound of claim 2, as discussed above.
In Hwang formula 2(27) (page 12), Hwang also teaches that the silylene moiety may be substituted at R1 and R2 by -CD3 (paragraphs 0143-0144).
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Such a modification produces the instant third compound.
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 metal nucleus from the finite list of possible metal cores to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when included in an organic light-emitting device, results in low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (paragraph 0230), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 17, Okuda teaches an organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer between the electrodes, and the organic layer comprises a compound of formula 1 (paragraph 0072), such as compound 13 (paragraph 0054), which is pictured below.
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This compound is derived from Okuda formula (8) (paragraph 0048), which is pictured below.
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Okuda also teaches that R1 is an alkyl group having 4 carbon atoms (paragraph 0050), such as t-butyl (paragraph 0025), R4 may be a silyl group (paragraph 0008, line 19), and that a plurality of R4 substituents may be bonded to each other to form a ring (paragraph 0032).
However, Okuda does not teach nor fairly suggest a moiety analogous to instant Formula II condensed to a ring of compound 13.
In analogous art, Hwang teaches organometallic compound comprising a silyl substituent on the pyridine ring of a phenylpyridine ligand for use in an organic light emitting device (abstract, title, and Formula 2, paragraph 0010).
Hwang teaches that the silyl group may form a condensed aliphatic ring, such as the one pictured in Formula 2(27) (page 12), which is pictured below.
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Hwang teaches that organic light-emitting device comprising compounds of the invention demonstrate low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (paragraph 023).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use a condensed, 5-membered, saturated cycloalkyl comprising silylene in order to obtain an organic light-emitting device with low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color, as taught by Hwang.
Such a modification produces a compound that meets the requirements of the instant formula when A1 is a monocyclic ring system comprising a 6-membered heterocyclic ring (pyridine), A2 is a monocyclic ring system comprising a 6-membered carbocyclic ring (benzene), moiety E is a monocyclic 6-membered carbocyclic (benzene) ring, moiety F is a monocyclic 6-membered heterocyclic (pyridine) ring, X1 is a nitrogen atom, and X2-X4 are carbon atoms, Z1* is a carbon atom and Z2* is a nitrogen atom, K1-K4 are a direct bond, L1 is a single bond, L2 is an oxygen atom, L3 is NR’ wherein R’ is an aryl group that together with RE forms a carbazole moiety, and L4 is an absent bond, RA forms the moiety Formula II, and RD and RE represent no substitution and RF is a t-butyl group, n is 0 and Z1 is not present, Z2 is SiRR’, and Z3-Z4 are each CRR’. In Z2, R and R’ are each alkyl (methyl) groups, in Z3 and Z4, R and R’ are both hydrogen atoms, and M1 is Pt.
With respect to claim 18, Okuda and Hwang teach the OLED of claim 17, and Hwang also teaches that the organic layer may further comprise a host (paragraph 0274), such as mCP (page 90), which comprises a carbazole moiety, which is pictured below.
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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 host material of Hwang, as taught by Hwang.
With respect to claim 19, Okuda and Hwang teach the OLED of claim 17, and Hwang teaches that the organic layer further comprises a host (paragraph 0274), and the host may be compound H1 (page 91), which is pictured below, which is a compound of the instant claim.
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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 host of Hwang, as taught by Hwang.
With respect to claim 20, Okuda teaches a flat panel display device (a consumer device, paragraph 0099), comprising an organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer between the electrodes, and the organic layer comprises a compound of formula 1 (paragraph 0072), such as compound 13 (paragraph 0054), which is pictured below.
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This compound is derived from Okuda formula (8) (paragraph 0048), which is pictured below.
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Okuda also teaches that R1 is an alkyl group having 4 carbon atoms (paragraph 0050), such as t-butyl (paragraph 0025), R4 may be a silyl group (paragraph 0008, line 19), and that a plurality of R4 substituents may be bonded to each other to form a ring (paragraph 0032).
However, Okuda does not teach nor fairly suggest a moiety analogous to instant Formula II condensed to a ring of compound 13.
In analogous art, Hwang teaches organometallic compound comprising a silyl substituent on the pyridine ring of a phenylpyridine ligand for use in an organic light emitting device (abstract, title, and Formula 2, paragraph 0010).
Hwang teaches that the silyl group may form a condensed aliphatic ring, such as the one pictured in Formula 2(27) (page 12), which is pictured below.
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Hwang teaches that organic light-emitting device comprising compounds of the invention demonstrate low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color (paragraph 023).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use a condensed, 5-membered, saturated cycloalkyl comprising silylene in order to obtain an organic light-emitting device with low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color, as taught by Hwang.
Such a modification produces a compound that meets the requirements of the instant formula when A1 is a monocyclic ring system comprising a 6-membered heterocyclic ring (pyridine), A2 is a monocyclic ring system comprising a 6-membered carbocyclic ring (benzene), moiety E is a monocyclic 6-membered carbocyclic (benzene) ring, moiety F is a monocyclic 6-membered heterocyclic (pyridine) ring, X1 is a nitrogen atom, and X2-X4 are carbon atoms, Z1* is a carbon atom and Z2* is a nitrogen atom, K1-K4 are a direct bond, L1 is a single bond, L2 is an oxygen atom, L3 is NR’ wherein R’ is an aryl group that together with RE forms a carbazole moiety, and L4 is an absent bond, RA forms the moiety Formula II, and RD and RE represent no substitution and RF is a t-butyl group, n is 0 and Z1 is not present, Z2 is SiRR’, and Z3-Z4 are each CRR’. In Z2, R and R’ are each alkyl (methyl) groups, in Z3 and Z4, R and R’ are both hydrogen atoms, and M1 is Pt.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Choi et al. (US 2016/0181530 A1) – teaches relevant germanium organometallics.
Li et al. (US 2002/0076576 A1) – teaches deuterating OLED materials.
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/RACHEL SIMBANA/Examiner, Art Unit 1786