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 .
Priority
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in parent Application No. KR10-2022-0068505, filed on 06/03/2022.
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 07/19/2023, 11/29/2023, and 03/21/2025 were filed after the mailing date of the instant application on 06/02/2023. The submissions are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
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 1-5 and 7-20 are rejected under 35 U.S.C. 103 as being unpatentable over Layek et al. (US 2024/0324439 A1) in view of Lee et al. (US 2016/0268521 A1).
With respect to claims 1-4, 7, and 12, Layek discloses the organometallic compound below (page 82).
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The phenylpyridine ligand, LB, is derived from the formula below (paragraph 0093).
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Layek also teaches that Ra’ represents monosubstitution of a substituent (paragraph 0093) such as a silyl group (paragraph 0061, line 4).
However, Layek does not fairly suggest selection of a silyl group.
In analogous art, Lee teaches an organometallic compound comprising at least one phenylpyridine ligand with a silyl group (-Si(R4)(R5)(R6)) bonded to the fifth position of the pyridine ring (abstract and Formula 2B).
Lee teaches that a silyl group in the fifth position of the pyridine ring results in a compound with excellent heat resistance and decomposition resistance characteristics, and a device comprising the compound will have high stability during manufacturing, preserving, and/or driving and long lifespan (paragraph 0303). Also, inclusion of an organic layer comprising the compound in an organic light-emitting device gives a device with low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color purity (paragraph 0312).
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 modify the phenylpyridine ligand in the compound of Layek to comprise the TMS silyl group of Lee at the fifth position of the pyridine ring in order to obtain an organic light-emitting device gives a device with low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, and excellent color purity, as taught by Lee.
Such a modification produces a compound that meets the requirements of instant Formula 1 when M1 is iridium, L1 is represented by Formula 1A, L2 is represented by Formula 1B, n1 is 2 and n2 is 1. In Formula 1A, CY1 is a pyridine ring and X1 is a nitrogen atom, CY2 is a benzene ring and X2 is a carbon atom, b1 and b2 are 4 and R1 and R2 are hydrogen atoms, a1 is 1 and Z1 is Si(Q1)(Q2)(Q3) wherein Q1, Q2, and Q3 are all a C1 alkyl (methyl) group, and a2 is 0 so that Z2 is not present. In Formula 1B, X3 is a nitrogen atom, X4 is a carbon atom, Y1 and Y2 are both an oxygen atom, b31 is 2, b32 is 4, and b41 is 2 and R31, R32, and R41 are hydrogen atoms, b42 is 1 and R42 is a C1 alkyl (methyl) group.
With respect to claim 5, Layek and Lee teach the compound of claim 1, and the pyridine moiety of CY1 is represented by instant Formula 1-9, as pictured above.
With respect to claim 8, Layek and Lee teach the compound of claim 1, and the moiety is represented by instant Formula 3-1, for the reasons discussed above.
With respect to claim 9, Layek and Lee teach the compound of claim 1, and the moiety is represented by instant Formula 4-4 when R47 is a methyl group, as discussed above.
With respect to claims 10 and 11, Layek and Lee teach the compound of claim 1, and R1, R2, R31, R32, and R41 are hydrogen atoms, R42 is a C1 alkyl (methyl) group, and R51 to R53 and R61 to R63 are not present, as pictured and discussed above.
With respect to claims 13, Layek and Lee teach the compound of claim 1, and the compound is represented by instant Formula 5-2, as pictured above.
With respect to claim 14, Layek and Lee teach the compound of claim 1, and the compound is identical to instant Compound 20.
With respect to claims 15-17 and 19, Layek and Lee teach the compound of claim 1, and Layek also teaches an organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer between the anode and cathode (paragraph 0126), and the organic layer comprises a hole transport layer (HTL), an emissive layer (EML), and an electron transport layer (ETL), and the emissive layer comprises the compound as an emissive dopant (paragraph 0112) and is used in combination with a host material which is present in a greater amount (Table 1, EML, Host:Emitter 12%, page 151).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound in the emissive layer of an organic light emitting device with the claimed structure, as taught by Layek.
With respect to claim 18, Layek and Lee teach the device of claim 16, as discussed above.
Examiner is interpreting the compound of Layek and Lee to meet the requirements of the instant claim through its use as a preferred embodiment of the claimed invention, as given in compound 20 on page 44 of the instant specification. Products of identical chemical composition cannot have mutually exclusive properties, and it has been held that when the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present (See MPEP 2112.01(II)), and the compound of Layek and Lee reads on the claims.
Layek and Lee are silent to the maximum emission wavelength of the compound. However, this is considered to be a property of the composition. Support for this presumption comes from the use of like materials and like processes when the organometallic compound of Layek and Lee is used as an emissive dopant in the organic layer of an electroluminescent device, which would result in the claimed property described in the instant claims. Therefore, the claims are considered to be obvious over Layek and Lee, and the burden shifts to applicant to show that there is an unobvious difference between the claimed composition and the composition in the prior art. See MPEP 2112 (V). In addition, the presently claimed properties are considered to be present once the work of Layek and Lee were first provided. See MPEP 2112.01 (II).
With respect to claim 20, Layek and Lee teach the device of claim 15, and Layek also teaches that OLED devices may be used in an apparatus such as a flat panel display (paragraph 0004).
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 device in an electronic apparatus such as a flat panel display, as taught by Layek.
Claims 1-4, 6-13, 15-17, and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Layek et al. (US 2024/0324439 A1) in view of Choi et al. (US 2016/0268519 A1).
With respect to claims 1-4, 7, and 12, Layek discloses the organometallic compound below (page 82).
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The phenylpyridine ligand, LB, is derived from the formula below (paragraph 0093).
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136
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Layek also teaches that Rb’ represents monosubstitution of a substituent (paragraph 0093) such as a silyl group (paragraph 0061, line 4).
However, Layek does not fairly suggest selection of a silyl group.
In analogous art, Choi teaches an organometallic compound comprising at least one phenylpyridine ligand with a silyl group (abstract, Formula 2A, and Formula 2C).
Choi teaches that the organometallic if the description comprises at least one ligand of Formula 2A, which is a N-C bidentate ligand, giving the compound excellent thermal stability (paragraph 0240). Additionally, because the ligand of Formula 2A comprises at least one silyl group of Formula 2C, the compound has high T1 energy level (paragraph 0241).
Examiner notes that Choi uses TMS for the silyl group in the vast majority of example compounds (paragraph 0239).
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 modify the phenylpyridine ligand in the compound of Layek to comprise the TMS silyl group of Choi in order to obtain an compound with excellent thermal stability and a high T1 energy level, as taught by Choi.
Such a modification produces a compound that meets the requirements of instant Formula 1 when M1 is iridium, L1 is represented by Formula 1A, L2 is represented by Formula 1B, n1 is 2 and n2 is 1. In Formula 1A, CY1 is a pyridine ring and X1 is a nitrogen atom, CY2 is a benzene ring and X2 is a carbon atom, b1 and b2 are 4 and R1 and R2 are hydrogen atoms, a2 is 1 and Z2 is Si(Q1)(Q2)(Q3) wherein Q1, Q2, and Q3 are all a C1 alkyl (methyl) group, and a1 is 0 so that Z1 is not present. In Formula 1B, X3 is a nitrogen atom, X4 is a carbon atom, Y1 and Y2 are both an oxygen atom, b31 is 2, b32 is 4, and b41 is 2 and R31, R32, and R41 are hydrogen atoms, b42 is 1 and R42 is a C1 alkyl (methyl) group.
With respect to claim 6, Layek and Choi teach the compound of claim 1, and the benzene moiety of CY2 is represented by instant Formula 2-17, as discussed above.
With respect to claim 8, Layek and Choi teach the compound of claim 1, and the moiety is represented by instant Formula 3-1, for the reasons discussed above.
With respect to claim 9, Layek and Choi teach the compound of claim 1, and the moiety is represented by instant Formula 4-4 when R47 is a methyl group, as discussed above.
With respect to claims 10 and 11, Layek and Choi teach the compound of claim 1, and R1, R2, R31, R32, and R41 are hydrogen atoms, R42 is a C1 alkyl (methyl) group, and R51 to R53 and R61 to R63 are not present, as pictured and discussed above.
With respect to claims 13, Layek and Choi teach the compound of claim 1, and the compound is represented by instant Formula 5-7, as discussed above.
With respect to claims 15-17 and 19, Layek and Choi teach the compound of claim 1, and Layek also teaches an organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer between the anode and cathode (paragraph 0126), and the organic layer comprises a hole transport layer (HTL), an emissive layer (EML), and an electron transport layer (ETL), and the emissive layer comprises the compound as an emissive dopant (paragraph 0112) and is used in combination with a host material which is present in a greater amount (Table 1, EML, Host:Emitter 12%, page 151).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound in the emissive layer of an organic light emitting device with the claimed structure, as taught by Layek.
With respect to claim 20, Layek and Choi teach the device of claim 15, and Layek also teaches that OLED devices may be used in an apparatus such as a flat panel display (paragraph 0004).
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 device in an electronic apparatus such as a flat panel display, as taught by Layek.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Hwang et al. (US 2020/0287144 A1) – teaches compounds with germyl substituents.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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/RACHEL SIMBANA/Primary Examiner, Art Unit 1786
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