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 based on an application filed in Korea on 01/20/2023.
Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)- (d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e).
Failure to provide a certified translation may result in no benefit being accorded for the non-English application.
Claim Objections
Claims 13 and 20 are objected to because of the following informalities: the exemplified compounds in claims 13 and 20 are low resolution, making them difficult to interpret. Appropriate correction is required.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1–7, 9–10, 12–16, 18, and 20 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Duan et al. (CN 116284084 A, hereinafter “Duan”). An English translation has been provided in this Office Action.
Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216.
Regarding Claims 1 and 14, Duan discloses the organic light emitting device of Example 27 including an anode, a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, and a cathode [pg. 83], wherein the emission layer comprises compound M-429 [pg. 66] which reads on Applicant’s Formula 1 (shown below),
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wherein:
X and Y are each represented by Formula 2:
R1 to R5 are each hydrogen,
A1 to A5 are each deuterium,
Z1 to Z2 are each represented by Formula 3:
Za, Zb, and Zc are each N,
Ra is connected to Formula a,
Rb and Rc are each an unsubstituted aryl group having 6 ring-forming carbon atoms (phenyl).
Z3 to Z5 are each hydrogen.
Regarding Claim 2, Example 27 includes an anode, a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, and a cathode [pg. 83], wherein the emission layer comprises compound M-429 [pg. 66].
Regarding Claim 3, Duan teaches that MR-TADF materials, such as M-429, emit light by delayed fluorescence [pg. 2 and 87–88].
Regarding Claim 4, Example 27 has a maximum emission wavelength of 452 nm [Table 1].
Regarding Claims 5, 6, and 15, Formula 3 in M-429 is represented by Formula 3-1-7 and Formula 3-2-7 (shown below), wherein Rb, Rc, Rb1, and Rc1 are each an unsubstituted aryl group having 6 ring-forming carbon atoms (phenyl).
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Regarding Claims 7 and 16, M-429 reads on Applicant’s Formula 1-1-1 (shown below), wherein Z1a and Z2a are each represented by Formula 3, X, Y, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Regarding Claim 9, M-429 reads on Applicant’s Formula 1-3-3 (shown below), wherein R1a to R5a and R1b to R5b are each hydrogen, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Regarding Claims 10 and 18, M-429 reads on Applicant’s Formula 1-4 (shown below), wherein Xa and Ya are each represented by Formula 2-1, A1 to A5 and Z1 to Z6 are the same as defined in Formula 1.
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Regarding Claims 12, M-429 reads on Applicant’s Formula 1-6-2 (shown below), wherein Z3d to Z6d are each hydrogen, Z1c and Z2c are each represented by Formula 3, X, Y, and A1 to A5 are the same as defined in Formula 1
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Regarding Claim 13 and 20, Duan discloses the organic light emitting device of Example 4 including an anode, a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, and a cathode [pg. 81], wherein the emission layer comprises compound M-4 [pg. 56] which is identical to Applicant’s compound A-1 (shown below).
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Claims 14–16 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Fleetham et al. (US 2023/0363276 A1, hereinafter “Fleetham”).
Regarding Claim 14, Fleetham discloses Compound 1 [pg. 41] which reads on Applicant’s Formula 1 (shown below),
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wherein:
X and Y are each O:
A1 is a heteroaryl group having 12 ring-forming carbon atoms (carbazole) substituted with deuterium,
A2 to A5 are each deuterium,
Z1 to Z5 are each deuterium.
Regarding Claim 15, Compound 1 does not comprise a substituent represented by Formula 3. Therefore, Compound 1 reads on Applicant’s further limitation of Formula 3.
Regarding Claim 16, Compound 1 reads on Applicant’s Formula 1-1-1 (shown below), wherein Z1a is a cyano group, Z2a is a deuterium, and X, Y, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or 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 1–2, 5–7, 9, and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Fleetham et al. (US 2023/0363276 A1).
Regarding Claims 1–2, 5–7, 9, and 12, Fleetham teaches the organic light emitting device of Fig. 1 including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode [0158]. Fleetham teaches the compounds of present disclosure, such as Compound 1, may be used in the organic light emitting device [0110]. Fleetham further teaches the compounds of present disclosure may be used as a host [0117]. Additionally, Fleetham teaches the compound of present disclosure have a deeper LUMO level and therefore facilitate electron transporting in blue OLEDs resulting in an improved device performance [0229].
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to use Compound 1 in the organic light emitting device described by Fleetham, because this would have been combining the prior art elements of Fleetham according to known methods to yield predictable results of an organic light emitting device with the improved device performance, as taught by Fleetham. See MPEP 2143.I.(A).
Per Claims 1 and 2, the organic light emitting device, as described above, including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, wherein the emissive layer comprises Compound 1 as a host reads on Applicant’s limitation since Compound 1 reads on Applicant’s Formula 1 (shown below),
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wherein:
X and Y are each O:
A1 is a heteroaryl group having 12 ring-forming carbon atoms (carbazole) substituted with deuterium,
A2 to A5 are each deuterium,
Z1 to Z5 are each deuterium.
Per Claims 5 and 6, Compound 1 does not comprise a substituent represented by Formula 3. Therefore, Compound 1 reads on Applicant’s further limitation of Formula 3.
Per Claim 7, Compound 1 reads on Applicant’s Formula 1-1-1 (shown below), wherein Z1a is a cyano group, Z2a is a deuterium, and X, Y, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Per Claim 9, Compound 1 reads on Applicant’s Formula 1-3-1 (shown below), wherein A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Per Claim 12, Compound 1 reads on Applicant’s Formula 1-6-2, wherein Z1d to Z6d are each deuterium, Z2c is a cyano group, X, Y, and A1 to A5 are the same as defined in Formula 1
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Claims 1–20 are rejected under 35 U.S.C. 103 as being unpatentable over Kuwabara et al. (US 2021/0175423 A1, provided in Applicant’s IDS filed on 10/19/2023, hereinafter “Kuwabara”) in view of Geum et al. (US 2021/0277026 A1, hereinafter “Geum”), and evidenced by Wikipedia (Visible spectrum, provided in this Office Action, hereinafter “Wikipedia”).
Regarding Claims 14–18, Kuwabara teaches Compound 15 [pg. 12] which reads on Applicant’s Formula 1 (shown below),
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wherein:
X and Y are each represented by Formula 2:
R1 to R5 are each hydrogen,
A1 is an unsubstituted heteroaryl group having 12 ring-forming carbon atoms,
A2 to A5 are each hydrogen,
Z4 and Z5 are each a cyano group,
Z1 to Z3 and Z6 are each hydrogen.
However, Compound 15 fails to read on Applicant’s Formula 1 since it specifies that “when any one selected form among Z4 and Z5 is a cyano group, at least one selected from among R1 to R5 in Formula 2 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.”
Geum teaches compounds of Geum’s Formula 1 (shown below) [0012]. Specifically, Geum teaches ortho phenyl substituents on the phenyl linked the N of the core structure in the compound of Geum’s Formula 1 prevents aggregation of molecules, thereby minimizing the stacking between molecules so that it is possible to expect high efficiency when the compound is used in an organic light emitting device [0041]. Geum further teaches the substituent increases the stability of the molecule since it increases the steric hindrance around the empty orbital of the boron atom [0038] – [0039].
Additionally, Kuwabara’s Compound 15 is represented by Kuwabara’s Formula 1, which allows Ar1 and Ar2 to be an aryl group having 18 ring-forming carbon atoms (i.e. terphenyl, the substituent taught by Geum) [0009].
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to add ortho phenyl substituents to Compound 15 to form a terphenyl, based on the teaching of Kuwabara in view of Geum. The motivation for doing so would have been to increase the steric hindrance around the boron atom and thereby increase the stability of the molecule, as taught by Geum.
Per Claim 14, the modified version of Compound 15, as described above (hereinafter “Modified 15”), reads on Applicant’s Formula 1 (shown below),
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wherein:
X and Y are each represented by Formula 2:
R1 and R5 are each an unsubstituted aryl group having 6 ring-forming carbon atoms (phenyl),
R2 to R4 are each hydrogen,
A1 is an unsubstituted heteroaryl group having 12 ring-forming carbon atoms,
A2 to A5 are each hydrogen,
Z4 and Z5 are each a cyano group,
Z1 to Z3 and Z6 are each hydrogen.
Per Claim 15, Modified 15 does not comprise Formula 3. Therefore, Compound 15 reads on Applicant’s further limitation of Formula 3.
Per Claim 16, Modified 15 reads on Applicant’s Formula 1-1-2 (shown below), wherein Z4a is a cyano group, Z3a is a hydrogen, and X, Y, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Per Claim 17, Modified 15 reads on Applicant’s Formula 1-2-2 (shown below), wherein Z4a and Z5a are each a cyano group, Z3a and Z6a are each a hydrogen, and X, Y, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Per Claim 18, Modified 15 reads on Applicant’s Formula 1-4 (shown below), wherein Xa and Ya are each represented by Formula 2-4, R13 and R14 are each hydrogen, n3 and n4 are each 5, R2 to R4 are the same as defined in Formula 2, A1 to A5 and Z1 to Z6 are the same as defined in Applicant’s Formula 1.
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Regarding Claims 1–10, Kuwabara teaches an organic electroluminescence device including a first electrode, a hole transport region, an emission layer, an electron transport region, and a second electrode, wherein the emission layer comprises a compound represented by Kuwabara’s Formula 1, such as Modified 15, resulting in a high luminous efficiency [abstract].
However, Kuwabara fails to disclose an exemplified device comprising Modified 15.
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to use Modified 15 in the emission layer of the organic electroluminescence device taught by Kuwabara, because this would have been combining the prior art elements of Kuwabara according to known methods to yield predictable results of an organic electroluminescence device with a high luminous efficiency, as taught by Kuwabara. See MPEP 2143.I.(A).
Per Claims 1 and 2, the organic electroluminescence device, as described above (hereinafter “Device 1”), reads on Applicant’s limitation since it includes a first electrode, a hole transport region, an emission layer, an electron transport region, and a second electrode, wherein the emission layer comprises Modified 15, which reads on Applicant’s Formula 1 (shown below),
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wherein:
X and Y are each represented by Formula 2:
R1 and R5 are each an unsubstituted aryl group having 6 ring-forming carbon atoms (phenyl),
R2 to R4 are each hydrogen,
A1 is an unsubstituted heteroaryl group having 12 ring-forming carbon atoms,
A2 to A5 are each hydrogen,
Z4 and Z5 are each a cyano group,
Z1 to Z3 and Z6 are each hydrogen.
Per Claim 3, Kuwabara teaches the compounds represented by Kuwabara’s Formula 1, such as Modified 15, exhibit thermally activated delayed fluorescence [0007].
Per Claim 4, Kuwabara teaches the emission layer may be a delayed fluorescence emission layer to emit blue light [0012]. Kuwabara further teaches the compounds represented by Kuwabara’s Formula 1, such as Modified 15, may be used in an organic electroluminescence device with superior luminous efficiency and life span in the blue wavelength region [0148]. The blue wavelength region is from 450–485 nm, as evidenced by Wikipedia [pg. 2].
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to produce a device like Device 1, comprising Modified 15, which has a maximum emission wavelength in the range of 450–485 nm since Kuwabara teaches the device may emit light in the blue wavelength region. The motivation for doing so would have been to produce a device with superior luminous efficiency and lifespan in the blue wavelength region, as taught by Kuwabara.
Per Claims 5 and 6, Modified 15 does not comprise Formula 3. Therefore, Modified 15 reads on Applicant’s further limitation of Formula 3.
Per Claim 7, Modified 15 reads on Applicant’s Formula 1-1-2 (shown below), wherein Z4a is a cyano group, Z3a is a hydrogen, and X, Y, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Per Claim 8, Modified 15 reads on Applicant’s Formula 1-2-2 (shown below), wherein Z4a and Z5a are each a cyano group, Z3a and Z6a are each a hydrogen, and X, Y, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Per Claim 9, Modified 15 reads on Applicant’s Formula 1-3-3 (shown below), wherein R1a, R5a, R1b, and R5b are each an unsubstituted aryl group having 6 ring-forming carbon atoms (phenyl), R2a to R4a and R2b to R4b are each hydrogen, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Per Claim 10, Modified 15 reads on Applicant’s Formula 1-4 (shown below), wherein Xa and Ya are each represented by Applicant’s Formula 2-4, R13 and R14 are each hydrogen, n3 and n4 are each 5, R2 to R4 are the same as defined in Applicant’s Formula 2, A1 to A5 and Z1 to Z6 are the same as defined in Applicant’s Formula 1.
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Per Claims 12, Modified 15 reads on Applicant’s Formula 1-6-7 (shown below), wherein Z1d to Z3d and Z6d are each hydrogen, Z5c and Z4c are each a cyano group, X, Y, and A1 to A5 are the same as defined in Formula 1
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Regarding Claims 11 and 19, Modified 15 fails to read on Applicant’s Formula 1-5-4 since Z5b is represented by a cyano group instead of either Applicant’s Formula A-1 or A-2.
Kuwabara teaches Compound 3 [pg. 10] which comprises a carbazole at the same position as one of the cyano groups in Modified 15. Modified 15 and Compound 3 are both represented by Kuwabara’s Formula 1. Therefore, Kuwabara teaches a cyano group may be substituted with a carbazole in that position. Additionally, Kuwabara teaches organic electroluminescence devices comprising a compound of Kuwabara’s Formula 1 has a long service life and high efficiency [0006].
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Therefore, given the general formula and teachings of Kuwabara, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute a cyano group with a carbazole, because Kuwabara teaches the variable may suitably be selected as carbazole. The substitution would have been one preferred element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as emitter in the emission layer of the organic electroluminescence device of Kuwabara and possess the benefits taught by Kuwabara. See MPEP 2143.I.(B).
The further modified version of Modified 15, hereinafter “2nd Modified 15”, reads on Applicant’s Formula 1-5-4 (shown below), wherein Z5b and A1a are each represented by Formula A-2 (shown below), wherein Ra2 and Ra3 are each hydrogen, b2 and b3 are each 4, X, Y, A1 to A5, and Z1 to Z6 are the same as defined in Formula 1.
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Regarding Claim 13 and 20, Modified 15 fails to read on Applicant’s compound J-3 since it does not comprise tert-butyl groups on the carbazole.
Kuwabara teaches Compound 3 [pg. 10] which comprises tert-butyl groups on para position of the diphenylamine. Compound 3 and Modified 15 are both represented by Kuwabara’s Formula 6, wherein the diphenylamine, as shown in Compound 3, may be fused to form a carbazole, as shown in Modified 15. Therefore, Kuwabara teaches tert-butyl groups may be substituted onto a carbazole in the para position. Additionally, Kuwabara teaches organic electroluminescence devices comprising a compound of Kuwabara’s Formula 1 has a long service life and high efficiency [0006].
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Therefore, given the general formula and teachings of Kuwabara, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute a hydrogen in the para position of the carbazole with a tert-butyl group, because Kuwabara teaches the variable may suitably be selected as a tert-butyl group. The substitution would have been one preferred element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as emitter in the emission layer of the organic electroluminescence device of Kuwabara and possess the benefits taught by Kuwabara. See MPEP 2143.I.(B).
The further modified version of Modified 15, hereinafter “3rd Modified 15”, is identical to Applicant’s J-3 (shown below).
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Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JAMES RICHARD FORTWENGLER whose telephone number is (571)272-5433. The examiner can normally be reached Monday - Friday, 8 am - 5 pm.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Marla McConnell can be reached at (571) 270-7692. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/J.R.F./Examiner, Art Unit 1789
/MARLA D MCCONNELL/Supervisory Patent Examiner, Art Unit 1789
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