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. CN 202310349059.0, filed on 03/27/2023.
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.
Drawings
Under CFR 1.84(u), if only one drawing is shown, it must not be numbered and the abbreviation “FIG.” must not appear. Instead, the drawing should be labeled “the FIGURE”. Appropriate correction is required.
Specification
The specification is objected to because it references “FIG. 1” which must be changed to “the FIGURE”. Appropriate correction is required.
Claim Objections
Claim 4 is objected to because of the following informalities: Claim 4 recites “wherein R2, R4, and R4”. Instead, it should recite “wherein R2, R3, and R4”. Appropriate correction is required.
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 1–8, 11–15, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Imaizumi et al. (US 2021/0234104 A1, the US equivalent of CN 113121556 provided in Applicant’s IDS filed on 03/16/2026, hereafter “Imaizumi”).
Regarding Claims 1–2, 4–8, 11–13, and 20, Imaizumi teaches organic electroluminescent devices including a first electrode, a second electrode, and a plurality of organic layers between the electrodes wherein one layer comprises an amine compound represented by Formula 1 [0008], such as Compound A131 (shown below) [0024]. Imaizumi further teaches an organic electroluminescent device may show excellent emission efficiency when an amine compound of present disclosure is included [0242].
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However, Compound A131 does not read on Applicant’s Formula (1) since the tert-butyl is bonded to the dibenzofuran in the 2-position instead of the 1-position (shown above). Note that R4, represented by tert-butyl in Compound A131, does not have a specified bonding position.
Given the general formula and teachings of Imaizumi, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of Compound A131 wherein the tert-butyl is changed from the 2-position to the 1-position, as shown above. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Formula 1/the positional isomers of the compound represented by Compound A131 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as a hole transport material in the hole transport layer of the organic electroluminescent device of Imaizumi and possess the properties taught by Imaizumi. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP 2144.09 II.
Per Claim 1 and 20, the modified version of Compound A131 (hereafter “Modified A131”) reads on Applicant’s Formula (1) (shown below),
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wherein:
Ar1 and Ar2 are each an aromatic group with 6 ring atoms substituted with an aromatic group with 6 ring atoms (biphenyl),
Ar3 is a heteroaromatic group with 7 ring atoms (benzofuran) substituted with a tertbutyl group,
R1 is an unsubstituted tertbutyl group.
Per Claim 2, R1 is represented by
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in Modified A131.
Per Claims 4, 11, and 12, Ar1 and Ar2 are each represented by
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in Modified A131.
Per Claim 5, Ar1 and Ar2 are each represented by
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which does not include an X. Therefore, Applicant’s limitation of an optional substituent does not apply to Modified A131.
Per Claim 6,
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is represented by
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in Modified A131.
Per Claims 7, 8, and 13, Ar3 is represented by
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in Modified A131 wherein Y is O.
Regarding Claim 15, Modified A131 is nearly identical to Applicant’s Compound 1, however there is an additional tertbutyl group (shown below).
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Modified A131 is represented by Imaizumi’s Formula 4-3 (shown below) wherein the tertbutyl shown above is represented by R4. Note that R4 is not present when m is 0. Imaizumi teaches other compounds represented by Formula 4-3 wherein R4 is not present, such as Compound A92 (shown below) [0024]. Imaizumi further teaches an organic electroluminescent device may show excellent emission efficiency when an amine compound of present disclosure is included [0242].
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Therefore, given the general formula and teachings of Imaizumi, 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 tertbutyl for hydrogen, because Imaizumi teaches the variable may suitably be selected as tertbutyl, like in Compound A131, or hydrogen, like in Compound A92. 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 a hole transport material in the hole transport layer of the organic electroluminescent device of Imaizumi and possess the benefits taught by Imaizumi. See MPEP 2143.I.(B).
The modified version of Modified A131 (hereafter “2nd Modified A131”) reads on Applicant’s limitation since it is identical to Applicant’s Compound 1.
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Regarding Claims 3 and 14, 2nd Modified A131 is nearly identical to Applicant’s Compound 2 of claim 14, however the alkyl substituent is a tertbutyl instead of a methyl (shown below).
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2nd Modified A131 is represented by Imaizumi’s Formula 4-3 (shown below) wherein the tertbutyl shown above is represented by R5. Imaizumi teaches R5 may be an alkyl group [0010]. Imaizumi further teaches an alkyl group may be a methyl or a t-butyl group [0061]. Additionally, Imaizumi teaches an organic electroluminescent device may show excellent emission efficiency when an amine compound of present disclosure is included [0242].
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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 the tertbutyl of 2nd Modified A131 to be a methyl, because it would have been choosing from the possible alkyl group listed by Imaizumi, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the hole transport material in the hole transport layer of the organic electroluminescent device of Imaizumi and possessing the benefits taught by Imaizumi. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 4-3 having the benefits taught by Imaizumi in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Per Claim 3, the modified version of 2nd Modified A131 (hereafter “3rd Modified A131”) reads on Applicant’s limitation since R1 is represented by
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(shown below).
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Per Claim 14, 3rd Modified A131 is identical to Applicant’s Compound 2 (shown below).
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Claims 16–19 are rejected under 35 U.S.C. 103 as being unpatentable over Imaizumi et al. (US 2021/0234104 A1) as applied to claims 1–8, 11–15, and 20 above, and further in view of Jou et al. (US 2007/0236136 A1, hereafter “Jou”).
Regarding Claims 16–19, Imaizumi does not explicitly teach a composition of the compounds taught by Imaizumi and a solvent.
Imaizumi teaches the amine compound of present disclosure may be used in the hole transport region [0055]. Imaizumi further teaches the hole transport region may be formed by vacuum deposition, a spin-coating method, a cast method, a Langmuir-Blodgett method, an inkjet printing method, a laser printing method, and/or a laser induced thermal imaging method [0054]. A spin-coating method would involve a composition of the amine compound and an organic solvent.
Jou teaches a solution manufacturing process can provide a simpler and lower cost manufacturing process in comparison to vacuum deposition [0087].
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 a spin-coat method to deposit the hole transport layer including Modified A131 and an organic solvent, based on the teaching of Imaizumi. The motivation for doing so would have been to produce a device with a simpler and lower cost manufacturing process, as taught by Jou.
Per Claim 16, the composition of an organic solvent and Modified A131 to form the hole transport layer reads on Applicant’s limitation since Modified A131 reads on Applicant’s Formula (1) (shown below),
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wherein:
Ar1 and Ar2 are each an aromatic group with 6 ring atoms substituted with an aromatic group with 6 ring atoms (biphenyl),
Ar3 is a heteroaromatic group with 7 ring atoms (benzofuran) substituted with a tertbutyl group,
R1 is an unsubstituted tertbutyl group.
Per Claim 17, R1 is represented by
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in Modified A131.
Per Claims 18, Ar1 and Ar2 are each represented by
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in Modified A131.
Per Claims 19, Ar3 is represented by
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in Modified A131 wherein Y is O.
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Imaizumi et al. (US 2021/0234104 A1) as applied to claims 1–8, 11–15, and 20 above, and further in view of Li et al. (US 2002/0076576 A1, hereafter “Li”).
Regarding Claim 10, the methyl group of 3rd Modified A131 does not comprise a deuterium atom.
3rd Modified A131 is represented by Imaizumi’s Formula 4-3 (shown below) wherein the tertbutyl shown above is represented by R5. Imaizumi teaches R5 may be a substituted alkyl group [0010]. Imaizumi teaches an alkyl group may be a methyl [0061]. Imaizumi further teaches a deuterium atom as an option for a substituent [0056]. In fact, Imaizumi teaches Compound A100 wherein R1 is a phenyl substituted with deuterium atoms. Additionally, Imaizumi teaches an organic electroluminescent device may show excellent emission efficiency when an amine compound of present disclosure is included [0242].
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Li teaches the C-D bond is stronger than C-H meaning it is more stable and reacts more slowly than a carbon-hydrogen chemical bond. This leads to a deuterated organic system having better thermal stability, and longer lifetime in an optoelectronic device [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 deuterate the methyl group of 3rd Modified A131, based on the teaching of Imaizumi. The motivation for doing so would have been to increase the thermal stability of 3rd Modified A131 and increase the lifetime of an optoelectronic device comprising 3rd Modified A131, as taught by Li.
The modified version of 3rd Modified A131 (hereafter “4th Modified A131”) reads on Applicant’s limitation since R1 is a methyl group substituted with deuterium atoms (shown below).
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Claims 1–9, 11–12, and 14–20 are rejected under 35 U.S.C. 103 as being unpatentable over Ma et al. (CN 113620819 A, provided in Applicant’s IDS filed on 10/22/2025, hereafter “Ma”). An English translation was provided in this office action.
Regarding Claim 1–5, 7–8, and 16–20, Ma teaches an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers between the electrodes wherein one organic layer comprises a compound of present disclosure [pg. 10]. Specifically, Ma teaches Compound 52 (shown below) [pg. 6]. Additionally, Ma teaches the compounds of present disclosure were purified by column chromatography using dichloromethane and petroleum ether as solvents [pg. 12].
However, Compound 52 does not read on Applicant’s Formula (1) since the methyl of Compound 52, is in the 3-position instead of the 1-position of the dibenzofuran.
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As drawn, Compound 52 is benzannulated in the 1-position, blocking that position. However, Compound 52 is represented by Formula (I), and more specifically by Formula (I-1) (shown below). Ma also teaches Formula (I-6) which is not benzannulated in the 1-position. Ma further teaches that organic electroluminescent devices comprising the compounds of present invention have high luminous efficiency and long lifespans [pg. 2].
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Therefore, given the general formula and teachings of Ma, 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 Formula (I-1) for Formula (I-6) in Compound 52, because Ma teaches the variable may suitably be selected as Formula (I-1) or Formula (I-6). 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 an organic material in the light emitting auxiliary layer of the organic electroluminescent device of Ma and possess the benefits taught by Ma. See MPEP 2143.I.(B).
Additionally, given the general formula and teachings of Ma, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of Compound 52 wherein the methyl is moved from the 3-position to the 1-position. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Formula (I-6) in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as an organic material in the light emitting auxiliary layer of the organic electroluminescent device of Ma and possess the properties taught by Ma. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP 2144.09 II.
Per Claims 1, 16, and 20, the modified version of Compound A131 (hereafter “Modified A131”) reads on Applicant’s Formula (1) (shown below),
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wherein:
Ar1 is an aromatic group with 6 ring atoms (phenyl) substituted with a heteroaromatic group with 13 ring atoms (dibenzofuran),
Ar2 is an aromatic group with 6 ring atoms (phenyl) substituted with a C1 alkyl group (methyl),
Ar3 is an unsubstituted aromatic group with 6 ring atoms (phenyl),
R1 is an unsubstituted methyl group.
Note that Ma teaches an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers between the electrodes wherein one organic layer comprises a compound of present disclosure [pg. 10] reading on claim 20, and Ma teaches the compounds of present disclosure were purified by column chromatography using dichloromethane and petroleum ether as solvents [pg. 12] reading on claim 16.
Per Claims 2, 3, and 17, R1 is represented by
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in Modified 52.
Per Claims 4 and 18, Ar1 and Ar2 are each represented by
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wherein Ar1 is substituted by a C1 alkyl group (methyl) and Ar2 is substituted by a heteroaromatic group with 13 ring atoms (dibenzofuran).
Per Claim 5, Ar1 and Ar2 are each represented by
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which does not include an X. Therefore, Applicant’s limitation of an optional substituent does not apply to Modified 52.
Per Claims 7, 8, and 19, Ar3 is represented by
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in Modified 52.
Regarding Claims 6, 9, 11–12, and 14–15, Modified 52 does not comprise a structure listed in claim 6. Modified 52 comprises Moiety 1 which is represented by General Formula II (shown below) [pg. 3]. Ma also teaches Moiety 2 [pg. 3]. Ma further teaches that organic electroluminescent devices comprising the compounds of present invention have high luminous efficiency and long lifespans [pg. 2].
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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 substitute Moiety 2 for Moiety 1 in Modified 52, because it would have been choosing between the exemplified moieties listed by Ma [pg. 3], which would have been a choice from a finite number of identified, predictable solutions of a compound useful as an organic material in the light emitting auxiliary layer of the organic electroluminescent device of Ma and possess the properties taught by Ma. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Ma’s Formula (I) having the benefits taught by Ma in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Per Claim 6, the modified version of Modified 52 (hereafter “2nd Modified 52”) reads on Applicant’s limitation since
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is represented by
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(shown below).
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Per Claims 9, 11, and 12, Ar1 and Ar2 are each represented by
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, Ar3 is phenyl, and R1 is an unsubstituted methyl in 2nd Modified 52.
Per Claims 14 and 15, 2nd Modified 52 is identical to Applicant’s Compound 3 in claims 14 and 15 (shown below).
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Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Lee et al. (WO 2025/105913 A1, hereafter “Lee”) teaches compound 617 [pg. 52] (shown below) which reads on Applicant’s Formula (1). However, Lee does not predate Applicant’s priority date. An English translation of Lee was provided in this office action.
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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.
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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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