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. KR 10-2021-0117782, filed on 3 September 2021. The certified copy has been filed in parent Application No. KR 10-2022-0110104, filed on 31 August 2022.
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, 3–10 are rejected under 35 U.S.C. 103 as being unpatentable over Kitamura et al. (Pub. No.: WO 2012014822 A1, Pub. Date: 2 February 2012) (hereafter Kitamura) in view of Li et al. (U.S. Pub. No.: US 2002/0076576 A1, Pub. Date: 20 June 2002) (hereafter Li). An English translation of Kitamura is provided within the non-final office action.
Kitamura teaches General Formula (1), which is exemplified by Compound 1 (shown below), wherein RA is a phenyl group, p is 1, q is 1 [0034], and RB is two fluorene rings bonded together (spirobifluorene) [0047]. Notably, Kitamura specifies that when the General Formula (1) has a hydrogen atom, it also includes isotopes (deuterium atoms etc.). In this case, all hydrogen atoms in the compound may be replaced with an isotope, or the compound may be a mixture of compounds some of which contain an isotope [0035].
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Regarding Claim 1, Compound 1 teaches Applicants’ Chemical Formula I (shown below), wherein L1 is a phenylene substituted with hydrogen, and R1–R7 are hydrogen atoms. However, Chemical Formula I requires that either L1 is a C6 to C20 arylene group substituted with at least one deuterium, or at least one of R1 to R7 is deuterium, or both, which is not taught by Kitamura.
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Li et al. teaches that hydrogens heavier isotope, deuterium, lies lower in the potential well, and hence has a lower zero-point energy and vibrational frequency. The smaller C-D stretching and bending motion, relative to C-H, results in a smaller van der Waals radius for D than for H resulting in a shorter bond. The shorter carbon-deuterium bonds are stronger, more stable, and react more slowly than carbon-hydrogen chemical bonds. Additionally, Li teaches that there is an improvement in optoelectronic device operational lifetime when deuterated organic molecules are used rather than hydrogenated organic molecules [0008] – [0009].
Therefore, it would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to modify Compound 1, taught by Kitamura, by replacing all of the hydrogen atoms with deuterium atoms, based on the teachings of Li. The motivation for doing so would be to increase the stability of the compound. Additionally, they would reasonably expect a predictable improvement in the operational lifetime of an optoelectronic device using the deuterated compound over the fully hydrogenated compound, as taught by Li.
Hereafter the fully deuterated version of Compound 1, where all of the hydrogens are replaced with deuterium will be called perdeuterated Compound 1.
Regarding claim 3, perdeuterated Compound 1 reads on Applicants’ limitation since L1 is a C6 arylene group fully substituted with deuterium and R1–R7 are deuterium.
Regarding claim 4, perdeuterated Compound 1 reads on Applicant’s limitation since L1 is a phenylene group fully substituted with deuterium.
Regarding claim 5, perdeuterated Compound 1 reads on Applicants’ limitation since R1–R7 are deuterium.
Regarding claim 6, perdeuterated Compound 1 reads on Chemical Formula I–2, shown below.
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Regarding claim 7, Compound 1, taught by Kitamura and described above, also does not read on the compounds of Group 1 in claim 7.
However, It would have been obvious to modify Compound 1, taught by Kitamura, by deuterating every position except for the 1-position of the spirobifluorene to arrive at compound [1-31] (shown below), because it would have been a choice of either a hydrogen or a deuterium at each position, which would have been a choice from a finite number of identified, predictable solutions of a compound useful in an organic layer of an organic light-emitting diode device taught by Kitamura and possessing the device operational lifetime benefits taught by Li. One of ordinary skill in the art would have been motivated to produce additional compounds comprising deuterium instead of hydrogen having the benefits taught by Li in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
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Regarding claims 8, modified Kitamura teaches an organic electroluminescent device consisting of an anode and a cathode with at least one organic layer including a light-emitting layer between the electrodes, wherein at least one of the organic layers contains a compound represented by General Formula (1) [0028], as modified above.
Regarding claim 9, modified Kitamura teaches an organic electroluminescent device consisting of an anode and a cathode with at least one organic layer including a light-emitting layer between the electrodes, wherein at least one of the organic layers contains a compound represented by General Formula (1) [0028], as modified above. The compound by General Formula (1) is preferably contained in the light-emitting layer [0068].
Regarding claim 10, Kitamura teaches that the organic light-emitting device of present invention can be used as a display device such as a television, a personal computer, a mobile phone, etc. [0308].
Claims 1, 2, 5–10 are rejected under 35 U.S.C. 103 as being unpatentable over Chen et al. (Pub. No.: CN 107141191 A, Pub. Date: 8 September 2017) (hereafter Chen) in view of Li et al. (U.S. Pub. No.: US 2002/0076576 A1, Pub. Date: 20 June 2002) (hereafter Li). An English translation of Chen is provided within the non-final office action.
Chen teaches formula (1) which is exemplified by compound 1-112 (shown below), wherein L1 is a single bond, and R1 is a C18 ring system (triphenylene) substituted with hydrogen atoms. Notably, Chen recites that R1 can be substituted in each occurrence, either identically or differently, from: hydrogen, deuterium, etc. [0022].
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Regarding claim 1, Compound 1-112 of Chen teaches Applicants’ Chemical Formula I (shown below), wherein L1 is a single bond, R1–R7 are hydrogen atoms. However, Chemical Formula I requires that either L1 is a C6 to C20 arylene group substituted with at least one deuterium, or at least one of R1 to R7 is deuterium, or both, which is not taught by Chen.
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Li et al. teaches that hydrogens heavier isotope, deuterium, lies lower in the potential well, and hence has a lower zero-point energy and vibrational frequency. The smaller C-D stretching and bending motion, relative to C-H, results in a smaller van der Waals radius for D than for H resulting in a shorter bond. The shorter carbon-deuterium bonds are stronger, more stable, and react more slowly than carbon-hydrogen chemical bonds. Additionally, Li teaches that there is an improvement in optoelectronic device operational lifetime when deuterated organic molecules are used rather than hydrogenated organic molecules [0008] – [0009].
Therefore, it would have been obvious for a person having ordinary skill in the art before the effective filing date of the claimed invention to modify compound 1-112, taught by Chen, by changing the hydrogen atoms on the triphenylene to deuterium atoms, based on the teachings of Li. The motivation for doing so would be to increase the stability of the compound. Additionally, they would reasonably expect a predictable improvement in the operational lifetime of an optoelectronic device using the deuterated compound over the hydrogenated compound, as taught by Li. Hereafter the deuterated version of compound 1-112, where all of the hydrogen atoms on the triphenylene are replaced with deuterium, will be called deuterated compound 1-112.
Regarding claim 2, deuterated compound 1-112 reads on Applicants’ limitation since L1 is a single bond, while R1, R2, and R6 are deuterium atoms.
Regarding claim 5, deuterated compound 1-112 reads on Applicants’ limitation since R1, R2, and R6 are deuterium atoms.
Regarding claim 6, deuterated compound 1-112 reads on Chemical Formula I–3, shown below.
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Regarding claim 7, deuterated compound 1-112 reads on Applicants’ compound [1-14].
Regarding claims 8, Chen teaches an electronic device comprising at least one compound that is represented by formula (1), such as deuterated compound 1-112, as modified above, wherein that electroluminescent device is an organic light-emitting diode [0091]. Organic electroluminescent devices generally include an anode, a metal cathode, and an organic layer sandwiched between them [0006] – [0007].
Regarding claim 9, Chen teaches that compounds represented by formula (1), such as deuterated compound 1-112, as modified above, can be used in any one or more layers of an electroluminescent device, but preferably used in the light-emitting layer [0093], reading on Applicants’ limitation.
Regarding claim 10, Chen teaches that organic electroluminescence from organic light-emitting diodes has applications in flat panel displays and lighting [0006].
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.
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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