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 .
Summary of Claims
Claims 1, 2, and 7 are amended, claim 6 is cancelled due to Applicant's amendment dated 05/08/2026. Claims 1–5 and 7–10 are pending.
Response to Amendment
The rejection of claim 6 as set forth in the previous Office Action is moot because claim 6 is cancelled due to the Applicant's amendment dated 05/08/2026.
The rejections of claims 1, 3–5, and 7–10 under 35 U.S.C. 103 as being unpatentable over Kitamura et al. (WO 2012/014822 A1, hereinafter “Kitamura”) in view of Li et al. (US 2002/0076576 A1, hereinafter “Li”) are overcome due to the Applicant’s amendment dated 05/08/2026. Therefore, the rejections are withdrawn.
The rejections of claims 1, 2, 5, and 7–10 under 35 U.S.C. 103 as being unpatentable over Chen et al. (CN 107141191 A, hereinafter “Chen”) in view of Li are overcome due to the Applicant’s amendment dated 05/08/2026. Therefore, the rejections are withdrawn.
However, as outlined below, new grounds of rejection have been made due to the amendment.
Response to Arguments
Applicant's argument – On pages 11–14, Applicant argues that the deuteration of the compounds taught by Kitamura in view of Li would not be obvious because the claimed compounds provide surprising and unexpected improvements relative to Kitamura. Specifically, Applicant argues that life-span T96 of Compound 1-3 is 21% better than the not deuterated Compound A1, and 13% better than Compound B1 which is allegedly within the scope of Kitamura (see Table 1 of the Declaration filed on 05/08/2026).
Examiner's response – Applicant’s argument is not persuasive for at least the following reasons. Overcoming a rejection based on unexpected results requires at least the combination of three different elements: (i) the results must fairly compare with the closest prior art in an affidavit or declaration under 37 CFR 1.132, (ii) the claims must be commensurate in scope, and (iii) the results must truly be unexpected. MPEP 716.02. Additionally, the burden rests with Applicant to establish the results are unexpected and significant. MPEP 716.02(b).
Comparison with closest prior art
On pages 12 –14, Applicant argues that Compound 1-3 shows unexpected results due to the spirobifluorene being substituted at the 4-position. However, Applicant has not at least made a comparison to the closest prior art of Kitamura’s Compound 1. It differs from Applicant’s Compound 1-3 by both the degree of deuteration and the positioning of the spirobifluorene group. As the compounds differ by these variables, a comparison is not being made to the closest prior art. Where the comparison is not identical with the reference disclosure, deviations therefrom should be explained, and if not explained should be noted and evaluated, and if significant, explanation should be required. MPEP 716.02(e).
Commensurate in Scope
Applicant’s Compound 1-3 is a fully deuterated compound represented by the claimed Chemical Formula I-4, whereas claim 1 only requires L1 is an arylene or heterocyclic group substituted with at least one deuterium or at least one of R1 to R7 is deuterium. Accordingly, the data is not commensurate in scope with the claims.
The data shown in Table 1 is not commensurate in scope with the claimed invention for at least the reasons that the data is shown for the use of a compound in the light emitting layer of a device, whereas the claim is directed to a compound. The improved properties of life-span T96 % are shown when the compound is used in a light emitting layer of an OLED (and with other particular compounds present in the same layer). None of these limitations are required by the claim. No evidence has been provided to show that the unexpected results would be present for the use of the compound in other layers (or with other compounds present in the same layer).
Additionally, as claims 8 and 9 claim a broad device structure including any materials, but the device discussed in the instant specification (Example 1) only recite one specific device structure and materials (see instant [00153] – [00159]). Therefore, the data is not commensurate in scope with the claims.
Unexpected Results
While there is an improvement in life-span T96 % between the device comprising Compound 1-3 in comparison to the device comprising Compound A1 and the device comprising Compound B1, it is unclear whether these performances are truly unexpected.
As discussed in the rejection below, Li teaches the carbon-deuterium bond is stronger, more stable, and reacts more slowly than the carbon-hydrogen bond, so a deuterated organic system has better thermal stability, and longer lifetime in optoelectronic devices [0009]. Therefore, one would expect the life-span T96 % to increase by deuterating the compounds taught by Kitamura. The extent to that increase is what would be unexpected. Applicant has not provided objective data for the life-span of the devices fabricated, and has instead provided comparative percentage values wherein the device comprising Compound 1-3 is set to 100%. It would be useful to see the raw data when analyzing the alleged unexpected increase the life-span T96 values.
Compound 1-3 comprise a different structure than Compounds A1 and B1. One of ordinary skill in the art would expect some difference between compounds having different structures and thus the compounds and the devices comprising the different compounds would be expected to result in some difference in properties, including life-span. Thus, in light of the teachings of Li and given that one of ordinary skill in the art would expect some degree of difference between compounds having different structures, it is unclear whether the degree of improvement shown by the data in the Declaration is truly unexpected.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1–5 and 7–10 are rejected under 35 U.S.C. 103 as being unpatentable over Kitamura et al. (WO 2012014822 A1, hereinafter “Kitamura”) in view of Li et al. (US 2002/0076576 A1, hereinafter “Li”).
Regarding Claims 1–5 and 7–10, 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]. Compound 1 nearly reads on Applicant’s Chemical Formula I-4 (shown below), wherein L1 is a phenylene substituted with hydrogen, and R1–R7 are hydrogen atoms.
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However, Chemical Formula I-4 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. Additionally, the attachment of Compound 1 is in the 2-position instead of the 4-position which is required by Applicant’s Chemical Formula I-4. Accordingly, Kitamura’s Compound 1 fails to read on the claimed Chemical Formula I-4.
Regarding the deuteration, Li 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 each hydrogen atom 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.
Regarding the positional isomer, Compound 1 is represented by Kitamura’s General Formula (1) wherein two or more RB’s may bond with each other and with the benzene ring B to form a fluorene ring [0047]. Kitamura does not specify where the RB’s are positioned relative to ring B, therefore the resulting fluorene ring may be in the 4-position instead of the 2-position. Additionally, Kitamura teaches an organic light-emitting element comprising the compounds of present invention have excellent luminous efficiency, durability, and a low operating voltage [0024].
Given the general formula and teachings of Kitamura, 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 1 wherein the attachment of the phenyl to the spirobifluorene is in the 4-position instead of the 2-position. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by General Formula (1) in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as a host in the light emitting layer of the organic light emitting device of Kitamura and possess the properties taught by Kitamura. 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, the fully deuterated positional isomer of Compound 1, as described above, (hereinafter “Modified Compound 1”) reads on Applicant’s Chemical Formula I-4 (shown below),
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wherein:
L1 is a C6 arylene group (phenylene) substituted with deuterium,
R1 to R7 are each deuterium,
m1 to m5 are each 4, while m6 and m7 are each 3.
Regarding Claim 2, R1 to R7 are each deuterium in Modified Compound 1.
Regarding Claim 3, L1 is a C6 arylene group fully substituted with deuterium and R1 to R7 are each deuterium in Modified Compound 1.
Regarding Claim 4, L1 is a phenylene group fully substituted with deuterium in Modified Compound 1.
Regarding Claim 5, R1 to R7 are each deuterium in Modified Compound 1.
Regarding Claim 7, Modified Compound 1 is identical to compound [1-4] in Group 1 (shown below).
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Regarding Claims 8 and 9, 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], such as Modified Compound 1. Kitamura further teaches the compound of 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].
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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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/J.R.F./Examiner, Art Unit 1789
/BRAELYN R WATSON/Primary Examiner, Art Unit 1786
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