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. JP 2020-168512, filed on 10/05/2020.
Acknowledgment is made of applicant's claim for foreign priority based on an application filed in Japan on 01/22/2021. It is noted, however, that applicant has not filed a certified copy of the JP 2021-008796 application as required by 37 CFR 1.55.
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 1–6, 9, 12–23, 29 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 2020/0127214 A1, hereafter “Choi”).
Regarding Claims 1–6, 9, 12–13, 15–17, 19–21, Choi teaches the organic light emitting diode of Example 1 including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emitting material layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode wherein the emitting material layer comprises TH-1, TD-1, and FD [0225]. TH-1 has a higher excited state singlet energy level than TD-1, and TD-1 has a higher excited state singlet energy level than FD [0010]. Choi further teaches Figure 4 which displays the energy relationship of TH-1 (Compound 1), TD-1 (Compound 2), and FD (Compound 3) (shown below). The energy relationship taught by Choi is very similar to the energy relationship taught by Applicant in Figure 5 of the instant application, wherein TH-1 corresponds to Compound M3, TD-1 corresponds to Compound M2, and FD corresponds to Compound M1 (shown below).
PNG
media_image1.png
555
576
media_image1.png
Greyscale
PNG
media_image2.png
392
588
media_image2.png
Greyscale
Choi teaches TD-1 (corresponding to Applicant’s Compound M2) has the delayed fluorescent property [0114]. TH-1 nearly reads on Applicant’s Formula (13), it is missing a carbazole bonded to the core carbazole (shown below).
PNG
media_image3.png
215
530
media_image3.png
Greyscale
PNG
media_image4.png
210
309
media_image4.png
Greyscale
TH-1 is represented by Choi’s Chemical Formula 1 [0011] (shown below). Choi further teaches compounds of Chemical Formula 1 may be applied to an organic light emitting device resulting in an excellent luminous efficiency and improved luminous lifespan [0100]. Choi also teaches compounds of Chemical Formula 1 may be used with a delayed fluorescent material in the emissive material layer of an organic light emitting device to reduce the driving voltage and power consumption [0101]. Additionally, Choi teaches Compound 1 which is also represented by Choi’s Chemical Formula 1,
PNG
media_image5.png
227
498
media_image5.png
Greyscale
PNG
media_image6.png
400
222
media_image6.png
Greyscale
wherein:
X is O,
Y is S,
R3 is a C12 heteroaryl group (carbazole),
R1, R2, R4 to R15 are each hydrogen.
However, Compound 1 does not read on Applicant’s Formula (13) because the carbazole bonded to the core carbazole is bonded in the wrong position and is bonded through the nitrogen to form a nitrogen-carbon bond. Choi’s Chemical Formula 1 does not specify which position the carbazole substituent may be bonded and it does not specify that the carbazole substituent must be bonded through a nitrogen-carbon bond instead of a carbon-carbon bond.
Given the general formula and teachings of Choi, 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 R4 is substituted with carbazole instead of R3 and the carbazole is bonded through a carbon-carbon bond instead of a nitrogen-carbon bond. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Chemical Formula 1/the positional isomers of the compound represented by Compound 1 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as the host in the emitting material layer of the organic light emitting device of Choi and possess the properties taught by Choi. 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 organic light emitting device (hereafter “Device 1”) including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emitting material layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode wherein the emitting material layer comprises the modified version of Compound 1 (hereafter “Modified Compound 1”), TD-1, and FD reads on Applicant’s limitation since TD-1 (corresponding to Applicant’s Compound M2) is a delayed fluorescent compound, and Modified Compound 1 (corresponding to Applicant’s Compound M3) reads on Applicant’s Formula (13) (shown below),
PNG
media_image7.png
210
530
media_image7.png
Greyscale
PNG
media_image8.png
363
401
media_image8.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L1 and L2 are each a single bond,
R11 to R14 and R16 to R18 are each hydrogen,
R21 to R26 and R28 are each hydrogen,
R27 is bonded to *1,
X1 is an oxygen atom,
R31, R32, R34 to R37 are each hydrogen,
R33 is bonded to *,
R38 is a substituent which is a heterocyclic group having 13 ring atoms (dibenzothiophene).
Additionally, since Modified Compound 1 is a compound of Choi’s Chemical Formula 1, it will have a higher singlet energy than TD-1, reading on Applicant’s Numerical Formula 1.
Per Claim 2, Device 1, as described above, also comprises FD, which corresponds to Applicant’s Compound M1. Choi teaches TD-1 (corresponding to Applicant’s Compound M2) has a higher excited state singlet energy level than FD (corresponding to Applicant’s Compound M1) [0010], reading on Applicant’s Numerical Formula 2.
Per Claim 3, Device 1 reads on Applicant’s limitation since no adjacent R11 to R18 are mutually bonded in Modified Compound 1.
Per Claim 4, Device 1 reads on Applicant’s limitation since no adjacent R21 to R28 are mutually bonded in Modified Compound 1.
Per Claim 5, Device 1 reads on Applicant’s limitation since no adjacent R31 to R38 are mutually bonded Modified Compound 1.
Per Claim 6, Device 1 reads on Applicant’s limitation since R11 to R14 and R16 to R18 are each hydrogen, R21 to R26 and R28 are each hydrogen, R27 is bonded to *1, R31, R32, R34 to R37 are each hydrogen, R33 is bonded to *, R38 is a substituent which is a heterocyclic group having 13 ring atoms (dibenzothiophene) in Modified Compound 1. R39 is not present since X1 is an oxygen atom.
Per Claim 9, Device 1 reads on Applicant’s limitation since L1 and L2 are each a single bond in Modified Compound 1.
Per Claims 12 and 13, Device 1 reads on Applicant’s limitation since X1 is an oxygen atom in Modified Compound 1.
Per Claims 15, 16, 17, Device 1 reads on Applicant’s limitation since Modified Compound 1 (corresponding to Applicant’s Compound M3) reads on Applicant’s Formula (117), wherein R11 to R18, R21 to R28, R31 to R39, X1, L1, L2, A2 are each the same as defined in Formula (13) above.
PNG
media_image9.png
260
562
media_image9.png
Greyscale
PNG
media_image8.png
363
401
media_image8.png
Greyscale
Per Claims 19 and 20, Device 1 reads on Applicant’s limitation since TD-1 (corresponding to Applicant’s Compound M2) reads on Applicant’s Formula (2) (shown below),
PNG
media_image10.png
214
238
media_image10.png
Greyscale
PNG
media_image11.png
359
261
media_image11.png
Greyscale
PNG
media_image12.png
210
305
media_image12.png
Greyscale
PNG
media_image13.png
174
138
media_image13.png
Greyscale
PNG
media_image14.png
131
139
media_image14.png
Greyscale
wherein:
n is 1,
m is 1,
q is 1,
CN is a cyano group,
D1 is represented by Formula (2b) wherein p is 2, A is represented by Formula (211) in once instance and Formula (212) in another instance (forming an indolocarbazole), R21 to R28, R2009, R2010 are each hydrogen, X201 is NR2013 wherein R2013 is an unsubstituted aryl group having 6 ring carbon atoms (phenyl),
RX is a heterocyclic group having 6 ring atoms (triazine) substituted with two aryl groups having 6 ring carbon atoms (phenyls).
Per Claim 21, Choi teaches the organic light emitting device of present disclosure may be applied to a display device and an illumination device [0025].
Regarding Claims 1, 22, 23, 29, Modified Compound 1 does not read on Applicant’s Formulae (121) to (122).
Choi’s Chemical Formula 1 does not specify the bonding position of the carbazole to the central dibenzofuran of Modified Compound 1.
PNG
media_image5.png
227
498
media_image5.png
Greyscale
Given the general formula and teachings of Choi, 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 Modified Compound 1 wherein the carbazole is bonded to a different position of the central dibenzofuran. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Chemical Formula 1/the positional isomers of the compound represented by Compound 1 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as the host in the emitting material layer of the organic light emitting device of Choi and possess the properties taught by Choi. 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, Device 1, as described above, comprising the modified version of Compound 1 (hereafter “Second Modified Compound 1”) reads on Applicant’s limitation since Second Modified Compound 1 reads on Applicant’s Formula (13) (shown below),
PNG
media_image7.png
210
530
media_image7.png
Greyscale
PNG
media_image15.png
274
416
media_image15.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L1 and L2 are each a single bond,
R11 to R14 and R16 to R18 are each hydrogen,
R21 to R26 and R28 are each hydrogen,
R27 is bonded to *1,
X1 is an oxygen atom,
R31 to R33 and R35 to R37 are each hydrogen,
R34 is bonded to *,
R38 is a substituent which is a heterocyclic group having 13 ring atoms (dibenzothiophene).
Per Claims 22, 23, 29, Device 1 reads on Applicant’s limitation since Second Modified Compound 1 (corresponding to Applicant’s Compound M3) reads on Applicant’s Formula (121), wherein R11 to R18, R21 to R28, R31 to R39, X1, L1, L2, A2 are each the same as defined in Formula (13) above.
PNG
media_image16.png
329
437
media_image16.png
Greyscale
PNG
media_image15.png
274
416
media_image15.png
Greyscale
Regarding Claims 1, 14, 17, and 18, Modified Compound 1 does not read on Applicant’s Formulae (111) to (114).
As discussed above, Choi’s Chemical Formula 1 does not specify which position the carbazole substituent may be bonded and it does not specify that the carbazole substituent must be bonded through a nitrogen-carbon bond instead of a carbon-carbon bond.
PNG
media_image5.png
227
498
media_image5.png
Greyscale
PNG
media_image6.png
400
222
media_image6.png
Greyscale
Therefore, given the general formula and teachings of Choi, 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 R1 is substituted with carbazole instead of R3 and the carbazole is bonded through a carbon-carbon bond instead of a nitrogen-carbon bond. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Chemical Formula 1/the positional isomers of the compound represented by Compound 1 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as the host in the emitting material layer of the organic light emitting device of Choi and possess the properties taught by Choi. 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, Device 1 comprising the modified version of Compound 1 (hereafter “Third Modified Compound 1”) as described above reads on Applicant’s limitation since Third Modified Compound 1 reads on Applicant’s Formula (11) (shown below),
PNG
media_image17.png
272
464
media_image17.png
Greyscale
PNG
media_image18.png
372
300
media_image18.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L1 and L2 are each a single bond,
R11 to R17 are each hydrogen,
R21 to R25 and R27 to R28 are each hydrogen,
R26 is bonded to *1,
X1 is an oxygen atom,
R31, R32, R34 to R37 are each hydrogen,
R33 is bonded to *,
R38 is a substituent which is a heterocyclic group having 13 ring atoms (dibenzothiophene).
Per Claims 14, 17, 18, Device 1 reads on Applicant’s limitation since Third Modified Compound 1 (corresponding to Applicant’s Compound M3) reads on Applicant’s Formula (111), wherein R11 to R18, R21 to R28, R31 to R39, X1, L1, L2, A2 are each the same as defined in Formula (11) above.
PNG
media_image19.png
284
453
media_image19.png
Greyscale
PNG
media_image18.png
372
300
media_image18.png
Greyscale
Claims 1–12, 14–26, 29, 34–35 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 2020/0127214 A1) in view of Ahn et al. (WO 2014/061991 A1, hereafter “Ahn”).
Regarding Claims 1–9, 12, 19–22, 25–26, 29, 35, Choi teaches the organic light emitting diode of Example 1 including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emitting material layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode wherein the emitting material layer comprises TH-1, TD-1, and FD [0225]. TH-1 has a higher excited state singlet energy level than TD-1, and TD-1 has a higher excited state singlet energy level than FD [0010]. Choi further teaches Figure 4 which displays the energy relationship of TH-1 (Compound 1), TD-1 (Compound 2), and FD (Compound 3) (shown below). The energy relationship taught by Choi is very similar to the energy relationship taught by Applicant in Figure 5 of the instant application, wherein TH-1 corresponds to Compound M3, TD-1 corresponds to Compound M2, and FD corresponds to Compound M1 (shown below). Choi teaches TD-1 (corresponding to Applicant’s Compound M2) has the delayed fluorescent property [0114]. Additionally, Choi teaches TH-1 functions as a host in the emitting material layer [0025].
PNG
media_image1.png
555
576
media_image1.png
Greyscale
PNG
media_image2.png
392
588
media_image2.png
Greyscale
Ahn teaches compounds which may be used in the light emitting layer as a host material [65]. Ahn teaches the compounds show high luminous efficiency and long lifespan. Ahn further teaches electroluminescent devices comprising these compounds can be operated at a low driving voltage and have improved current efficiency and lifespan [23]. Specifically, Ahn teaches C-97 [50].
PNG
media_image20.png
274
421
media_image20.png
Greyscale
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 TH-1, taught by Choi, with C-97, taught by Ahn, based on the teaching of Ahn. The motivation for doing so would have been to produce a device with a low driving voltage and improved current efficiency and lifespan, as taught by Ahn.
Per Claim 1, the organic light emitting device (hereafter “Device 2”) including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emitting material layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode wherein the emitting material layer comprises C-97, TD-1, and FD reads on Applicant’s limitation since TD-1 (corresponding to Applicant’s Compound M2) is a delayed fluorescent compound, and C-97 (corresponding to Applicant’s Compound M3) reads on Applicant’s Formula (12) (shown below),
PNG
media_image21.png
307
423
media_image21.png
Greyscale
PNG
media_image20.png
274
421
media_image20.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L1 is an unsubstituted arylene group having 12 ring carbon atoms (parabiphenylene) and L2 is a single bond,
R11 to R16 and R18 are each hydrogen,
R21 to R25 and R27 to R28 are each hydrogen,
R26 is bonded to *1,
X1 is a sulfur atom,
R31, R33 to R38 are each hydrogen,
R32 is bonded to *,
Additionally, since C-97 functions as a host material, as taught by Ahn, it is expected to have a high singlet energy. However, Ahn appears silent with respect to the singlet energy of C-97 being higher than compound M2.
The instant specification recites that M3-5 may be used as compound M3 [0452].
PNG
media_image22.png
175
249
media_image22.png
Greyscale
PNG
media_image20.png
274
421
media_image20.png
Greyscale
Since Ahn teaches C-97, a substantially identical structure as disclosed by the Applicant, the property of singlet energy being higher than compound M2 is considered to be inherent (and would be expected to fall within the range in the claim), absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP 2112.
Therefore, Device 2 reads on Applicant’s Numerical Formula 1.
Per Claim 2, Device 2, as described above, also comprises FD, which corresponds to Applicant’s Compound M1. Choi teaches TD-1 (corresponding to Applicant’s Compound M2) has a higher excited state singlet energy level than FD (corresponding to Applicant’s Compound M1) [0010], reading on Applicant’s Numerical Formula 2.
Per Claim 3, Device 2 reads on Applicant’s limitation since no adjacent R11 to R18 are mutually bonded in C-97.
Per Claim 4, Device 2 reads on Applicant’s limitation since no adjacent R21 to R28 are mutually bonded in C-97.
Per Claim 5, Device 2 reads on Applicant’s limitation since no adjacent R31 to R38 are mutually bonded in C-97.
Per Claims 6, 7, and 8, Device 2 reads on Applicant’s limitation since R11 to R16 and R18 are each hydrogen, R21 to R25 and R27 to R28 are each hydrogen, R26 is bonded to *1, R31, R33 to R37 are each hydrogen, R32 is bonded to * in C-97. R39 is not present since X1 is a sulfur atom.
Per Claim 9, Device 2 reads on Applicant’s limitation since L1 is an unsubstituted arylene group having 12 ring carbon atoms (parabiphenylene) and L2 is a single bond in C-97.
Per Claim 12, Device 2 reads on Applicant’s limitation since X1 is a sulfur atom in C-97.
Per Claims 19 and 20, Device 2 reads on Applicant’s limitation since TD-1 (corresponding to Applicant’s Compound M2) reads on Applicant’s Formula (2) (shown below),
PNG
media_image10.png
214
238
media_image10.png
Greyscale
PNG
media_image11.png
359
261
media_image11.png
Greyscale
PNG
media_image12.png
210
305
media_image12.png
Greyscale
PNG
media_image13.png
174
138
media_image13.png
Greyscale
PNG
media_image14.png
131
139
media_image14.png
Greyscale
wherein:
n is 1,
m is 1,
q is 1,
CN is a cyano group,
D1 is represented by Formula (2b) wherein p is 2, A is represented by Formula (211) in once instance and Formula (212) in another instance (forming an indolocarbazole), R21 to R28, R2009, R2010 are each hydrogen, X201 is NR2013 wherein R2013 is an unsubstituted aryl group having 6 ring carbon atoms (phenyl),
RX is a heterocyclic group having 6 ring atoms (triazine) substituted with two aryl groups having 6 ring carbon atoms (phenyls).
Per Claim 21, Choi teaches the organic light emitting device of present disclosure may be applied to a display device and an illumination device [0025].
Per Claims 22 and 29, Device 2 reads on Applicant’s limitation since C-97 reads on Applicant’s Formula (122) wherein R11 to R18, R21 to R28, R31 to R39, X1, L1, L2, A2 are each the same as defined in Formula (12) above.
PNG
media_image23.png
375
414
media_image23.png
Greyscale
PNG
media_image20.png
274
421
media_image20.png
Greyscale
Per Claims 25 and 35, Device 2 reads on Applicant’s limitation since C-97 reads on Applicant’s Formula (142) (shown below),
PNG
media_image24.png
326
474
media_image24.png
Greyscale
PNG
media_image20.png
274
421
media_image20.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L2 is a single bond,
R11 to R16 and R18 are each hydrogen,
R21 to R25 and R27 to R28 are each hydrogen,
R26 is bonded to *1,
X1 is a sulfur atom,
R31, R33 to R38 are each hydrogen,
R32 is bonded to *,
n1 is 2, R100 is a hydrogen.
Per Claim 26, Device 2 reads on Applicant’s limitation since C-97 reads on Applicant’s Formula (142A) wherein R11 to R18, R21 to R28, R31 to R39, X1, L1, L2, A2 are each the same as defined in Formula (142) above, n1 is 2, and R100 is a hydrogen.
PNG
media_image25.png
342
558
media_image25.png
Greyscale
PNG
media_image20.png
274
421
media_image20.png
Greyscale
Regarding Claims 10 and 11, C-97 does not read on Applicant’s limitation since L1 and L2 are not each a parabiphenylene. C-97 is represented by Ahn Formula (1) [10]. Ahn also teaches C-16 wherein Ar2 is an C18 aryl (terphenyl) [35]. Ahn also notes that Ar1 and L2 may be linked together to form a nitrogen containing heteroaryl (carbazole) [14].
PNG
media_image26.png
284
475
media_image26.png
Greyscale
PNG
media_image27.png
338
592
media_image27.png
Greyscale
Therefore, given the general formula and teachings of Ahn, 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 terphenyl for phenyl because Ahn teaches the variable may suitably be selected as terphenyl, like C-16, or phenyl, like C-97. 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 host in the emitting materials layer of the organic light emitting device of Choi and possess the benefits taught by Ahn. See MPEP 2143.I.(B).
Device 2 comprising the modified version of C-97 (hereafter “First Modified C-97”) reads on Applicant’s limitation since L1 and L2 are each unsubstituted parabiphenylene (shown below).
PNG
media_image28.png
365
412
media_image28.png
Greyscale
Regarding Claim 14, C-97 does not read on Applicant’s Formulae (111) to (114).
However, C-97 is represented by Ahn Formula (1) which does not specify the bonding between the two carbazole groups.
Given the general formula and teachings of Ahn, 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 C-97 wherein the two carbazoles are bonded meta to each other. 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 C-97 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as host in the emitting materials layer of the organic light emitting device of Choi and possess the properties taught by Ahn. 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.
Device 2 comprising the modified version of C-97 (hereafter “Second Modified C-97”) reads on Applicant’s limitation since Second Modified C-97 reads on Applicant’s Formula (114) (shown below),
PNG
media_image29.png
355
498
media_image29.png
Greyscale
PNG
media_image30.png
401
262
media_image30.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L1 is an unsubstituted arylene group having 12 ring carbon atoms (parabiphenylene) and L2 is a single bond,
R11 to R16 and R18 are each hydrogen,
R21 to R26 and R28 are each hydrogen,
X1 is a sulfur atom,
R31, R33 to R38 are each hydrogen,
R32 is bonded to *,
Regarding Claim 23, C-97 does not read on Applicant’s Formulae (121).
However, C-97 is represented by Ahn Formula (1) which does not specify the bonding position of the dibenzothiophene.
Given the general formula and teachings of Ahn, 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 C-97 wherein the dibenzothiophene is bonded in the meta position. 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 C-97 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as host in the emitting materials layer of the organic light emitting device of Choi and possess the properties taught by Ahn. 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.
Device 2 comprising the modified version of C-97 (hereafter “Third Modified C-97”) reads on Applicant’s limitation since Third Modified C-97 reads on Applicant’s Formula (121) (shown below),
PNG
media_image31.png
364
434
media_image31.png
Greyscale
PNG
media_image32.png
383
382
media_image32.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L1 is an unsubstituted arylene group having 12 ring carbon atoms (parabiphenylene) and L2 is a single bond,
R11 to R16 and R18 are each hydrogen,
R17 is bonded to *2,
R21 to R25 and R27 to R28 are each hydrogen,
R26 is bonded to *1,
X1 is a sulfur atom,
R31 to R33 and R35 to R38 are each hydrogen,
Regarding Claims 15–19, C-97 does not read on Applicant’s Formulae (115) to (119).
Ahn teaches C-113 [53]. Therefore, given the general formula and teachings of Ahn, 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 C-113 for C-97, because Ahn teaches the compounds may suitably be selected as a host material. 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 host in the emitting materials layer of the organic light emitting device of Choi and possess the benefits taught by Ahn. See MPEP 2143.I.(B).
Device 2 comprising C-113 reads on Applicant’s limitation since C-113 reads on Applicant’s Formula (119) (shown below),
PNG
media_image33.png
230
556
media_image33.png
Greyscale
PNG
media_image34.png
218
515
media_image34.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L1 is an arylene group having 6 ring carbon atoms (phenylene) substituted with an arylene group having 12 ring carbon atoms (naphthalene) and L2 is a single bond,
R11 to R14 and R-16 to R18 are each hydrogen,
R21 to R24 and R26 to R28 are each hydrogen,
X1 is a sulfur atom,
R32 to R38 are each hydrogen,
R31 is bonded to *.
Regarding Claims 24 and 34, Ahn does not teach an exemplified compound which reads on Applicant’s Formulae (131) to (134).
Ahn teaches C-113 [53]. C-113 is represented by Ahn Formula (1) which does not specify the bonding between the two carbazole groups.
Given the general formula and teachings of Ahn, 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 C-113 wherein the outside carbazole is bonded in the ortho position. 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 C-113 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as host in the emitting materials layer of the organic light emitting device of Choi and possess the properties taught by Ahn. 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.
Device 2 comprising the modified version of C-113 (hereafter “Modified C-113”) reads on Applicant’s limitation since Modified C-113 reads on Applicant’s Formula (131) (shown below),
PNG
media_image35.png
232
551
media_image35.png
Greyscale
PNG
media_image36.png
225
446
media_image36.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L1 is an arylene group having 6 ring carbon atoms (phenylene) substituted with an arylene group having 12 ring carbon atoms (naphthalene) and L2 is a single bond,
R11 to R14 and R-16 to R18 are each hydrogen,
R21 to R24 and R26 to R28 are each hydrogen,
X1 is a sulfur atom,
R32 to R38 are each hydrogen,
R31 is bonded to *.
Claims 1–9, 15–17, 19–21, 24–28, 30–35 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (US 2020/0127214 A1) in view of Hwang et al. (KR 20120122813 A, hereafter “Hwang”). An English translation was provided in this office action.
Regarding Claims 1–9, 15–17, 19–21, 24–28, 30–35, Choi teaches the organic light emitting diode of Example 1 including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emitting material layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode wherein the emitting material layer comprises TH-1, TD-1, and FD [0225]. TH-1 has a higher excited state singlet energy level than TD-1, and TD-1 has a higher excited state singlet energy level than FD [0010]. Choi further teaches Figure 4 which displays the energy relationship of TH-1 (Compound 1), TD-1 (Compound 2), and FD (Compound 3) (shown below). The energy relationship taught by Choi is very similar to the energy relationship taught by Applicant in Figure 5 of the instant application, wherein TH-1 corresponds to Compound M3, TD-1 corresponds to Compound M2, and FD corresponds to Compound M1 (shown below). Choi teaches TD-1 (corresponding to Applicant’s Compound M2) has the delayed fluorescent property [0114]. Additionally, Choi teaches TH-1 functions as a host in the emitting material layer [0025].
PNG
media_image1.png
555
576
media_image1.png
Greyscale
PNG
media_image2.png
392
588
media_image2.png
Greyscale
Hwang teaches compounds of Formula (1) which function as a host in an organic electroluminescent device [pg. 3 of English translation]. Hwang further teaches the compounds of Formula (1) have the advantage of being able to produce an organic light emitting device having high luminous efficiency and excellent lifetime characteristics [pg. 3 of English translation]. Specifically, Hwang teaches Compound 2 which is represented by Hwang’s Formula (1) (shown below) [pg. 6].
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 TH-1, taught by Choi, with Compound 2, taught by Hwang, based on the teaching of Hwang. The motivation for doing so would have been to produce a device having high luminous efficiency and excellent lifetime characteristics, as taught by Hwang.
PNG
media_image37.png
205
316
media_image37.png
Greyscale
PNG
media_image38.png
284
382
media_image38.png
Greyscale
However, Compound 2 does not read on Applicant’s Formulae (11) to (13) because the connection between carbazoles is in the para position instead of the meta position (shown with an arrow).
Therefore, given the general formula and teachings of Hwang, 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 2 wherein the carbazole bonding was changed from para to meta. One of ordinary skill in the pertinent art would have been motivated to produce additional positional isomers of the compound represented by Compound 2 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as host in the light emitting layer of the organic light emitting device of Hwang and possess the properties taught by Hwang. 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 organic light emitting device (hereafter “Device 3”) including an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emitting material layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode wherein the emitting material layer comprises the modified version of Compound 2 (hereafter “Modified Compound 2”), TD-1, and FD reads on Applicant’s limitation since TD-1 (corresponding to Applicant’s Compound M2) is a delayed fluorescent compound, and Modified Compound 2 (corresponding to Applicant’s Compound M3) reads on Applicant’s Formula (13) (shown below),
PNG
media_image39.png
213
525
media_image39.png
Greyscale
PNG
media_image40.png
183
432
media_image40.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
L1 is an unsubstituted arylene group having 12 ring carbon atoms (parabiphenylene) and L2 is a single bond,
R11 to R14 and R16 to R18 are each hydrogen,
R21 to R26 and R28 are each hydrogen,
R27 is bonded to *1,
X1 is a NR39,
R31 to R38 are each hydrogen,
R39 is not present since N is bonded to *,
Additionally, since Modified Compound 2 functions as a host material, as taught by Hwang, it is expected to have a high singlet energy. However, Hwang appears silent with respect to the singlet energy of Modified Compound 2 being higher than compound M2.
The instant specification recites that M3-3 may be used as compound M3 [0488].
PNG
media_image41.png
139
271
media_image41.png
Greyscale
PNG
media_image40.png
183
432
media_image40.png
Greyscale
Since Hwang teaches Modified Compound 2, an identical structure as disclosed by the Applicant, the property of singlet energy being higher than compound M2 is considered to be inherent (and would be expected to fall within the range in the claim), absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP 2112.
Therefore, Device 3 reads on Applicant’s Numerical Formula 1.
Per Claim 2, Device 3, as described above, also comprises FD, which corresponds to Applicant’s Compound M1. Choi teaches TD-1 (corresponding to Applicant’s Compound M2) has a higher excited state singlet energy level than FD (corresponding to Applicant’s Compound M1) [0010], reading on Applicant’s Numerical Formula 2.
Per Claim 3, Device 3 reads on Applicant’s limitation since no adjacent R11 to R18 are mutually bonded in Modified Compound 2.
Per Claim 4, Device 3 reads on Applicant’s limitation since no adjacent R21 to R28 are mutually bonded in Modified Compound 2.
Per Claim 5, Device 3 reads on Applicant’s limitation since no adjacent R31 to R38 are mutually bonded in Modified Compound 2.
Per Claims 6, 7, and 8, Device 3 reads on Applicant’s limitation since R11 to R14 and R16 to R18 are each hydrogen, R21 to R26 and R28 are each hydrogen, R31 to R38 are each hydrogen in Modified Compound 2. R39 is not present since X1 is N wherein the N is bonded to *.
Per Claim 9, Device 3 reads on Applicant’s limitation since L1 is an unsubstituted arylene group having 12 ring carbon atoms (parabiphenylene) and L2 is a single bond in Modified Compound 2.
Per Claims 15, 16, 17, Device 3 reads on Applicant’s limitation since Modified Compound 2 reads on Applicant’s Formula (117), wherein R11 to R18, R21 to R28, R31 to R39, X1, L1, L2, A2 are each the same as defined in Formula (13) above.
PNG
media_image42.png
258
560
media_image42.png
Greyscale
PNG
media_image40.png
183
432
media_image40.png
Greyscale
Per Claims 19 and 20, Device 3 reads on Applicant’s limitation since TD-1 (corresponding to Applicant’s Compound M2) reads on Applicant’s Formula (2) (shown below),
PNG
media_image10.png
214
238
media_image10.png
Greyscale
PNG
media_image11.png
359
261
media_image11.png
Greyscale
PNG
media_image12.png
210
305
media_image12.png
Greyscale
PNG
media_image13.png
174
138
media_image13.png
Greyscale
PNG
media_image14.png
131
139
media_image14.png
Greyscale
wherein:
n is 1,
m is 1,
q is 1,
CN is a cyano group,
D1 is represented by Formula (2b) wherein p is 2, A is represented by Formula (211) in once instance and Formula (212) in another instance (forming an indolocarbazole), R21 to R28, R2009, R2010 are each hydrogen, X201 is NR2013 wherein R2013 is an unsubstituted aryl group having 6 ring carbon atoms (phenyl),
RX is a heterocyclic group having 6 ring atoms (triazine) substituted with two aryl groups having 6 ring carbon atoms (phenyls).
Per Claim 21, Choi teaches the organic light emitting device of present disclosure may be applied to a display device and an illumination device [0025].
Per Claims 24, 27, 28, 34, Device 3 reads on Applicant’s limitation since Modified Compound 2 reads on Applicant’s Formula (131) (shown below),
PNG
media_image43.png
260
565
media_image43.png
Greyscale
PNG
media_image40.png
183
432
media_image40.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
Ar100 is an unsubstituted arylene group having 12 ring carbon atoms (parabiphenylene),
L2 is a single bond,
R11 to R14 and R16 to R18 are each hydrogen,
R21 to R26 and R28 are each hydrogen,
X1 is a NR39,
R31 to R38 are each hydrogen,
R39 is not present since N is bonded to *.
Per Claims 25, 30, 32, 35, Device 3 reads on Applicant’s limitation since Modified Compound 2 reads on Applicant’s Formula (143) (shown below),
PNG
media_image44.png
206
551
media_image44.png
Greyscale
PNG
media_image40.png
183
432
media_image40.png
Greyscale
wherein:
Ar2 is an aryl group having 6 carbon atoms (phenyl),
R100 is hydrogen,
n1 is 2
L2 is a single bond,
R11 to R14 and R16 to R18 are each hydrogen,
R21 to R26 and R28 are each hydrogen,
R27 is bonded to *1
X1 is a NR39,
R31 to R38 are each hydrogen,
R39 is not present since N is bonded to *.
Per Claim 26, 31, 33, Device 3 reads on Applicant’s limitation since Modified Compound 2 reads on Applicant’s Formula (143A) wherein R11 to R18, R21 to R28, R31 to R39, X1, L1, L2, A2 are each the same as defined in Formula (143) above, n1 is 2, and R100 is a hydrogen.
PNG
media_image45.png
181
551
media_image45.png
Greyscale
PNG
media_image40.png
183
432
media_image40.png
Greyscale
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Ueda et al. (US 2019/0088883 A1, hereafter “Ueda”) discloses compounds which read on Applicant’s Formula (13) of Applicant’s independent claim 1, such as I-85 [pg. 29] (shown below).
PNG
media_image46.png
421
179
media_image46.png
Greyscale
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.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/J.R.F./Examiner, Art Unit 1789
/MARLA D MCCONNELL/Supervisory Patent Examiner, Art Unit 1789
Prosecution Insights