DETAILED ACTION
Notice of Pre-AIA or AIA Status
1. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Specification
2. The abstract of the disclosure is objected to because it exceeds the maximum length of 150 words. A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
Claim Rejections - 35 USC § 102
3. In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
4. 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.
5. Claims 1-4, 6-7, and 9-10 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kim et al. (KR 10-2020-0046229 A, using US 2021/0380568 A1 as the official English language translation).
6. Regarding claim 1, Kim teaches the polycyclic compound P-20 (structure shown below, ¶ [0087]).
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7. Compound P-20 reads on Chemical Formula 1 wherein:
Y is an oxygen atom; and
A is a naphthalene ring; and
L1 and L2 are each independently direct bonds; and
Ar1, Ar2, Ar3 are unsubstituted phenyls and Ar4 is a substituted dibenzothiophene; and
R1 are each independently hydrogen atoms; and
m is equal to zero
8. Regarding claim 2, Kim teaches the polycyclic compound P-20 (see Regarding claim 1 above for structure).
9. Compound P-20 reads on Chemical Formula 1-2 wherein:
the naphthalene ring A is linearly fused to form a benzo[b]naphtho[2,3-d]furan; and
Y, L1, L2, Ar1, Ar2, Ar3, Ar4, R1, and m are the same as previously defined.
10. Regarding claim 3, Kim teaches the polycyclic compound P-20 (see Regarding claim 1 above for structure).
11. Compound P-20 reads on Chemical Formula 2-6 wherein:
the diaryl amino substituents are disposed in a 1,4-relationship; and
Y, L1, L2, Ar1, Ar2, Ar3, Ar4, R1, and m are the same as previously defined.
12. Regarding claim 4, Kim teaches the polycyclic compound P-20 (see Regarding claim 1 above for structure).
13. Compound P-20 reads on claim 4 wherein:
L1 and L2 are each independently direct bonds.
14. Regarding claim 6, Kim teaches the polycyclic compound P-20 (see Regarding claim 1 above for structure).
15. Compound P-20 reads on claim 6 wherein:
R1 is each independently hydrogen atoms.
16. Regarding claim 7, Kim teaches the polycyclic compound P-20 (see Regarding claim 1 above for structure).
17. Compound P-20 reads on claim 7 wherein:
m is equal to zero.
18. Regarding claim 9, Kim teaches an organic light emitting device comprising:
a first electrode (ITO, ¶ [0178]); and
a second electrode opposite the first electrode (Al, ¶ [0178]); and
one or more organic material layers between the first and second electrodes, wherein one or more layers of the organic material layers comprises compound P-20 (auxiliary emission layer, ¶ [0178], see also Example 21 (Table 7)).
19. Regarding claim 10, Kim teaches an organic light emitting device wherein compound P-20 is included in one or more organic material layers and the organic material layer is a light emitting layer (auxiliary emission layer, ¶ [0178], see also Example 21 (Table 7)).
Claim Rejections - 35 USC § 103
20. In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
21. 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.
22. 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.
23. 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.
24. Claims 1-4 and 6-10 are rejected under 35 U.S.C. 103 as being unpatentable over Ikeda et al. (US 2014/0183500 A1).
25. Regarding claims 1-4 and 6-8, Ikeda teaches amine compounds having fused polycyclic furan and thiophene moieties (¶ [0011]) represented by Formula 1 (¶ [0012], shown below) wherein:
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n is an integer of 1 to 4 (¶ [0014], and preferably n = 2 (¶ [0033])); and
A is represented by Formula 4 (¶ [0016]; Formula 4 depicted ¶ [0022]); and
B is represented preferably by Formula 13 (¶ [0050]).
26. The moiety A represented by Formula 4 (shown below, ¶ [0022]) is defined as follows wherein:
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Ar1 and Ar2 are independently substituted or unsubstituted aryl groups or heteroaryl groups (¶ [0023]); and
L, L1, and L2 are single bonds, arylenes, or heteroarylenes (¶ [0024]).
27. The moiety B represented by Formula 13 (shown below, ¶ [0050]) is defined as follows wherein:
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X is an oxygen atom or a sulfur atom (¶ [0038]); and
R1-R6 and R31-R34 each independently represent a bond to moiety A, where more preferably two of the ten possible positions represent a direct bond to moiety A (¶ [0050]).
28. Ikeda does not teach an exemplified compound that meets all of the limitations of Chemical Formula 1 as per claim 1, however Ikeda does disclose the following compound (¶ [0074], pg. 84, see below).
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29. The compound of Ikeda (shown above) meets all of the limitations of claim 1, but fails to include a second diaryl amino substituent on the benzo-portion of the polycycle (positions R1, R2, and R4 as per Formula 13). However, as shown by Formula 13, Ikeda teaches that these positions may be substituted with moiety A, and more preferably two positions represent a direct bond to moiety A (¶ [0050]).
30. Therefore, given Formula 13 and teachings of Ikeda, 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 hydrogen atom of position R1 on the compound of Ikeda with a diphenyl amino substituent, because Ikeda teaches this variable may be preferably selected as moiety A. This substitution is depicted below with Compound Ikeda (Modified).
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31. 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 dopant material in the fluorescent emitting layer of an organic electroluminescent device of Ikeda (¶ [0075]) and possess the benefits taught by Ikeda (high emission efficiency at a low driving voltage (¶ [0225])). See MPEP 2143.I.(B).
32. Regarding claim 1, Compound Ikeda (Modified) reads on Chemical Formula 1 wherein:
Y is an oxygen atom; and
A is a naphthalene ring; and
L1 and L2 are each independently direct bonds; and
Ar1, Ar2, Ar3, and Ar4 are unsubstituted phenyls; and
R1 are each independently hydrogen atoms; and
m is equal to zero.
33. Regarding claim 2, Compound Ikeda (Modified) reads on Chemical Formula 1-3 wherein:
the naphthalene ring A is angularly fused to form a benzo[b]naphtho[1,2-d]furan; and
Y, L1, L2, Ar1, Ar2, Ar3, Ar4, R1, and m are the same as previously defined.
34. Regarding claim 3, Compound Ikeda (Modified) reads on Chemical Formula 2-5 wherein:
the diaryl amino substituents are disposed in a 1,3-relationship; and
Y, L1, L2, Ar1, Ar2, Ar3, Ar4, R1, and m are the same as previously defined.
35. Regarding claim 4, Compound Ikeda (Modified) reads on claim 4 wherein:
L1 and L2 are each independently direct bonds.
36. Regarding claim 6, Compound Ikeda (Modified) reads on claim 6 wherein:
R1 is each independently hydrogen atoms.
37. Regarding claim 7, Compound Ikeda (Modified) reads on claim 7 wherein:
m is equal to zero.
38. Regarding claim 8, Compound Ikeda (Modified) reads on claim 8 wherein it is identical to one of the exemplified compounds representing Chemical Formula 1 (see pg. 9 of Claims).
39. Regarding claims 9 and 10, Ikeda teaches organic light emitting devices comprising:
a first electrode (ITO, ¶ [0214]); and
a second electrode opposite the first electrode (Al, ¶ [0222]); and
one or more organic material layers between the first and second electrodes, wherein one or more layers of the organic material layers comprises amine compounds having fused polycyclic furan and thiophene moieties represented by Formula 1 (Ikeda) (¶ [0218]); and
the amine compounds having fused polycyclic furan and thiophene moieties represented by Formula 1 (Ikeda) are included in a light emitting layer (¶ [0218]).
40. While Ikeda does not teach Compound Ikeda (Modified) in an organic light emitting device, Ikeda does generally teach uses of amine compounds having fused polycyclic furan and thiophene moieties represented by Formula 1 in organic light emitting devices of claim 9. At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the organic light emitting devices of Ikeda by using the Compound Ikeda (Modified) as the fluorescence emitting dopant of the emission layer, based on the teaching of Ikeda. The modification would have been a combination of prior art elements according to known methods to yield predictable results and one of ordinary skill in the art would reasonably expect the modified organic light emitting devices to possess the benefits taught by Ikeda (high emission efficiency at a low driving voltage (¶ [0225])). See MPEP 2143(I)(A).
41. The modified organic light emitting device of Ikeda comprising Compound Ikeda
(Modified) in the light emitting organic material layer reads on all the limitations of claims 9 and 10.
42. Claims 1-7 and 9-10 are rejected under 35 U.S.C. 103 as being unpatentable over Mun et al. (KR 10-2019-0072816 A, English translation obtained from Global Dossier).
43. Regarding claims 1-7, Mun teaches polycyclic dibenzofuran- and dibenzothiophene-containing compounds represented by Chemical Formula 1 (¶ [0009]-[0010], shown below) wherein:
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X is an oxygen or sulfur atom (¶ [0038]); and
R1 and R2 can each independently be L-N(Ra)(Rb) (¶ [0039]); and
L can be a direct bond (¶ [0043]); and
Ra and Rb can each independently be aryl or heteroaryl groups (¶ [0045]); and
adjacent R1 and R2 substituents can form additional carbocyclic rings (¶ [0039]).
44. Mun does not teach an exemplified compound that meets all of the limitations of Chemical Formula 1 as per claim 1, however Mun does disclose the following compound (¶ [0123], see below).
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45. Compound 2-56 (Mun), shown above, meets all of the limitations of claim 1, but fails to include ring A as a naphthalene ring. However, as shown by Chemical Formula 1 (Mun), Mun teaches that adjacent substituents can be present to form additional carbocyclic rings (¶ [0039]).
46. Additionally, Mun discloses the following compound 1-42’ (¶ [0116], see below) wherein the diaryl amino substituted-dibenzofuran framework is annealed with an additional benzo-moiety (circled below), forming a benzo[b]naphtho[1,2-d]furan framework.
[AltContent: oval]
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47. Therefore, given Chemical Formula 1 (Mun), the teachings of Mun, and the disclosure of Compound 1-42’, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to anneal an additional benzo-moiety on Compound 2-56 of Mun, because Mun teaches adjacent substituents on the dibenzofuran framework may form additional carbocyclic rings and that the benzo[b]naphtho[1,2-d]furan framework is a preferred heterocyclic scaffold. This modification is depicted below with Compound 2-56 (Modified).
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48. 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 luminescent material in the light emitting layer of an organic electroluminescent device of Mun (¶ [0202]) and possess the benefits taught by Mun (high luminous efficiency, low driving voltage, high heat resistance, improved color purity, and improved lifespan [Abstract]). See MPEP 2143.I.(B).
49. Regarding claim 1, Compound 2-56 (Modified) reads on Chemical Formula 1 wherein:
Y is an oxygen atom; and
A is a naphthalene ring; and
L1 and L2 are each independently direct bonds; and
Ar1 and Ar3 are biphenyls, and Ar2 and Ar4 are dibenzothiophenyl; and
R1 are each independently hydrogen atoms; and
m is equal to zero.
50. Regarding claim 2, Compound 2-56 (Modified) reads on Chemical Formula 1-3 wherein:
the naphthalene ring A is angularly fused to form a benzo[b]naphtho[1,2-d]furan; and
Y, L1, L2, Ar1, Ar2, Ar3, Ar4, R1, and m are the same as previously defined.
51. Regarding claim 3, Compound 2-56 (Modified) reads on Chemical Formula 2-4 wherein:
the diaryl amino substituents are disposed in a 1,3-relationship; and
Y, L1, L2, Ar1, Ar2, Ar3, Ar4, R1, and m are the same as previously defined.
52. Regarding claim 4, Compound 2-56 (Modified) reads on claim 4 wherein:
L1 and L2 are each independently direct bonds.
53. Regarding claim 5, Compound 2-56 (Modified) reads on claim 5 wherein:
Ar1 and Ar3 are biphenyls, and Ar2 and Ar4 are dibenzothiophenyl.
54. Regarding claim 6, Compound 2-56 (Modified) reads on claim 6 wherein:
R1 is each independently hydrogen atoms.
55. Regarding claim 7, Compound 2-56 (Modified) reads on claim 7 wherein:
m is equal to zero.
56. Regarding claims 9 and 10, Mun teaches organic light emitting devices comprising:
a first electrode (ITO, ¶ [0201]); and
a second electrode opposite the first electrode (Al, ¶ [0205]); and
one or more organic material layers between the first and second electrodes, wherein one or more layers of the organic material layers comprises polycyclic dibenzofuran- and dibenzothiophene-containing compounds (¶ [0202]); and
the polycyclic dibenzofuran- and dibenzothiophene-containing compounds are included in a light emitting layer (auxiliary emission layer, ¶ [0202]).
57. While Mun does not teach Compound 2-56 (Modified) in an organic light emitting device, Mun does generally teach uses of polycyclic dibenzofuran- and dibenzothiophene-containing compounds in organic light emitting devices of claim 9. At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the organic light emitting devices of Mun by using the Compound 2-56 (Modified) as an organic light emitting material of the emission layer, based on the teaching of Mun. The modification would have been a combination of prior art elements according to known methods to yield predictable results and one of ordinary skill in the art would reasonably expect the modified organic light emitting devices to possess the benefits taught by Mun (high luminous efficiency, low driving voltage, high heat resistance, improved color purity, and improved lifespan [Abstract]). See MPEP 2143(I)(A).
58. The modified organic light emitting device of Mun comprising Compound 2-56 (Modified) in the light emitting organic material layer reads on all the limitations of claims 9 and 10.
Conclusion
59. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Brandon J. Cooper whose telephone number is (571)272-0005. The examiner can normally be reached Monday - Friday 8:30 AM - 5:00 PM.
60. 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.
61. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached at (571) 272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/B.J.C./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786