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 .
Priority
2. Acknowledgment is made of applicant's claim for foreign priority based on
applications filed in Korea on February 22, 2021 and February 21, 2022.
3. 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).
4. Failure to provide a certified translation may result in no benefit being accorded
for the non-English application.
Information Disclosure Statement
5. The references provided in the Information Disclosure Statements filed on June
13, 2023, July 1, 2024, September 6, 2024, and July 8, 2025 have been considered. Signed copies of the corresponding 1449 forms have been included with this office action.
Claim Rejections - 35 USC § 103
6. 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.
7. 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.
8. 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.
9. 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.
10. Claims 1-5 and 7-12 are rejected under 35 U.S.C. 103 as being unpatentable over Yun et al (WO 2020/101169 A1; English machine translation obtained from WIPO, hereinafter “Yun”).
11. Regarding claims 1-5 and 7-12, Yun teaches compounds for organic light emitting devices (¶ [0001]) represented by Chemical Formula 1 (Yun) (¶ [0049]-[0064], see below) wherein:
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12. Yun teaches that organic light emitting devices comprising compounds of Chemical Formula 1 (Yun) in an organic material layer exhibit lower driving voltages and improved luminous efficiency (¶ [0008]) and that the organic material layer can be the light emitting layer wherein the compounds represented by Chemical Formula 1 (Yun) can be the host material therein (¶ [0297]-[0303]).
13. Yun discloses the following compound P 1-9 (¶ [0078], see structure below) which fails to read on all of the limitations of Chemical Formula 1 of claim 1 due to a difference in the bonding position of the triazine moiety with the dibenzofuran (X = O) or dibenzothiophene (X = S) group (see the circled carbon below for the bonding position that would render compound P 1-9 to read on claim 1). However, as shown by the structure of Chemical Formula 1 (Yun) above, the bonding position of the triazine moiety to the dibenzofuran group is variable (¶ [0050]).
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14. Given the general formula and teachings of Yun, 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 P 1-9 (Yun) wherein the triazinyl moiety is transposed to the carbon atom circled (see above). One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Yun’s Chemical Formula 1/the positional isomers of the compound represented by compound P 1-9 (Yun) 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 material in the light emitting layer of the organic light emitting device of Yun and possess the properties taught by Yun (lower driving voltages and improved luminous efficiency, ¶ [0008]). 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.
15. The modified positional isomer of P 1-9 (Yun) is shown below.
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16. Per claim 1, the compound Modified P 1-9 (Yun) reads on all of the limitation of Chemical Formula 1 of the instant application wherein:
Y is oxygen; and
D is deuterium; and
L is a single bond; and
L1 and L2 are single bonds; and
Ar1 is an unsubstituted C10 aryl group and Ar2 is an unsubstituted C18 heteroaryl group containing a nitrogen atom; and
R is a hydrogen atom.
17. Per claim 2, the compound Modified P 1-9 (Yun) reads on the limitation wherein L is a single bond.
18. Per claim 3, the compound Modified P 1-9 (Yun) reads on all of the limitations wherein L1 and L2 are each independently single bonds.
19. Per claim 4, the compound Modified P 1-9 (Yun) reads on all of the limitations wherein:
Ar1 is an unsubstituted naphthyl group; and
Ar2 is an a carbazolyl group substituted with phenyl.
20. Per claim 5, the compound Modified P 1-9 (Yun) reads on all of the limitations wherein:
Ar1 is
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; and
Ar2 is
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21. Per claims 7 and 8, the compound Modified P 1-9 (Yun) reads on the limitation wherein R is a hydrogen atom.
22. Per claim 9, the compound Modified P 1-9 (Yun) reads on all the limitations of Chemical Formula 1-1 wherein:
Y, L1, L2, Ar1 and Ar2 are the same as previously defined.
23. Regarding claim 10, the compound Modified P 1-9 (Yun) fails to read on the limitation wherein it is selected from the one of the compounds enumerated.
24. Yun does teach, however, that in Chemical Formula 1 (Yun) (see below), Ar1 and Ar2 can be C6 to C60 aryl groups (¶ [0060]), and phenyl and naphthyl groups are preferred when Ar1 and/or Ar2 is an aryl group (¶ [0062]) and discloses compound P 1-13 wherein Ar1 is phenyl (¶ [0078]).
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25. Therefore, given the general formula and teachings of Yun, 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 Ar1 from naphthyl group to a phenyl group, as exemplified in compound P 1-13, because Yun teaches the variable Ar1 may preferably be selected as a phenyl group. 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 material in the light emitting layer of the organic light emitting device of Yun and possess the benefits taught by Yun. See MPEP 2143.I.(B).
26. The modification of compound Modified P 1-9 (Yun), wherein Ar1 is substituted from naphthyl to phenyl is depicted below.
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27. Per claim 10, the compound Modified P 1-9 (2) reads on the limitation wherein it is identical to the compound
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on pg. 8 of the instant claims.
28. Regarding claims 11-12, Yun teaches an organic light emitting device (¶ [0297]-[0303]) comprising:
a first electrode (ITO, ¶ [0298]); and
a second electrode disposed to face the first electrode (Al, ¶ [0301]); and
an organic material layer including one or more layers between the first electrode and the second electrode comprising a compound of Chemical Formula 1 (Yun) (¶ [0299]); and
the organic material layer comprising a compound of Chemical Formula 1 (Yun), as a host material, is a light emitting layer (¶ [0299]).
29. While Yun does not teach Modified P 1-9 (Yun) in an organic light emitting device, Yun does generally teach uses of compounds represented by Chemical Formula 1 (Yun) in organic light emitting devices of claim 11. At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to use the compound Modified P 1-9 (Yun) as the host material in a device having the structure taught by Yun above, because this 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 Yun (lower driving voltages and improved luminous efficiency, ¶ [0008]). See MPEP 2143(I)(A).
30. Per claims 11-12, the modified organic light emitting device of Yun comprising the compound Modified P 1-9 (Yun) in the light emitting organic material layer reads on all the limitations therein.
31. Claims 13-14 are rejected under 35 U.S.C. 103 as being unpatentable over Yun et al (WO 2020/101169 A1; English machine translation obtained from WIPO, hereinafter “Yun”), as applied to claim 12 above, and in further view of Tanaka et al. (US 2016/0268516 A1; hereinafter “Tanaka”).
32. Regarding claims 13-14, the modified organic light emitting device of Yun fails to teach a light emitting layer further comprising a compound represented by Chemical Formula 2 of the instant application, nor one of the enumerated examples.
33. Tanaka teaches organic light emitting devices comprising a compound represented by Formula (I) (Tanaka) (see below, ¶ [0027]-[0028]) as a host compound in the light emitting layer that exhibit high efficiency and long service lifetimes ([Abstract]).
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34. Tanaka teaches compounds of Formula (I) (Tanaka) are useful host materials in organic light emitting devices due to their high carrier transport ability, high glass transition temperature (Tg), and high triplet energy (T1) that is appropriate for emission of shorter wavelengths of light (¶ [0197]).
35. Tanaka also teaches that the charge transport characteristics of an organic light emitting device can be adjusted by use of a plurality of host materials in the light emitting layer to achieve high efficiency (¶ [0190]).
36. Tanaka specifically teaches the use of compound H-80 as a host material {¶ [0221]; see structure below, and Table 2-2, Element No. 1-83)} representing Formula (I) (Tanaka).
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37. 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 utilize compound H-80 as an additional host material in the modified organic light emitting device of Yun, based on the teaching of Tanaka. The motivation for doing so would have been to adjust the charge transport characteristics of the light emitting layer to achieve high efficiency and long service lifetimes, and to provide a host compound with high carrier transport ability, high glass transition temperature, and high triplet energy (¶ [0190]), as taught by Tanaka.
38. Per claim 13, modified organic light emitting device of Yun, as modified by Tanaka, comprising compound H-80 of Tanaka in the light emitting layer reads on all the limitations of Chemical Formula 2 wherein:
Ar’1 and Ar’2 are each unsubstituted C6 aryl groups; and
R’1 and R’2 are each hydrogen atoms; and
r and s are integers equal to seven.
39. Per claim 14, modified organic light emitting device of Yun, as modified by Tanaka, comprising compound H-80 of Tanaka in the light emitting layer reads on the limitation wherein it is identical to
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on pg. 27 of the instant claims.
40. Claims 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Cho et al (US 2019/0372012 A1; hereinafter “Cho”) in view of Li et al. (US 2002/0076576 A1; hereinafter “Li”) and Yun et al (WO 2020/101169 A1; English machine translation obtained from WIPO, hereinafter “Yun”).
41. Regarding claims 1-14, Cho teaches an organic light emitting device comprising a first host compound and a second host compound that exhibits improved driving voltage, efficiency, and lifetime ([Abstract]).
42. Cho teaches that the first host compound is represented by Chemical Formula 1 (Cho) (see below, ¶ [0011]-[0017]) wherein:
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43. Cho teaches that the second host compound is represented by Chemical Formula 2 (Cho) (see below, ¶ [0018]-[0023]) wherein:
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44. Cho teaches an organic light emitting device (¶ [0164]-[0167]) comprising:
a first electrode (ITO, ¶ [0165]); and
a second electrode disposed to face the first electrode (Al, ¶ [0165]); and
an organic material layer including one or more layers between the first electrode and the second electrode comprising a compound of Chemical Formula 1 (Cho) and a compound of Chemical Formula 2 (Cho) (¶ [0165]); and
the organic material layer comprising a compound of Chemical Formula 1 (Cho) and a compound of Chemical Formula 2 (Cho) is a light emitting layer (¶ [0165]).
45. Cho specifically discloses an organic light emitting device (see Table 1, Experimental Ex. 4) wherein the light emitting layer comprises compound 3 (Cho) representing Chemical Formula 1 (Cho) (see below, ¶ [0059], pg. 18, and ¶ [0106]-[0111]) and compound 2-4 (Cho) representing Chemical Formula 2 (Cho) (see below, ¶ [0068], pg. 25, and ¶ [0144]-[0146]).
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46. Regarding claim 1, compound 3 (Cho) fails to read on the limitations of Chemical Formula 1 of the instant application due to the absence of deuteration on the phenyl group indicated with a circle (see above).
47. Li teaches that carbon-deuterium bonds are stronger, more stable, and react more slowly than carbon-hydrogen bonds, which contributes to better thermal stability and longer organic light emitting device lifetimes (¶ [0009]).
48. Li fails to teach a specific site for deuterium incorporation, but does broadly teach the benefits of the carbon-deuterium bond.
49. Yun teaches compounds for organic light emitting devices (¶ [0001]) represented by Chemical Formula 1 (Yun) (¶ [0049]-[0064]).
50. Yun discloses the following compound P 1-9 (¶ [0078], see structure below) wherein the phenyl-D5 group is indicated with a circle.
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51. 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 the protio-phenyl group of compound 3 (Cho) in position 4 of the dibenzofuran with a deutero-phenyl group, as exemplified by Yun’s compound P 1-9, based on the teaching of Li and Yun. The motivation for doing so would have been to obtain deuterated organic semiconducting materials possessing the benefits as taught by Li (carbon-deuterium bonds are stronger, more stable, and react more slowly than carbon-hydrogen bonds, which contributes to better thermal stability and longer organic light emitting device lifetimes, ¶ [0009]).
52. The compound 3 (Cho), modified by Li and Yun, is depicted below.
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53. Per claim 1, compound 3 (Cho; Li and Yun Modifications) reads on all of the limitation of Chemical Formula 1 of the instant application wherein:
Y is oxygen; and
D is deuterium; and
L is a single bond; and
L1 and L2 are single bonds; and
Ar1 is an unsubstituted C12 aryl group and Ar2 is an unsubstituted C6 aryl group; and
R is a C6 aryl group substituted with deuterium.
54. Per claim 2, compound 3 (Cho; Li and Yun Modifications) reads on the limitation wherein L is a single bond.
55. Per claim 3, compound 3 (Cho; Li and Yun Modifications) reads on all of the limitations wherein L1 and L2 are each independently single bonds.
56. Per claim 4, compound 3 (Cho; Li and Yun Modifications) reads on all of the limitations wherein:
Ar1 is an unsubstituted biphenyl group; and
Ar2 is an unsubstituted phenyl group.
57. Per claim 5, compound 3 (Cho; Li and Yun Modifications) reads on all of the limitations wherein:
Ar1 is
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; and
Ar2 is
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.
58. Per claim 6, compound 3 (Cho; Li and Yun Modifications) reads on all of the limitations wherein:
Ar1 is an unsubstituted C12 group; and
Ar2 is an unsubstituted C6 group.
59. Per claims 7 and 8, compound 3 (Cho; Li and Yun Modifications) reads on the limitation wherein R is a phenyl group substituted with deuterium and R is identical to
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.
60. Per claim 9, compound 3 (Cho; Li and Yun Modifications) reads on all the limitations of Chemical Formula 1-3 wherein:
Y, L1, L2, Ar1 and Ar2 are the same as previously defined.
61. Per claim 10, compound 3 (Cho; Li and Yun Modifications) reads on the limitation wherein it is identical to the compound
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on pg. 11 of the instant claims.
62. Regarding claims 11-14, the modified organic light emitting device of Cho comprising compound 3 (Cho; Li and Yun Modifications) and compound 2-4 (Cho) in the light emitting organic material layer reads on all the limitations therein.
63. Per claim 13, the modified organic light emitting device of Cho comprising compound 3 (Cho; Li and Yun Modifications) and compound 2-4 (Cho) (see below) in the light emitting organic material layer reads on all the limitations of Chemical Formula 2 wherein:
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Ar’1 and Ar’2 are each unsubstituted C12 aryl groups; and
R’1 and R’2 are each hydrogen atoms; and
r and s are integers equal to seven.
64. Per claim 14, the modified organic light emitting device of Cho comprising compound 3 (Cho; Li and Yun Modifications) and compound 2-4 (Cho) (see below) in the light emitting organic material layer reads on the limitation wherein it is identical to
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on pg. 27 of the instant claims.
Conclusion
65. 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 7:30 AM - 5:00 PM.
66. 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.
67. 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.
68. 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.
/B.J.C./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786
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