DETAILED ACTION
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. KR10-2022-0081145, filed on 07/01/2022.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 05/24/2023 was filed after the mailing date of the instant application on 05/24/2023. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Response to Amendment
In the preliminary amendment filed 06/25/2026, the specification was amended.
These amendments are hereby entered.
Claims 1-24 are original and are examined herein.
Specification
The disclosure is objected to because of the following informalities:
The letters, numbers, and/or bonds in the chemical structure given in paragraphs [00219], [00220], and [00221] are illegible due to poor resolution. Please correct these structures so all letters, numbers, and/or bonds are clearly visible. See the example below.
PNG
media_image1.png
316
428
media_image1.png
Greyscale
Please note that this example is non-limiting and there may be other structures that require correction. Please check all formulae to make sure they are clear. Applicant may wish to make these structures clearer by increasing the size of the structure and/or font, or by making the bond lines thicker.
Appropriate correction is required.
Claim Rejections - 35 USC § 103
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.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1, 3-13, and 15-24 are rejected under 35 U.S.C. 103 as being unpatentable over Wu et al. (CN 111574543 A, using the provided translation for references), and further in view of Kuwabara et al. (US 2021/0175423 A1).
With respect to claims 1 and 5 Wu discloses an organic electroluminescent device comprising a first electrode (an anode, ITO), a second electrode facing the first electrode (a cathode, Al), and at least one functional layer between the electrodes (a light-emitting layer), and the light emitting layer comprises the boron-containing thermally activated delayed fluorescent (TADF) compound H-2, as well as host materials GH-1 and GH-2 (paragraph 0142), which are pictured below (pages 55 and 33 of the untranslated document).
PNG
media_image2.png
236
680
media_image2.png
Greyscale
PNG
media_image3.png
200
404
media_image3.png
Greyscale
Compound GH-2 meets the requirements of instant Formula HT when L1 is an unsubstituted C6 arylene group having 6 ring-forming carbon atoms (phenylene), Ar1 is an unsubstituted aryl groups having 6 ring-forming carbon atoms (phenyl), Y is a direct linkage, Z is C(Rz) wherein Rz is a hydrogen atom, Ry1 to Ry4 are not present, n31 is 0 so that R31 is not present, n32 is 1, and R32 is a substituted heteroaryl (carbazolyl) group having 12 ring-forming carbon atoms.
Compound GH-1 meets the requirements of instant Formula ET when Z1 to Z3 are nitrogen atoms, R35 and R33 are an unsubstituted C6 aryl group (phenyl), and R34 is a phenyl-substituted C18 heteroaryl (indolocarbazole) group.
Wu teaches additional examples of boron-containing TADF compounds suitable for use in the emissive layer of an organic light emitting device, which include Compound H205 (page 44 of the untranslated document), which is pictured below.
PNG
media_image4.png
296
686
media_image4.png
Greyscale
Compound H205 is derived from formula III-3 (page 27 of the untranslated document) which is pictured below.
PNG
media_image5.png
600
670
media_image5.png
Greyscale
In this formula, Wu teaches that Y7, Y10,Y12 and Y13 are each CR7 wherein R7 is a hydrogen atom (paragraph 0043, lines 1-3), h is 0 and g is 1 (paragraph 0015, lines 3-4), so that R4 is not present, and R3 is L-Ar, wherein L is a C5 heteroaryl group (m-pyridine) (paragraph 0020, lines 1-4), and Ar is a structure of general formula (2) (paragraph 0021 and page 26 of the untranslated document), such as the benzofurano[2,3-a]carbazole of the parent structure pictured above.
Such a modification produces a compound which meets the requirements of instant Formula 1 when X1 is an oxygen atom, X2 is N(R12) wherein R12 is a C6 aryl (phenyl) group, R1 through R5, R7, R8, R10 and R11 are all hydrogen atoms, R6 is represented by Formula 2, and R9 is a benzofurano[2,3-a]carbazole. In Formula 2, R16 and R17 are joined to form a fused benzofuran moiety, and all other R groups are hydrogen atoms.
Wu includes each element claimed, with the only difference between the claimed invention and Wu being a lack of the aforementioned selections being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent or bonding pattern from each of the finite lists of possible substituents and bonding patterns to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a TADF compound which has high glass transition temperature and molecular thermal stability, as well as suitable HOMO and LUMO energy levels for use as a host or dopant in the luminescent layer of an electroluminescent device with improved luminous efficiency and lifespan (paragraph 0012), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Wu does not teach nor fairly suggest the substituent L-Ar should be located at a position analogous to instant R6 and/or R9.
In analogous art, Kuwabara teaches an organic electroluminescent device comprising a boron-containing compound in the emission layer (abstract) and the boron-containing compound is substituted at at least one of two positions which are analogous to instant R6 and R9 (paragraph 0015 and Formula 1).
Kuwabara teaches that when a substituent capable of improving molecular durability is introduced at a location analogous to instant R6 and/or R9, the thermal stability of the polycyclic compound is improved, resulting in a device with improved external quantum efficiency (paragraph 0192).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to preferentially position the m-pyridinylene benzofurano[2,3-a]carbazole substituent at instant R6 and/or R9 in order to improve the thermal stability of the compound and obtain an organic electroluminescent device with improved external quantum efficiency, as taught by Kuwabara.
With respect to claims 3 and 4, Wu and Kuwabara teach the device of claim 1, and the first compound is represented by Formula 1-1a when R9a is benzofurano[2,3-a]carbazole (substituted carbazole) and all other R groups are hydrogen atoms, as pictured above.
With respect to claims 6 and 7, Wu and Kuwabara teach the device of claim 1, and the first compound is represented by Formula (1-2b) (claim 6) and Formula (1-3b) (claim 7) when R12b is an unsubstituted (Ry is hydrogen) C6 aryl (phenyl) group, as discussed above.
With respect to claims 8 and 9, Wu and Kuwabara teach the device of claim 1, and Formula 2 is represented by instant Formula 2-3 when Yb is an oxygen atom, n4 is 0, and all R groups are hydrogen atoms, as pictured above.
With respect to claim 10, Wu and Kuwabara teach the device of claim 1, as discussed above.
Wu also teaches that R1 and R2 are each a C4 alkyl (t-butyl) group (see for example Compound H54, page 35), h2 is 2 and R4 is a C6 aryl (phenyl) group, and Ar may be a benzo[3,2-b]carbazole group (see for example Compound H26, page 34).
Such a modification produces instant compound 49.
Wu includes each element claimed, with the only difference between the claimed invention and Wu being a lack of the aforementioned selections being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent or bonding pattern from each of the finite lists of possible substituents and bonding patterns to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a TADF compound which has high glass transition temperature and molecular thermal stability, as well as suitable HOMO and LUMO energy levels for use as a host or dopant in the luminescent layer of an electroluminescent device with improved luminous efficiency and lifespan (paragraph 0012), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claims 11 through 13, Wu and Kuwabara teach the device of claim 1, and Wu also teaches that the device comprises a hole transport layer, a light-emitting layer, and a electron transport layer, in that order (paragraph 0071 and Figure 1), and that the first, second, and third compound are in the emission layer and the emissive layer emits thermally activated delayed fluorescence, as discussed above.
With respect to claim 15, Wu discloses an organic electroluminescent device comprising a first electrode (an anode), a second electrode facing the first electrode (a cathode), and at least one functional layer between the electrodes (a light-emitting layer) (paragraph 0071 and Figure 1), and the light emitting layer comprises a boron-containing thermally activated delayed fluorescent (TADF) compound (paragraph 0061), such as compound Compound H205 (page 44 of the untranslated document), which is pictured below.
PNG
media_image4.png
296
686
media_image4.png
Greyscale
Compound H205 is derived from formula III-3 (page 27 of the untranslated document) which is pictured below.
PNG
media_image5.png
600
670
media_image5.png
Greyscale
In this formula, Wu also teaches that Y7, Y10,Y12 and Y13 are each CR7 wherein R7 is a hydrogen atom (paragraph 0043, lines 1-3), h is 0 and g is 1 (paragraph 0015, lines 3-4), so that R4 is not present, and R3 is L-Ar, wherein L is a C5 heteroaryl group (m-pyridine) (paragraph 0020, lines 1-4), and Ar is a structure of general formula (2) (paragraph 0021 and page 26 of the untranslated document), such as the benzofurano[2,3-a]carbazole of the parent structure pictured above.
Such a modification produces a compound which meets the requirements of instant Formula 1 when X1 is an oxygen atom, X2 is N(R12) wherein R12 is a C6 aryl (phenyl) group, R1 through R5, R7, R8, R10 and R11 are all hydrogen atoms, R6 is represented by Formula 2, and R9 is a benzofurano[2,3-a]carbazole. In Formula 2, R16 and R17 are joined to form a fused benzofuran moiety, and all other R groups are hydrogen atoms.
Wu includes each element claimed, with the only difference between the claimed invention and Wu being a lack of the aforementioned selections being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent or bonding pattern from each of the finite lists of possible substituents and bonding patterns to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a TADF compound which has high glass transition temperature and molecular thermal stability, as well as suitable HOMO and LUMO energy levels for use as a host or dopant in the luminescent layer of an electroluminescent device with improved luminous efficiency and lifespan (paragraph 0012), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Wu does not teach nor fairly suggest the substituent L-Ar should be located at a position analogous to instant R6 and/or R9.
In analogous art, Kuwabara teaches an organic electroluminescent device comprising a boron-containing compound in the emission layer (abstract) and the boron-containing compound is substituted at at least one of two positions which are analogous to instant R6 and R9 (paragraph 0015 and Formula 1).
Kuwabara teaches that when a substituent capable of improving molecular durability is introduced at a location analogous to instant R6 and/or R9, the thermal stability of the polycyclic compound is improved, resulting in a device with improved external quantum efficiency (paragraph 0192).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to preferentially position the m-pyridinylene benzofurano[2,3-a]carbazole substituent at instant R6 and/or R9 in order to improve the thermal stability of the compound and obtain an organic electroluminescent device with improved external quantum efficiency, as taught by Kuwabara.
With respect to claim 16, Wu and Kuwabara teach the device of claim 15, and the compound is represented by Formula 1-1a when R9a is benzofurano[2,3-a]carbazole and all other R groups are hydrogen atoms, as pictured above.
With respect to claim 17, Wu and Kuwabara teach the device of claim 15, and Formula 2 is represented by instant Formula 2-3 when Yb is an oxygen atom, n4 is 0, and all R groups are hydrogen atoms, as pictured above.
With respect to claim 18, Wu discloses Compound H205 (page 44 of the untranslated document), which is pictured below.
PNG
media_image4.png
296
686
media_image4.png
Greyscale
Compound H205 is derived from formula III-3 (page 27 of the untranslated document) which is pictured below.
PNG
media_image5.png
600
670
media_image5.png
Greyscale
In this formula, Wu also teaches that Y7, Y10,Y12 and Y13 are each CR7 wherein R7 is a hydrogen atom (paragraph 0043, lines 1-3), h is 0 and g is 1 (paragraph 0015, lines 3-4), so that R4 is not present, and R3 is L-Ar, wherein L is a C5 heteroaryl group (m-pyridine) (paragraph 0020, lines 1-4), and Ar is a structure of general formula (2) (paragraph 0021 and page 26 of the untranslated document), such as the benzofurano[2,3-a]carbazole of the parent structure pictured above.
Such a modification produces a compound which meets the requirements of instant Formula 1 when X1 is an oxygen atom, X2 is N(R12) wherein R12 is a C6 aryl (phenyl) group, R1 through R5, R7, R8, R10 and R11 are all hydrogen atoms, R6 is represented by Formula 2, and R9 is a benzofurano[2,3-a]carbazole. In Formula 2, R16 and R17 are joined to form a fused benzofuran moiety, and all other R groups are hydrogen atoms.
Wu includes each element claimed, with the only difference between the claimed invention and Wu being a lack of the aforementioned selections being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent or bonding pattern from each of the finite lists of possible substituents and bonding patterns to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a TADF compound which has high glass transition temperature and molecular thermal stability, as well as suitable HOMO and LUMO energy levels for use as a host or dopant in the luminescent layer of an electroluminescent device with improved luminous efficiency and lifespan (paragraph 0012), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Wu does not teach nor fairly suggest the substituent L-Ar should be located at a position analogous to instant R6 and/or R9.
In analogous art, Kuwabara teaches an organic electroluminescent device comprising a boron-containing compound in the emission layer (abstract) and the boron-containing compound is substituted at at least one of two positions which are analogous to instant R6 and R9 (paragraph 0015 and Formula 1).
Kuwabara teaches that when a substituent capable of improving molecular durability is introduced at a location analogous to instant R6 and/or R9, the thermal stability of the polycyclic compound is improved, resulting in a device with improved external quantum efficiency (paragraph 0192).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to preferentially position the m-pyridinylene benzofurano[2,3-a]carbazole substituent at instant R6 and/or R9 in order to improve the thermal stability of the compound and obtain an organic electroluminescent device with improved external quantum efficiency, as taught by Kuwabara.
With respect to claims 19 and 20, Wu and Kuwabara teach the compound of claim 18, and the compound is represented by Formula 1-1a when R9a is benzofurano[2,3-a]carbazole (substituted carbazole), R12 is a phenyl group, and all other R groups are hydrogen atoms, as pictured above.
With respect to claim 21, Wu and Kuwabara teach the compound of claim 18, and the first compound is represented by Formula (1-2b) when R12b is an unsubstituted C6 aryl (phenyl) group, as discussed above.
With respect to claims 22 and 23, Wu and Kuwabara teach the compound of claim 18, and Formula 2 is represented by instant Formula 2-3 when Yb is an oxygen atom, n4 is 0, and all R groups are hydrogen atoms, as pictured above.
With respect to claim 24, Wu and Kuwabara teach the compound of claim 18, as discussed above.
Wu also teaches that R1 and R2 are each a C4 alkyl (t-butyl) group (see for example Compound H54, page 35), h2 is 2 and R4 is a C6 aryl (phenyl) group, and Ar may be a benzo[3,2-b]carbazole group (see for example Compound H26, page 34).
Such a modification produces instant compound 49.
Wu includes each element claimed, with the only difference between the claimed invention and Wu being a lack of the aforementioned selections being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent or bonding pattern from each of the finite lists of possible substituents and bonding patterns to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a TADF compound which has high glass transition temperature and molecular thermal stability, as well as suitable HOMO and LUMO energy levels for use as a host or dopant in the luminescent layer of an electroluminescent device with improved luminous efficiency and lifespan (paragraph 0012), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Claims 2 and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Wu et al. (CN 111574543 A, using the provided translation for references) and Kuwabara et al. (US 2021/0175423 A1) as applied above, and further in view of Yoon et al. (US 2020/0308209 A1).
With respect to claim 2, Wu and Kuwabara teach the device of claim 1, as discussed above.
However, neither Wu nor Kuwabara teach nor fairly suggest that the functional layer further comprises a fourth compound of instant Formula PS.
In analogous art, Yoon teaches an organic light emitting device comprising an emission layer and the emission layer comprises a first and second dopant, wherein the first dopant is a platinum, organometallic compound and the second dopant is a boron-containing TADF (paragraph 0384) compound (abstract and paragraphs 0309 and 0383).
Yoon teaches that when the first and second dopant both participate in emission, the luminescence efficiency is improved. Further, after excitons are transferred to the first dopant, excitons may then transfer from the first dopant to the second dopant, therefore preventing or reducing deterioration of the second dopant due to the energy of the excitons, improving lifespan characteristics.
Yoon gives an example of a suitable first, organometallic dopant, Compound 40-2 (page 41), which is pictured below.
PNG
media_image6.png
354
450
media_image6.png
Greyscale
This compound meets the requirements of instant Formula PS when Q1 through Q3 are a carbon atom and Q4 is a nitrogen atom, C1 is a substituted C3 heteroaryl (imidazole-derived carbene), C2 and C3 are both a C6 hydrocarbon (benzene) ring, and C4 is a C5 heterocycle (pyridine), e1 through e3 are each 1, and e4 is 0 so that L14 is not present, L11 is a direct linkage, L12 is divalent oxygen, and L13 is trivalent nitrogen, wherein R47 is a C6 aryl group which is further bonded to C3 to form a carbazole moiety, d1 is 1 and R41 is a methyl-substituted C6 aryl (phenyl) group, d2 is 1 and R42 is a C4 (t-butyl) alkyl group, d3 is 0 and R43 is not present, and d4 is 1 and R44 is a C4 (t-butyl) alkyl group.
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to include a second, emissive dopant in the emissive layer of the device of Wu and Kuwabara in order to improve the luminescence efficiency, and prevent or reduce deterioration of the second dopant due to the energy of the excitons, resulting in improved lifespan characteristics, as taught by Yoon.
With respect to claim 14, Wu, Kuwabara and Yoon teach the device of claim 2, and the first, second, third, and fourth compound are all located in the emission layer, as discussed above.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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, 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.
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.
/RACHEL SIMBANA/Examiner, Art Unit 1786
Prosecution Insights