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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 03/11/2026 has been entered.
This office action is in response to the amendment filed 03/11/2026, which amends claims 1, 6, 14, 15, 16, and 20 and cancels claims 7, 9, 10, 12, 13, 23, and 25. Claims 1-6, 8, 11, 14-22, and 24 are pending in the application.
Response to Amendment
In the response filed 03/11/2026, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 112(b) of claim 23 as failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention, and the rejections under 35 U.S.C. 103 of claims 1-6, 8, 11, 17, and 21-25 as being unpatentable over Choi et al. (WO 2019/240462 A1), claims 18 and 19 as being unpatentable over Choi above and further in view of Hatakeyama et al. (US 2018/0069182 A1), claim 20 as being unpatentable over Choi above, and further in view of Xia et al. (US 2015/0214494 A1), and of claims 1-2, 4-6, 8, 11, 17, and 20 as being unpatentable over Kim et al. (US 2020/0098991 A1) are withdrawn by the Office.
Response to Arguments
Applicant's arguments filed 03/11/2026 have been fully considered but they are not persuasive.
With respect to Applicant’s argument that neither Choi nor Kim provide for a compound wherein not all of L1, L2, and L3 are the same, and when L3 is not present, then L1 and L2 are different, Examiner disagrees.
Choi lists the definitions for Y1 and Y2 separately (paragraph 24) and demonstrates several formulae with different definitions for L groups, such as Chemical Formulae 4-8 and 4-9 (paragraphs 200-203). Kim also lists definitions for Y1 and Y2 separately (paragraph 0011 and 0012). Additionally, neither Choi nor Kim explicitly state that the positions analogous to instant L1 and L2 must be the same element.
It has been held that though a specific embodiment is not taught as preferred makes it no less obvious, also, that the mere fact that a reference suggests a multitude of possible combinations does not in and of itself make any one of those combinations less obvious (see Merck v. Biocraft, 10 USPQ2d 1843 (Fed Cir 1985), see also MPEP 2123). The prior art does not need to demonstrate a specific embodiment with two different elements at instant L1 and L2 for it to be within the scope of the prior art (see MPEP 2144.08).
In determining whether one of ordinary skill in the art would have had reason to select the claimed subgenus from the work of Choi and Kim, Examiner notes that the size of the genus is small. Choi teaches only two possible definitions for Y1 and Y2. Similarly, Kim teaches only 6 possible definitions for Y1 and 6 possible definitions for Y2. The size of this genus is not prohibitively large, particularly because the majority of these options satisfy the requirement of the claim. Further, while the prior art does not have any express teachings to select different elements at instant L1 and L2, the instant disclosure does not appear to have any express teaching as to why a person of ordinary skill in the art should select different elements at instant L1 and L2, and thus it is unclear whether such a selection has unexpected advantages over the prior art, or whether such a selection is arbitrary.
Applicant’s remaining arguments have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Claim Objections
Claim 20 is objected to because of the following informalities:
The word “compound” is repeated twice in a row in lines 6 and 7.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 15 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
With respect to claim 15, the claim contains embodiments which lie outside the scope of parent claim 14. For example, Compound I contains the limitation that j is an integer of 1 to 76, however, when j is L1, then a compound wherein L1 and L2 are the same is formed. Parent claim 14 requires that when L3 is absent, then L1 and L2 are absent. Thus, such a limitation is not further limiting, and it is unclear what is being claimed.
In continuing examination, only compounds which result in a product with different definitions for L1 and L2 are being considered.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 15 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
With respect to claim 15, the claim contains embodiments which lie outside the scope of parent claim 14. For example, Compound I contains the limitation that j is an integer of 1 to 76, however, when j is L1, then a compound wherein L1 and L2 are the same is formed. Parent claim 14 requires that when L3 is absent, then L1 and L2 are absent. Thus, such a limitation is not further limiting.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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 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.
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.
Claims 1-6, 8, 11, 17, 21, 22, and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (WO 2019/240462 A1) and further in view of Lee et al. (US 2021/0013430 A1).
With respect to claim 1, Choi discloses compound BD-13 (page 32 of the untranslated document), which is pictured below.
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Compound BD-13 is derived from Choi Chemical Formula 3 (paragraphs 18 and 19), which is pictured below.
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Choi also teaches that adjacent substituents can bond to form a ring (paragraphs 117 and 118) and compounds of the invention may also be represented by Chemical Formula 3-2 (paragraph 153) which is pictured below.
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Choi also teaches that in this formula, Y1 through Y3 are oxygen atoms (paragraphs 165-166), and that A3 is a polycyclic ring (paragraph 22) such as dibenzofuran (paragraph 112), as pictured above.
Choi includes each element claimed, with the only difference between the claimed invention and Choi being a boron center, and the above combination 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 linking atom from the finite list of possible linking groups to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when used in an organic light-emitting device, provides an organic light-emitting device with low driving voltage, high luminous efficiency, and good lifespan characteristics in an emission layer (paragraph 6), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Choi does not teach nor fairly suggest replacing the boron atom with an aluminum, gallium, or indium atom.
In analogous art, Lee teaches an organic electroluminescence device comprising an analogous condensed, polyheterocyclic compound which shows improved emission efficiency (abstract).
Lee teaches that in the condensed, polyheterocyclic compound of the embodiment, the metalloid center should be aluminum, gallium, or indium, instead of a boron atom. Lee teaches that when a ring-forming central atom is aluminum, gallium, or indium, instead of boron, the compound shows multiple resonances which allow for easy separation of HOMO and LUMO states in one molecule, and also for the compound to emit delayed fluorescence. Lee explains that because aluminum, gallium, and indium are relatively large sized atoms, when compared to analogous compounds with a boron atom, the difference between the lowest triple excitation energy level and the lowest singlet excitation energy level is decreased, resulting in improved emission efficiency.
Choi teaches a boron-containing condensed, polyheterocyclic compound with a condensed moiety analogous to instant Formula II, as discussed above. The instant claims are drawn to such a similar compound, which is different from Choi because the claims require an aluminum, gallium, or indium atom in place of the boron atom in the compound of Choi. Lee teaches improvement of a similar condensed, polyheterocyclic compound by replacing a central boron atom with an aluminum, gallium, or indium atom, which results in easy separation of the HOMO and LUMO in the compound, decreased band gap, and improved TADF emission efficiency because of the increased relative size of aluminum, gallium, or indium compared to boron. A person having ordinary skill in the art could have applied the known improvement of replacing the boron atom in the compound Choi with an aluminum, gallium, or indium atom, with a predictable result of easy separation of the HOMO and LUMO in the compound, decreased band gap, and improved TADF emission efficiency because of the increased relative size of aluminum, gallium, or indium compared to boron, as taught by Lee (see MPEP 2143, rationale C).
Such a modification produces a compound which meets the requirements of instant Formula I when M is aluminum, gallium, or indium, X1-X11 are carbon atoms, L1 through L3 are oxygen atoms, RA is not present, RB and RC are monosubstituted alkyl (t-butyl) groups, a structure of Formula II is fused to X1 and X2, wherein in Formula II, Z is coordinated to X2, and Y is coordinated to X1, ring D is a 6-membered carbocyclic (benzene) ring, Y is oxygen, Z is carbon, and RD represents no substitution.
With respect to claim 2, Choi in view of Lee teaches the compound of claim 1, and RA is not present, RB and RC are monosubstituted alkyl (t-butyl) groups, and R1 through R3 are not present.
With respect to claim 3, Choi in view of Lee teaches the compound of claim 1, and the compound comprises exactly one structure of Formula II.
With respect to claim 4, Choi in view of Lee teaches the compound of claim 1, and ring D is a 6-membered carbocyclic ring, as discussed above.
With respect to claim 5, Choi in view of Lee teaches the compound of claim 1, and L1 through L3 are oxygen atoms, as discussed above.
With respect to claim 6, Choi in view of Lee teaches the compound of claim 1, and L1 through L3 are oxygen atoms, as discussed above.
With respect to claims 8 and 11, Choi in view of Lee teaches the compound of claim 1, as discussed above.
Choi also teaches that A3 may be an azadibenzofuran, such as the partial structure pictured below (paragraph 111).
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Such a modification produces a compound which meets the requirements instant claims 8 and 11 when X3 is a nitrogen atom.
Choi includes each element claimed, with the only difference between the claimed invention and Choi being a lack of the aforementioned azadibenzofuran 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 taught definition for A3 from the finite list of possible polycyclic definitions for A3 and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound which, when used in an organic light-emitting device, provides an organic light-emitting device with low driving voltage, high luminous efficiency, and good lifespan characteristics in an emission layer (paragraph 6), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 17, Choi in view of Lee teaches the compound of claim 1, and Choi also teaches an organic light emitting device (OLED) comprising an anode, a cathode, an organic layer disposed between the electrodes (paragraphs 338 through 343), and the light emitting layer comprises the compound of the invention, such as the compound of claim 1 (see paragraph 347, Table 4 and Example device 5), as discussed above.
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 the compound of Choi and Lee in the organic layer of a device with the claimed structure, as taught by Choi.
With respect to claims 21 and 22, Choi in view of Lee teaches the compound of claim 1, and L1 and L2 are oxygen and the compound does not comprise nitrogen, as discussed above.
With respect to claim 24, Choi in view of Lee teaches the compound of claim 1, and L3 is present, as discussed above.
Claims 14-16 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (WO 2019/240462 A1).
With respect to claim 14, Choi discloses compound BD-13 (page 32 of the untranslated document), which is pictured below.
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Compound BD-13 is derived from Choi Chemical Formula 3 (paragraphs 18 and 19), which is pictured below.
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Choi also teaches that adjacent substituents can bond to form a ring (paragraphs 117 and 118) and compounds of the invention may also be represented by Chemical Formula 3-2 (paragraph 153) which is pictured below.
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Choi also teaches that in this formula, Y1 and Y2 are oxygen atoms (paragraph 165), and Y3 is NR13 (paragraph 166), wherein R13 is phenyl (paragraph 184, line 2), and that A3 is a polycyclic ring (paragraph 22) such as dibenzofuran (paragraph 112), as pictured above.
Such a modification produces a compound with the structure below.
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The compound of Choi has the structure above when, L1 and L3 are oxygen atoms, L2 is NR2 wherein R2 is aryl (phenyl), RB and RC are a C4 alkyl (t-butyl) group, and RA’ is absent.
Choi includes each element claimed, with the only difference between the claimed invention and Choi a lack of the above linking group combination 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 linking atom from the finite list of possible linking groups to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when used in an organic light-emitting device, provides an organic light-emitting device with low driving voltage, high luminous efficiency, and good lifespan characteristics in an emission layer (paragraph 6), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 15, Choi teaches the compound of claim 14, as discussed above.
Choi also teaches that c1 and c2 are 0 (paragraph 26), so that A1 and A2 are unsubstituted.
Such a modification produces instant Compound VII(L1)(L1)(L1)(L12)(R1).
Choi includes each element claimed, with the only difference between the claimed invention and Choi being a lack of the aforementioned combination 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 from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound which, when used in an organic light-emitting device, provides an organic light-emitting device with low driving voltage, high luminous efficiency, and good lifespan characteristics in an emission layer (paragraph 6), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 16, Choi teaches the compound of claim 14, as discussed above.
Compound BD-13, pictured and discussed above, is derived from Choi Chemical Formula 3 (paragraphs 18 and 19), which is pictured below.
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Choi also teaches that in Formula 3, c1 and c2 are 0 (paragraph 26), so that A1 and A2 are unsubstituted, Y1 is NR11 (paragraph 165), as pictured above, and R11 is an unsubstituted phenyl group (paragraph 184, line 2), and Y2 is an oxygen atom (paragraph 165).
Examiner notes that Choi is also not limiting with respect to the positioning of the dibenzofuran group at A3.
Such modifications produce the instant second embodiment, which is pictured below.
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Choi includes each element claimed, with the only difference between the claimed invention and Choi a lack of the above linking group combination 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 linking atom from the finite list of possible linking groups to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when used in an organic light-emitting device, provides an organic light-emitting device with low driving voltage, high luminous efficiency, and good lifespan characteristics in an emission layer (paragraph 6), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Claims 18 and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (WO 2019/240462 A1) and further in view of Lee et al. (US 2021/0013430 A1) as applied above, and further in view of Hatakeyama et al. (US 2018/0069182 A1).
With respect to claims 18 and 19, Choi in view of Lee teaches the OLED of claim 17, as discussed above.
However, while Choi teaches that the light-emitting layer may further include dopant materials (paragraph 310), such as iridium complexes (paragraph 311, line 7), neither Choi nor Lee teaches or fairly suggests a phosphorescent transition metal emitter of any of the instant formulae.
In analogous art, Hatakeyama teaches fused, polycyclic boron compounds (abstract) for use in the emitting layer of an organic light emitting diode (paragraph 0042).
Similar to Choi, Hatakeyama teaches the emitting layer may further comprise dopant materials (paragraph 0142), however, Hatakeyama gives specific examples of phosphorescent dopant materials which include Ir(ppy)3 (see Table 3 on page 33), which is pictured below.
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This compound meets the requirements of the instant claim when the ligand comprises the partial formula below (row 2, column 2 of page 28 of the instant claims).
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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 use the compound Ir(ppy)3 as the phosphorescent dopant material in the emitting layer of the device of Choi and Lee, as taught by Hatakeyama.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (WO 2019/240462 A1) and further in view of Lee et al. (US 2021/0013430 A1) as applied above, and further in view of Xia et al. (US 2015/0214494 A1).
With respect to claim 20, Choi discloses compound BD-13 (page 32 of the untranslated document), which is pictured below.
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Compound BD-13 is derived from Choi Chemical Formula 3 (paragraphs 18 and 19), which is pictured below.
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Choi also teaches that adjacent substituents can bond to form a ring (paragraphs 117 and 118) and compounds of the invention may also be represented by Chemical Formula 3-2 (paragraph 153) which is pictured below.
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Choi also teaches that in this formula, Y1 through Y3 are oxygen atoms (paragraphs 165-166), and that A3 is a polycyclic ring (paragraph 22) such as dibenzofuran (paragraph 112), as pictured above.
Choi includes each element claimed, with the only difference between the claimed invention and Choi being a boron center, and the above combination 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 linking atom from the finite list of possible linking groups to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when used in an organic light-emitting device, provides an organic light-emitting device with low driving voltage, high luminous efficiency, and good lifespan characteristics in an emission layer (paragraph 6), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Choi does not teach nor fairly suggest replacing the boron atom with an aluminum, gallium, or indium atom.
In analogous art, Lee teaches an organic electroluminescence device comprising an analogous condensed, polyheterocyclic compound which shows improved emission efficiency (abstract).
Lee teaches that in the condensed, polyheterocyclic compound of the embodiment, the metalloid center should be aluminum, gallium, or indium, instead of a boron atom. Lee teaches that when a ring-forming central atom is aluminum, gallium, or indium, instead of boron, the compound shows multiple resonances which allow for easy separation of HOMO and LUMO states in one molecule, and also for the compound to emit delayed fluorescence. Lee explains that because aluminum, gallium, and indium are relatively large sized atoms, when compared to analogous compounds with a boron atom, the difference between the lowest triple excitation energy level and the lowest singlet excitation energy level is decreased, resulting in improved emission efficiency.
Choi teaches a boron-containing condensed, polyheterocyclic compound with a condensed moiety analogous to instant Formula II, as discussed above. The instant claims are drawn to such a similar compound, which is different from Choi because the claims require an aluminum, gallium, or indium atom in place of the boron atom in the compound of Choi. Lee teaches improvement of a similar condensed, polyheterocyclic compound by replacing a central boron atom with an aluminum, gallium, or indium atom, which results in easy separation of the HOMO and LUMO in the compound, decreased band gap, and improved TADF emission efficiency because of the increased relative size of aluminum, gallium, or indium compared to boron. A person having ordinary skill in the art could have applied the known improvement of replacing the boron atom in the compound Choi with an aluminum, gallium, or indium atom, with a predictable result of easy separation of the HOMO and LUMO in the compound, decreased band gap, and improved TADF emission efficiency because of the increased relative size of aluminum, gallium, or indium compared to boron, as taught by Lee (see MPEP 2143, rationale C).
Such a modification produces a compound which meets the requirements of instant Formula I when M is aluminum, gallium, or indium, X1-X11 are carbon atoms, L1 through L3 are oxygen atoms, RA is not present, RB and RC are monosubstituted alkyl (t-butyl) groups, a structure of Formula II is fused to X1 and X2, wherein in Formula II, Z is coordinated to X2, and Y is coordinated to X1, ring D is a 6-membered carbocyclic (benzene) ring, Y is oxygen, Z is carbon, and RD represents no substitution.
However, while Choi discloses an organic light emitting device (OLED) comprising an anode, a cathode, an organic layer disposed between the electrodes (paragraphs 338 through 343), and the light emitting layer comprises compound BD-13 (see paragraph 347, Table 4 and Example device 5), neither Choi nor Lee teaches or fairly suggests a consumer product.
In analogous art, Xia teaches an organic electroluminescent device (paragraph 0003).
Xia teaches that opto-electronic devices, such as organic light emitting devices, that make use of organic materials are becoming increasingly desirable for a number of reasons including cost advantage, and inherent properties of organic materials such as their flexibility which make them well suited for fabrication on flexible substrates.
Xia goes on to teach that OLEDs are increasingly interesting technology for use in applications such as consumer products such as flat panel displays, illumination, and backlighting (paragraph 0005).
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 use the OLED of Choi and Lee in a consumer product such as a flat panel display, as Xia teaches that organic materials are becoming increasingly desirable for a number of reasons including cost advantage, and inherent properties of organic materials such as their flexibility which make them well suited for fabrication on flexible substrates.
Claims 1-2, 4, 8, 11, 17, 20, and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2020/0098991 A1) and further in view of Lee et al. (US 2021/0013430 A1).
With respect to claim 1, Kim discloses compound 61 (page 19), which is pictured below.
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This compound is derived from Kim Formula 1 (paragraph 0048), which is pictured below.
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Kim also teaches that Y1 and Y2 can be sulfur atoms (paragraphs 0011 and 0012), and A3 can be selected as an azadibenzofuran group (paragraph 0055 and 0056 line 36).
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a boron center, two sulfur linking atoms, and a nitrogen atom in the dibenzofuran moiety 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 linking atom or substituent from the finite lists of possible linking groups and substituents to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when included in an organic light emitting device, emits in the near-IR region while having low driving voltage and high efficiency (paragraph 0384), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Kim does not teach nor fairly suggest replacing the boron atom with an aluminum, gallium, or indium atom.
In analogous art, Lee teaches an organic electroluminescence device comprising an analogous condensed, polyheterocyclic compound which shows improved emission efficiency (abstract).
Lee teaches that in the condensed, polyheterocyclic compound of the embodiment, the metalloid center should be aluminum, gallium, or indium, instead of a boron atom. Lee teaches that when a ring-forming central atom is aluminum, gallium, or indium, instead of boron, the compound shows multiple resonances which allow for easy separation of HOMO and LUMO states in one molecule, and also for the compound to emit delayed fluorescence. Lee explains that because aluminum, gallium, and indium are relatively large sized atoms, when compared to analogous compounds with a boron atom, the difference between the lowest triple excitation energy level and the lowest singlet excitation energy level is decreased, resulting in improved emission efficiency.
Kim teaches a boron-containing condensed, polyheterocyclic compound with a condensed moiety analogous to instant Formula II, as discussed above. The instant claims are drawn to such a similar compound, which is different from Choi because the claims require an aluminum, gallium, or indium atom in place of the boron atom in the compound of Kim. Lee teaches improvement of a similar condensed, polyheterocyclic compound by replacing a central boron atom with an aluminum, gallium, or indium atom, which results in easy separation of the HOMO and LUMO in the compound, decreased band gap, and improved TADF emission efficiency because of the increased relative size of aluminum, gallium, or indium compared to boron. A person having ordinary skill in the art could have applied the known improvement of replacing the boron atom in the compound Kim with an aluminum, gallium, or indium atom, with a predictable result of easy separation of the HOMO and LUMO in the compound, decreased band gap, and improved TADF emission efficiency because of the increased relative size of aluminum, gallium, or indium compared to boron, as taught by Lee (see MPEP 2143, rationale C).
Such a compound meets the requirements of the instant claim when M is aluminum, gallium, or indium, X1 is a nitrogen atom, X2-X11 are carbon atoms, L1 and L2 are sulfur atoms, L3 is not present, X2 and X3 are fused to a structure of Formula II, wherein X2 is bonded to Z and X3 is bonded to Y, Y is an oxygen atom, Z is a carbon atom, and ring D is a 6-membered carbocyclic (benzene) ring, X5 and X6 are fused to a structure of Formula II, wherein X5 is bonded to Z and X6 is bonded to Y, Y is an oxygen atom, Z is a carbon atom, and ring D is a 6-membered carbocyclic (benzene) ring, and X9 and X10 are fused to a structure of Formula II, wherein X9 is bonded to Y and X10 is bonded to Z, Y is an oxygen atom, Z is a carbon atom, and ring D is a 6-membered carbocyclic (benzene) ring.
With respect to claim 2, Kim in view of Lee teaches the compound of claim 1, and R1 through R3 and RA-RC are not present, as discussed above.
With respect to claim 4, Kim in view of Lee teaches the compound of claim 1, and ring D is a 6-membered carbocyclic ring, as discussed above.
With respect to claim 8, Kim in view of Lee teaches the compound of claim 1, and X1 is nitrogen, as discussed above.
With respect to claim 11, Kim in view of Lee teaches the compound of claim 1, and only X1 is a nitrogen atom.
With respect to claim 17, Kim in view of Lee teaches the compound of claim 1, and Kim also teaches an organic light emitting device (paragraph 0262), which may be included in a consumer product (a personal computer, paragraph 0266), and the organic light emitting device includes an anode, a cathode, an organic layer between the electrodes (paragraph 0046), and the organic layer comprises the compound (paragraph 0007).
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 the compound in the organic layer of an organic light emitting device or consumer product with the claimed device structure, as taught by Kim.
With respect to claim 20, Kim discloses an organic light emitting device (paragraph 0262), which may be included in a consumer product (a personal computer, paragraph 0266), and the organic light emitting device includes an anode, a cathode, an organic layer between the electrodes (paragraph 0046), and the organic layer comprises compound 61 (page 19), which is pictured below.
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269
384
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This compound is derived from Kim Formula 1 (paragraph 0048), which is pictured below.
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239
399
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Kim also teaches that Y1 and Y2 can be sulfur atoms (paragraphs 0011 and 0012), and A3 can be selected as an azadibenzofuran group (paragraph 0055 and 0056 line 36).
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a boron center, two sulfur linking atoms, and a nitrogen atom in the dibenzofuran moiety 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 linking atom or substituent from the finite lists of possible linking groups and substituents to arrive at the compound described above since the combination of elements would have yielded the predictable result of a compound which, when included in an organic light emitting device, emits in the near-IR region while having low driving voltage and high efficiency (paragraph 0384), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Kim does not teach nor fairly suggest replacing the boron atom with an aluminum, gallium, or indium atom.
In analogous art, Lee teaches an organic electroluminescence device comprising an analogous condensed, polyheterocyclic compound which shows improved emission efficiency (abstract).
Lee teaches that in the condensed, polyheterocyclic compound of the embodiment, the metalloid center should be aluminum, gallium, or indium, instead of a boron atom. Lee teaches that when a ring-forming central atom is aluminum, gallium, or indium, instead of boron, the compound shows multiple resonances which allow for easy separation of HOMO and LUMO states in one molecule, and also for the compound to emit delayed fluorescence. Lee explains that because aluminum, gallium, and indium are relatively large sized atoms, when compared to analogous compounds with a boron atom, the difference between the lowest triple excitation energy level and the lowest singlet excitation energy level is decreased, resulting in improved emission efficiency.
Kim teaches a boron-containing condensed, polyheterocyclic compound with a condensed moiety analogous to instant Formula II, as discussed above. The instant claims are drawn to such a similar compound, which is different from Choi because the claims require an aluminum, gallium, or indium atom in place of the boron atom in the compound of Kim. Lee teaches improvement of a similar condensed, polyheterocyclic compound by replacing a central boron atom with an aluminum, gallium, or indium atom, which results in easy separation of the HOMO and LUMO in the compound, decreased band gap, and improved TADF emission efficiency because of the increased relative size of aluminum, gallium, or indium compared to boron. A person having ordinary skill in the art could have applied the known improvement of replacing the boron atom in the compound Kim with an aluminum, gallium, or indium atom, with a predictable result of easy separation of the HOMO and LUMO in the compound, decreased band gap, and improved TADF emission efficiency because of the increased relative size of aluminum, gallium, or indium compared to boron, as taught by Lee (see MPEP 2143, rationale C).
Such a compound meets the requirements of the instant claim when M is aluminum, gallium, or indium, X1 is a nitrogen atom, X2-X11 are carbon atoms, L1 and L2 are sulfur atoms, L3 is not present, X2 and X3 are fused to a structure of Formula II, wherein X2 is bonded to Z and X3 is bonded to Y, Y is an oxygen atom, Z is a carbon atom, and ring D is a 6-membered carbocyclic (benzene) ring, X5 and X6 are fused to a structure of Formula II, wherein X5 is bonded to Z and X6 is bonded to Y, Y is an oxygen atom, Z is a carbon atom, and ring D is a 6-membered carbocyclic (benzene) ring, and X9 and X10 are fused to a structure of Formula II, wherein X9 is bonded to Y and X10 is bonded to Z, Y is an oxygen atom, Z is a carbon atom, and ring D is a 6-membered carbocyclic (benzene) ring.
With respect to claim 22, Kim in view of Lee teaches the compound of claim 1, and neither of L1 and L2 comprises a nitrogen atom.
Conclusion
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/RACHEL SIMBANA/Examiner, Art Unit 1786
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