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 .
DETAILED ACTION
Claim Interpretation
Claim 5 recites that every R11 through R28 groups in formula (I) and (II) of claim 4 are selected from the following structures
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. However, as claimed, this means that none of R11 through R28 may be equal to hydrogen. For example, as claimed, compounds of formula (I) in light of claim 5 would have 10 groups selected from those groups above bonded at every available carbon atom of the anthracene group or 8 groups selected from those groups above bonded at every available carbon atom of the naphthalene group. It is doubtful that this is what Applicants had intended when drafting this claim as none of Applicants compounds disclosed in their originally filed specification even comes close to satisfying claim 5 as drafted. For purposes of further examination, claim 5 will be given the additional interpretation that each of R11 through R28 is equal to a hydrogen atom or a group selected from the structures recited above.
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.
Claims 5 and 10 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 5 recites the limitation that R701 to R704 in multiple occurrences may be site linted to other groups. This phrase is structurally vague and open-ended and creates an indefiniteness issue because it does not define what those “other groups” are, and the claims does not specify the nature of the linkage.
Additionally, the limitation “any combination thereof” is a catch-all phrase which is applied at the end of a long, complex list of diverse chemical functional groups (ranging from simple halogens to cross-linkable groups and multi-ring heteroaromatics). This phrase renders the claim indefinite as it leaves one guessing whether it means sequential substitution, fused rings, or branched combinations. Additionally, all of the 12 groups recited in claim 5 do not show how said groups are attached to one of formula (I) or formula (II) of claim 4, rendering the claim indefinite. Claim 10 is included in these rejections as it is dependent on claim 5.
Claim 16 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 16 recites that R11 to R28 can be independently selected from the Markush as recited. However, the term “can be” raises the question as to whether or not these groups can also be selected from other groups which are not part of the Markush group, which renders the claim indefinite. It is suggested that Applicants amend “can be” to “are” in order to overcome this rejection.
Claim 16 is further rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. The limitation “any combination thereof” is a catch-all phrase which is applied at the end of a long, complex list of diverse chemical functional groups (ranging from simple halogens to cross-linkable groups and multi-ring heteroaromatics). This phrase renders the claim indefinite as it leaves one guessing whether it means sequential substitution, fused rings, or branched combinations.
Claim Rejections - 35 USC § 102
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-5, 11, and 13-15 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Tasaki et al. (US 2023/0042023) when taken with the evidentiary reference of Kawamura (US 2024/0284693).
Claims 1 and 2: Tasaki et al. teaches the co-deposition of BH-2 and D-BH-2 in device example 2. Compound BH-2 has the structure
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and compound D-BH-2 has the structure
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(page 651). Prior to deposition, the compounds BH-2 and D-BH-2 are present as an organic mixture where BH-2 can be referred to as a first organic compound H1 and D-BH-2 can be referred to as a second organic compound H2.
While Tasaki et al. does not teach the HOMO, LUMO, singlet, and triplet values of compound BH-2, Kawamura et al. teaches compound BH2-a, whose structure is taught on page 410. It can readily be seen that compound BH2-a of Kawamura et al. is identical to compound BH-2 of Tasaki et al. Kawamura et al. further teaches that compound BH2-a has a HOMO energy level of -5.98 eV, a LUMO energy level of -2.97 eV, a singlet energy level, S1, of 3.01 eV, and a triplet energy level, T1 of 1.90 eV (Table 1, page 412). The singlet-triplet energy gap DEST of compound BH-2 is calculated to be 1.11 eV which is greater than 0.6 eV as required by claim 1.
While the HOMO, LUMO, singlet, and triplet energy values of compound D-BH-2 are not disclosed by Tasaki et al. or Kawamura et al., a person having ordinary skill in the art would have expected that the HOMO, LUMO, singlet, and triplet energy values of D-BH-2 to be substantially the same as compound BH-2. It is known that the HOMO, LUMO, singlet, and triplet energy levels of an organic compound are determined entirely by its p-conjugated system. Because hydrogen and deuterium are isotopes of the same element, they carry the same nuclear charge and share the exact same number of valence electrons. Replacing hydrogen with deuterium does not alter the configuration, spatial distribution, or density of the p-electron cloud across the anthracene and naphthyl rings of BH-2 and D-BH-2. And while deuterium is marginally more electron-donating than hydrogen due to the shorter C-D bond, this effect is very minor. By this logic, the Ex values of BH-2 and D-BH-2 would be expected to be equal to, or very closely equal to the HOMO-LUMO gap of BH-2 itself since the HOMO and LUMO energy levels of BH-2 and D-BH-2 would be nearly identical.1 The Ex value would therefore be expected to be at or very close to 3.01 eV. As such, the expression Ex–T1 is calculated to be 3.01 eV – 1.90 eV, or 1.11 eV which is greater than 0.6 eV as required by claim 1. Additionally, because the LUMO energy levels of BH-2 and D-BH-2 would be expected to be identical or very nearly identical so the expression HOMO(H2) ≥ HOMO(H1) + 0.10 eV would be expected to be satisfied. Additionally, the expression, │EX – ES1│is estimated to be close to or equal to zero (3.01 eV – 3.01 eV), which is less than 0.4 eV which satisfies claim 2.
Claim 3: The compounds BH-2 and D-BH-2 are organic compounds which consist of aromatic groups containing 12 and 18 carbon atoms, which satisfies claim 3.
Claim 4: The compound BH-2 and D-BH-2 are organic compounds which includes groups satisfying formula (I) and (II) of claim 1 with all R groups equal to hydrogen or deuterium with the exception of R13, R18, R21, and R22 which represent attachment points between Formulae (I) and (II).
Claim 5: Compounds BH-2 and D-BH-2 have R13 and R18 equal to the 8th group recited in claim 5 with all Y groups equal to CH except for one Y group which is bonded at the R13 and R18 positions of the anthracene. Additionally, the R11, R12, R14-R17, R19, and R20 groups are equal to hydrogen or deuterium.
Claim 11: In the pre-mix taught in paragraph 0851 of Tasaki et al. is a thermally activated delayed fluorescent dopant (BD-1) which anticipates the limitations of claim 11.
Claims 13-15: The organic light-emitting device (device example 2) as taught in Table 2 of Tasaki et al. anticipates the device limitations of claims 13-15.
Claims 1-5 and 11-15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kim et al. (JP-2015018883) when taken with the evidentiary references Toyoshima et al. (WO 2023/038086) and Nishimura et al. (US 2017/0110667). Copies of the original and a machine translation of Kim et al. are included with this Office action.
Claims 1 and 2: Kim et al. teaches light-emitting devices which comprise and anode, a hole transport region, an emission region, an electron transport region, and a cathode. The emission region comprises a mixture of two anthracene-based host materials and a dopant material. One device example employs the anthracene-based host materials BH-a and BH-b, whose structures are
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(page 105). Kim et al. teaches that BH-a, BH-b, and a dopant are co-evaporated to form said emission region. Therefore, Kim et al. explicitly teaches an organic mixture comprising a first organic compound and a second organic compound.
Kim et al. further teaches that the singlet energy level (S1) of BH-a is 3.0 eV and the S1 of compound BH-b is also 3.0 eV. Kim et al. further teaches that the ionization potential of BH-a and BH-b are 6.0 eV and 5.9 eV, respectively. It is known and customary in the OLED area that, while not strictly identical, the ionization potential of a compound and the HOMO energy level of a compound are used interchangeably.2 Kim et al. further teaches that the electron affinity of BH-a and BH-b are 3.0 eV and 2.9 eV, respectively. It is known and customary in the OLED area that, while not strictly identical, the electron affinity of a compound and the LUMO energy level of a compound are used interchangeably.1 For this reason, it can reasonably be said that the HOMO energy level of compound BH-a is 6.0 eV and the HOMO energy level of compound BH-b is 5.9 eV. If BH-a is assigned to be the second host material and BH-b is assigned to be the second host material, then the expression HOMO(H2) ≥ HOMO(H1) + 0.10 eV would be satisfied (6.0 eV = 5.9 eV + 0.10 eV).
Kim et al. does not teach the triplet energy level of compound BH-a. However, the triplet energy level of compound BH-a is known art as taught in the evidentiary reference Toyoshima et al. Compound BH-H of Toyoshima et al., whose structure is taught on page 370, is identical to compound BH-a of Kim et al. The table taught on page 384 of Toyoshima et al. teaches that compound BH-H has a triplet energy level of 1.87 eV.
Kim et al. does not teach the triplet energy level of compound BH-b. However, the triplet energy level of compound BH-b is known in the prior art as taught in the evidentiary reference Nishimura et al. Table 1 of Nishimura et al. teaches that the triplet energy level of compound BH-b (which is referred to as compound BH-3 by Nishimura et al.) is 1.8 eV. Page 23 of Nishimura et al. shows the compound BH-3 to be identical to compound BH-b of Kim et al. Given the teachings of Kim et al. and the evidentiary references of Toyoshima et al. and Nishimura et al., the HOMO, LUMO, singlet, and triplet energy levels of compounds BH-a and BH-b are known. The singlet-triplet energy gap of these two compounds are very high, and calculated to be 1.13 eV for BH-a (3.0 eV – 1.87 eV) and calculated to be 1.2 eV for BH-b (3.0 eV – 1.8 eV). As such, the DEST(H1) and DEST(H2) are greater than 0.6 eV as required by claim 1.
The difference between the HOMO of BH-a and the LUMO of BH-b is 3.1 eV and the difference between the HOMO of BH-b and the LUMO of BH-a is 2.9 eV. As such, the value EX is equal to 2.9 eV. Since the triplet energy levels of BH-a and BH-b are both below 2.0 eV, the expression EX – T1(H1) and EX – T1(H2) is greater than 0.6 eV. Last, the expressions │EX – ES1(H1)│and │EX – ES1(H2)│are less than 0.4 eV since EX is very close in energy to the singlet energy values of BH-a and BH-b, specifically, 2.9 – 3.0, or 0.1 eV in both cases.
Claims 3 and 4: The host materials BH-a and BH-b as taught by Kim et al. satisfy claims 3 and 4 as they both comprise a group of formula (I) with R13 and R18 being equal to aryl or heteroaryl groups which satisfy claim 4 and all remaining R groups being equal to hydrogen atoms.
Claim 5: Using the claim interpretation above, compounds BH-a and BH-b satisfy claim 5 in that the groups bonded at the R13 and R18 positions satisfy one or more of the 6th, 7th, and 8th structures of claim 5.
Claims 11 and 13-15: Device example 1 of Kim et al. comprises an emission layer which consists of BH-a, BH-b, and a thermally activated delayed fluorescence material which satisfies claim 11. The device example is an organic light-emitting device which satisfies the limitations of claims 13 and 14.
Claim 12: In a preferable embodiment, Kim et al. explicitly teaches that a solution of the first host and second host which are dissolved in a solvent, is favorable so as to allow for solution deposition (bottom of page 29 of the machine translation). As such, it is at once envisaged to prepare a solution of any of the exemplified mixed host materials, including BH-a and BH-b.
Claim 16 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Cranor et al. (US 2010/0327240).
Cranor et al. teaches many compounds which anticipate the structural limitations of formula (I) of claim 16. One such compound is the compound shown in Figure 90 which has the structure
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. As applied to Formula 1, variables R11, R12, R14-R17, R19, and R20 are equal to hydrogen atoms, R13 is equal to the electron-donating p-methoxyphenyl group, and R18 is equal to the electron accepting group pentafluorophenyl.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102 of this title, 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.
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 1-11 and 13-15 are rejected under 35 U.S.C. 103 as being unpatentable over Ricks et al. (US 2006/0159952) when taken with the evidentiary references Ieuji et al. (Nature Communications, 2019, 10:5283), Chen et al. (Adv. Mater. 2018, 30, 1804850), Darzi et al. (Mater. Adv. 2023, 4, 3351-3355), and a data sheet from Ossila.
Ricks et al. teaches mixed anthracene derivatives and their employment as host materials in organic electroluminescent devices. Preferred first host materials are selected from compounds A-1 through A-17. Preferred second host materials are selected from B-1 through B-16. Given these teachings it would have been prima facie obvious to a person having ordinary skill in the art to have selected any one of the preferred first host materials and any one of the second host materials so as to prepare a mixture of anthracene-based compounds. The total number of combinations of the 17 compounds A-1 through A-17 and the 16 compounds B-1 through B-16 is sufficiently small that a person of ordinary skill in the art would have easily envisaged all possible combinations as obvious alternatives to the exemplified embodiments taught by Ricks et al. This includes, for example, the selection of compound A-11 as the first host material and compound B-13 as the second host material. Employing compounds A-11 and B-13 in the manner taught by Ricks et al. affords an organic mixture comprising these compounds as taught in the working examples. Compound A-11 has the structure
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and has a HOMO energy level of -5.8 eV and a LUMO energy level of -2.6 eV as evidenced by a technical data sheet from Ossila. Compound A-11 has a singlet energy level of 3.0 eV and a triplet energy level of 1.7 eV as evidenced by Chen et al. (Figure 1). Compound B-13 has the structure
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and includes two electron-accepting fluorine atoms. While the exact HOMO, LUMO, singlet, and triplet energy values of this compound is not taught by Ricks et al. the HOMO, LUMO, singlet, and triplet energy values of the structurally-related compound diphenyl anthracene, which has the structure,
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is known. Specifically, the HOMO energy level of this compound is -5.5 eV and the LUMO energy level is -2.6 eV as evidenced by Darzi et al. (Fig. 5). Further, the singlet energy level of this compound is 2.85 eV and the triplet energy is 1.75 eV as evidenced by Ieuji et al. (Fig. 5). While compound B-13 is not identical to diphenyl anthracene, it is submitted that the electronic properties of compound B-13 and diphenyl anthracene would be sufficiently close to each other given the level of ordinary skill in the art. Because fluorine does not take part in any electronic conjugation, the singlet and triplet energy levels would be expected to be very similar to analogous compounds which do not have fluorine substitution. The electron withdrawing effect of the fluorine atom would be expected to lower both the HOMO and the LUMO properties but such an effect would be expected to be minor such that the expressions of claims 1 and 2 would be satisfied.3
Both compounds A-11 and B-13 comfortably satisfy the DEST requirements of claim 1, having a DEST well above 1.0 eV. Additionally, the LUMO energy levels between these compounds are identical, and the compound B-13 would be expected to have a slightly lower LUMO energy level due to the electron-withdrawing nature of the two fluorine atoms. As such compound B-13 can be assigned as the first host material and the third expression of claim 1 is satisfied [HOMO(H2) ≥ HOMO(H1) + 0.10 eV, which is calculated to be 5.8 eV ≥ 5.5 + 0.10 eV]. Alternatively, if the values are calculated using the negative energy levels, then B-13 can be assigned to be the second host material and the third expression would be satisfied (–5.5 eV≥ –5.8 eV + 0.10 eV). Additionally, because of the very low triplet energy values of compounds A-11 and B-13 (below 2.0 eV) and the large HOMO-LUMO band gaps (around 3.0 eV), the expressions EX – T1(H1) and EX – T1(H2) would be significantly larger than 0.6 eV which satisfies claim 1. Additionally, the high singlet energy values of compounds A-11 and B-13 are very close to the EX values of compounds A-11 and B-13 and as such, the two expressions recited in claim 2 would also be expected to be satisfied.
Claims 3-5: Compounds A-11 and B-13 satisfy the limitations of claim 3 as they both comprise a C14 anthracene ring and said ring satisfies formula (I) of claim 4 with all R groups being equal to hydrogen atoms, methyl, and fluorine-substituted aryl groups, and unsubstituted aryl groups. The groups in compounds A-11 and B-13 satisfy the 7th and 8th groups recited in claim 5.
Claims 6-10: Compound B-11 of Ricks et al. comprises an electron-accepting group (-F) thereby satisfying claims 6-10.
Claim 11: The device examples of Ricks et al. includes a mixture of anthracene-based compounds and a dopant material (singlet emitting material) which satisfies an organic mixture as recited in claim 11.
Claims 13-15: The devices taught and exemplified by Ricks et al. are organic light-emitting devices with the anthracene-based compounds being present in the light-emitting layer, which satisfies the limitations of claims 13-15.
Relevant Art Cited
Additional prior art documents which are relevant to Applicants invention can be found on the attached PTO-892 form.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT S LOEWE whose telephone number is (571)270-3298. The examiner can normally be reached on Monday-Friday from 8 AM to 5 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski, can be reached at telephone number 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Robert S Loewe/Primary Examiner, Art Unit 1766
1 This can be seen, for example in the compounds BH-H and D-BH-H of Toyoshima et al. (WO 2023/038086) which have identical singlet and triplet energy values.
2 See, as one of many examples which teach this, paragraph 0364 of Yang et al. (US 2019/0292181).
3 See for example, Fig. 8 of Li et al. (RSC Adv. 2015, 5, 59027).
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