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 .
Election/Restrictions
Applicant’s election without traverse of Species A wherein X1 is selected from B, P, P(=O), P(=S), Al, Ga, As, Si(R4), or Ge(R4) and Y1 and Y2 are each independently selected from a) O, S, Se, and N(R5) in the reply filed on 06/14/2024 is acknowledged.
Status of Claims
Claims 1, 5, 7-8, and 16 are amended and claims 2-4, 9, 14-15, and 20 are cancelled due to Applicant's amendment dated 09/17/2025. Claims 1, 5-8, 10-13, and 16-19 are pending.
Response to Amendment
The rejections of claims 2-4, 9, 14-15, and 20 as set forth in the previous Office Action are moot because claim 2-4, 9, 14-15, and 20 are cancelled due to the Applicant's amendment dated 09/17/2025.
The objection to claim 7 as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 09/17/2025. The objection is withdrawn.
The rejection of claims 1, 5-8, 10-13, and 17-18 under 35 U.S.C. 102(a)(2) as being anticipated by Hatakeyama (US 2022/0006012 A1) is overcome due to the Applicant's amendment dated 09/17/2025. The objection is withdrawn.
The rejection of claim 16 under 35 U.S.C. 103 as being unpatentable over Hatakeyama in view of Kawai (US 2004/0150327 A1) and Duan ‘666 (US 2020/0006666 A1) is overcome due to the Applicant's amendment dated 09/17/2025. The objection is withdrawn.
The rejection of claim 19 under 35 U.S.C. 103 as being unpatentable over Hatakeyama in view of Liu (US 2021/0391552 A1) is overcome due to the Applicant's amendment dated 09/17/2025. The objection is withdrawn.
Response to Arguments
Applicant’s arguments on pages 32-36 of the reply dated 09/17/2025 with respect to the rejection of claims 1, 5-8, 10-13, and 16-19 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –On pages 32-36, Applicant argues the cited references fail to teach the claims as amended which require at least one of R3a to R3c, one of R1a to R1d, one of R2a to R2d, one of R5b to R5d, and one of R5g to R5j to be represented by Formula 1-1.
Examiner's response –As discussed in greater detail in the rejection below, Kawai and Duan ‘666 teach that t-butyl groups and groups represented by the claimed Formula 1-1 are expected to provide the same benefit. Thus, Kawai and Duan ‘666 provide motivation to substitute the t-butyl groups of compound 1-132 with substituents represented by the claimed Formula 1-1. Accordingly, the cited references teach the claims as amended.
Information Disclosure Statement
Multiple Foreign Reference and Non-Patent Literature documents were submitted on 09/29/2025. However, these documents were not accompanied by an information disclosure statement.
An information disclosure statement requires the following: (1) a list of all patents, publications, applications, or other information submitted for consideration by the Office; (2) U.S. patents and U.S. patent application publications listed in a section separately from citations of other documents; (3) the application number of the application in which the information disclosure statement is being submitted on each page of the list; (4) a column that provides a blank space next to each document to be considered, for the examiner’s initials; and (5) a heading that clearly indicates that the list is an information disclosure statement.
The Foreign Reference and Non-Patent Literature documents dated 09/29/2025 have been placed in the application file, but the information referred to therein has not been considered.
Claim Objections
Claim 16 is objected to because of the following informalities:
It is recommended in claim 16 to replace “Formula 1” with “Formula 2A” for consistency. Appropriate correction is required.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 5-8, 10-13 and 16-18 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama (US 2022/0006012 A1) in view of Kawai (US 2004/0150327 A1) and Duan ‘666 (US 2020/0006666 A1).
Regarding claims 1, 5-8, 10-13 and 17-18, Hatakeyama teaches a polycyclic aromatic compound represented by general formula (1) and having a bulky substituent provides an organic EL device with excellent quantum efficiency (abstract). Hatakeyama teaches examples of such devices including Example 4, which comprises an anode, two hole injection layers, two hole transport layers, a luminescent layer comprising a host of BH-1 and 2 wt% of compound 1-132 as a dopant, two electron transport layers, and a cathode (Table 1A on pg. 143; ¶ [0523]-[0528]; structure on pg. 4) (claims 17-18).
(1):
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218
281
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1-132:
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332
337
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Compound 1-132 fails to read on the claimed Formula 2A as each of the t-butyl groups do not read on the claimed Formula 1-1. However, Hatakeyama does teach X1 may be N-R, and R1, R3 to R4, R8 to R11, R12 to R15, and R may each be hydrogen, alkyl, or aryl, among others, wherein at least one hydrogen therein may be replaced by aryl (¶ [0016]-[0017]).
Kawai teaches concentration quenching may be prevented by incorporating a bulky substituent on a molecule structure, as the bulky substituent provides steric hindrance (¶ [0092]). Accordingly, Kawai teaches bulky substituents are those that provide steric hindrance, and such groups prevent concentration quenching.
Duan ‘666 teaches large steric hindrance substituent groups for compounds of organic electroluminescent devices include structures X-2 and X-9, among others (abstract and ¶ [0016]).
X-2:
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63
69
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X-9:
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75
122
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As structures X-2 and X-9 are each a group that provides steric hindrance, they are considered bulky substituents and thus prevent concentration quenching according to Kawai. Accordingly, in light of the teachings of Kawai and Duan ‘666, structure X-9 is a suitable substitute for structure X-2 (t-butyl) as they both are bulky substituents that suppresses concentration quenching.
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 each of the t-butyl groups of compound 1-132 with structure X-9 of Duan ‘666, because Duan ‘666 and Kawai teach structure X-9 is a suitable substituent for t-butyl (structure X-2) as a bulky substituent that suppresses concentration. The substitution would have been one known 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 the dopant in the luminescent layer of the device of Hatakeyama and possess the benefits taught by Hatakeyama, Kawai, and Duan ‘666. See MPEP 2143.I.(B).
In particular, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select structure X-9, because it would have been choosing from a list of suitable groups that provide steric hindrance taught by Duan ‘666, and because Hatakeyama teaches R1, R3 to R4, R8 to R11, R12 to R15, and R may each be hydrogen, alkyl, or aryl, among others, wherein at least one hydrogen therein may be replaced by aryl, and this would have been a choice from a finite number of identified, predictable solutions of a substituent within the scope of Hatakeyama’s general formula (1). One of ordinary skill in the art would have been motivated to produce additional compounds represented by Hatakeyama’s general formula (1) having the benefits taught by Hatakeyama, Kawai, and Duan ‘666 in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified compound 1-132 is reproduced below in comparison to the claimed Formulas 2A, 1-1, and 1-2.
2A:
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221
338
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1-1:
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32
216
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1-2:
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115
212
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modified 1-132:
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528
498
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The modified Compound 1-132 reads on the claimed formulas wherein:
X1 is B (claim 5);
R1a, R1b, R1d, R2a, R2b, R2d, R3a, R3c, R5a, R5b, R5d, R5e, R5f, R5g, R5i, and R5j are each hydrogen, R1c, R2c, R3b, R5c, and R5h are each is a group represented by Formula 1-1 (claim 8);
in Formula 1-1:
L11 is a single bond (claims 6-7); a11 is 1; A11 is a group represented by Formula 1-2; m11 is an integer of 1 (claim 11);
L1 is not required to be present; n is 0;
in the case of R1c, R2c, R5c, and R5h, R11 to R12 are each an unsubstituted C1 alkyl group and R13 is an unsubstituted C6 aryl group of phenyl (claim 10); and
in the case of R3b, R11 to R13 are each an unsubstituted C6 aryl group of phenyl (claim 10).
In the case of R1c, R2c, R5c, and R5h, Formula 1-2 is represented by Formula 1-2a wherein R22 is hydrogen and d22 is an integer of 5. In the case of in the case of R3b, Formula 1-2 is represented by Formula 1-2c wherein R21 to R23 are each hydrogen and d21 to d23 are each 5 (claims 12-13).
Regarding claim 16, Hatakeyama in view of Kawai and Duan ‘666 teach the modified compound 1-132 as described above with respect to claim 1.
modified 1-132:
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528
498
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The modified compound 1-132 fails to read on a claimed compound. However, in Hatakeyama’s general formula (1), Z1 is a bulky substituent that suppresses concentration quenching, such as an alkyl group having 1 to 4 carbons wherein at least one hydrogen may be replaced with aryl having 6 to 12 carbons (abstract; ¶ [0014], [0018], [0036], and [0051]).
Kawai teaches concentration quenching may be prevented by incorporating a bulky substituent on a molecule structure, as the bulky substituent provides steric hindrance (¶ [0092]). Accordingly, Kawai teaches bulky substituents are those that provide steric hindrance, and such groups prevent concentration quenching.
Duan ‘666 teaches large steric hindrance substituent groups for compounds of organic electroluminescent devices include structure X-9, among others (abstract and ¶ [0016]).
X-9:
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75
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As structure X-9 is a group that provides steric hindrance, it is considered a bulky substituent and thus it prevents concentration quenching according to Kawai. Accordingly, structure X-9 is a suitable bulky substituent that suppresses concentration quenching.
Therefore, given that Hatakeyama teaches Z1 is a bulky substituent that suppresses concentration quenching and may be an alkyl group having 1 to 4 carbons wherein at least one hydrogen may be replaced with aryl having 6 to 12 carbons, 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 triphenylmethyl group of Z1 with structure X-9 of Duan ‘666, because Duan ‘666 and Kawai teach structure X-9 is a suitable bulky substituent that suppresses concentration. The substitution would have been one known 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 the dopant in the luminescent layer of the device of Hatakeyama and possess the benefits taught by Hatakeyama. See MPEP 2143.I.(B).
In particular, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select structure X-9 as the bulky substituent, because it would have been choosing from a list of suitable groups that provide steric hindrance taught by Duan ‘666, and because Hatakeyama teaches Z1 may be a bulky substituent of an alkyl group having 1 to 4 carbons wherein at least one hydrogen may be replaced with aryl having 6 to 12 carbons, and this would have been a choice from a finite number of identified, predictable solutions of bulky substituent. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Hatakeyama’s general formula (1) having the benefits taught by Hatakeyama in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The resulting compound reads on the claimed compound 1.
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama (US 2022/0006012 A1) in view of Kawai (US 2004/0150327 A1) and Duan ‘666 (US 2020/0006666 A1) as applied to claim 18 above, and further in view of Liu (US 2021/0391552 A1).
Regarding claim 19, Hatakeyama in view of Kawai and Duan ‘666 teach the device of Example 4 a luminescent layer comprising a host of BH-1 and 2 wt% of the modified compound 1-132 as a dopant, as described above with respect to claim 18.
Hatakeyama fails to teach the luminescent layer further comprises a sensitizer and fails to teach an amount of the host in the luminescent layer is greater than a total combined amount of the dopant and the sensitizer in the luminescent layer.
Liu teaches an organic luminescent device including a host material, a TADF sensitizer, and a fluorescent-luminescent material, wherein:
|LUMOhost – LUMOsensitizer| ≤ 0.4 eV;
|HOMOhost – HOMOsensitizer| ≤ 0.4 eV;
|LUMOfluorescent-luminescent | ≤ | LUMOhost| and |LUMOfluorescent-luminescent | ≤ | LUMOsensitizer|; and/or
|HOMOfluorescent-luminescent | ≥ | HOMOhost| and |HOMOfluorescent-luminescent | ≥ | HOMOsensitizer|;
T1_host > T1_sensitizer > T1_fluorescent-luminescent; and
emission-spectrum of the host material overlaps and absorption-spectrum of the TADF sensitizer, and emission-spectrum of the TADF sensitizer overlaps absorption-spectrum of the fluorescent-luminescent material (abstract and ¶ [0026]). A mole ratio of the host material is 50-90%, the mole ratio of the TADF sensitizer is 5-50%, and a mole ratio of the fluorescent luminescent material is 0.2-4% (¶ [0010]). Additionally, S1_host - T1_host ≥ 0.25 eV as this facilitates the RISC of the triplet excitons of the host material to transition through the RISC (reverse intersystem crossing) (¶ [0064]). Similarly, S1_sensitizer - T1_sensitizer ≥ 0.25 eV as this facilitates the RISC of the triplet excitons of the TADF sensitizer (¶ [0065]). Such a device may obtain reduced driving voltage and increased luminous efficiency (¶ [0099]).
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 further provide in the luminescent layer a mole ratio of 5-50% of a TADF sensitizer such that S1_sensitizer - T1_sensitizer ≥ 0.25 eV is satisfied; to substitute the host compound BH-1 with a host compound such that the maximum value of the energy level difference of S1_host and T1_host is 0.25 eV; and to select the TADF sensitizer and host compound such that conditions (i)-(v) above are satisfied, based on the teaching of Liu. The motivation for doing so would have been to facilitate the RISC of the triplet excitons of the host material to transition through the RISC; facilitate the RISC of the triplet excitons of the TADF sensitizer; and to provide a device with reduced driving voltage and increased luminous efficiency, as taught by Liu.
The resulting luminescent layer comprises 2 wt% of the modified compound 1-132 and 5-50 wt% of a sensitizer. A prima facie case of obviousness exists where the claimed ranges overlap or lie inside ranges disclosed by the prior art. See MPEP 2144.05.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BRAELYN R WATSON whose telephone number is (571)272-1822. The examiner can normally be reached M-F 7:30am-5pm.
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/B.R.W./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786