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
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 7/21/26 has been entered.
Response to Arguments
Applicant’s arguments and amendments filed on 7/21/26 have been fully considered but they do not confer patentability on all the instantly filed claims. Applicants have amended independent claim 1 to require that Condition 1-1 and/or Condition 1-3 is satisfied; condition 1-1 being that the first amine-compound comprises two or more fluorene moieties, and condition 1-3 being that both the first and second amine-based compound comprise two or more fluorene moieties. The prior art rejection to Watabe et al. (US 2024/0324386) has been withdrawn as it was directed to Condition 1-2 which has been removed from independent claim 1. Further search has led to two new prior art rejections as described below.
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, 7-9, 19, and 21 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Nakamura et al. (US 2022/0231231, referred to as Nakamura A). The subject matter disclosed in US 2022/0231231 is fully supported in the foreign priority documents recited therein. All five of the foreign priority documents were filed before Applicants unperfected foreign priority date of 12/31/21. As such, Nakamura A qualifies as prior art under 102(a)(2).
Claim 1: Nakamura A teaches organic electroluminescent devices and display devices comprising the same. Specific device examples taught by Nakamura A satisfy all of Applicants device and structural limitations of claim 1. As one embodiment, device example 2-3 as taught in paragraphs 1188-1201 and Table 6 is drawn to a light-emitting device comprising a first electrode which is an anode (ITO), a second electrode facing the first electrode which is a cathode (Al), an interlayer between the first and second electrodes and comprising an emission layer, wherein the interlayer further comprises a hole transport region between the first electrode and the emission layer which comprises a first anode side organic layer serving as a hole injection layer (compound HT-14 and HA1), a second anode side organic layer serving as a hole transport layer (compound HT-14), a third anode side organic layer comprising a first amine-based compound (compound HT-16), and a fourth anode side organic layer comprising a second amine-based compound (compound HT-17). Compound HT-16, which is the first amine-based compound, has the structure
PNG
media_image1.png
98
194
media_image1.png
Greyscale
and comprises two fluorenyl moieties as shown. Compound HT-17, which is the second amine-based compound, has the structure
PNG
media_image2.png
198
200
media_image2.png
Greyscale
. In the hole transport region taught by Nakamura et al., the first amine-based compound comprises two fluorene moieties which satisfies Condition 1-1 of claim 1. Additionally, the hole transport layer in device example 2-3 consists of compound HT-14 and is free of a p-dopant which satisfies claim 1. Last, the first amine-based compound and the second amine-based compound are different, which satisfies claim 1.
Claim 5: The first layer in device example 2-3 consists of the first amine-based compound, which satisfies claim 5.
Claims 7 and 8: Table 23 of Nakamura A teaches that the HOMO energy level of compound HT-16 is -5.73 eV, and the HOMO energy level of compound HT-17 is -5.74 eV. These values are less than -4.50 eV as required by claims 7 and 8.
Claim 9: In compound HT-16, the fluorene moieties are 9,9-dimethylfluorenyl and 9,9-diphenylfluornyl, which both satisfy Formula A of claim 9 with X1 being a group including C
Claim 19: Claim 19 serves to further limit the optional embodiment where one or more of the fluorenyl moieties are represented by Formula B. Because this is not a requirement, Nakamura A may be properly relied upon to reject claim 19.
Claim 21: Nakamura A teaches and claims an electronic device which comprises the organic electroluminescent devices as taught therein (claim 30 of Nakamura et al.). As such, preparing an electronic apparatus which comprises the light-emitting device of independent claim 1 is at once envisaged.
Claims 11 and 13-17 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Nakamura et al. (US 2024/0423010, referred to as Nakamura B). The subject matter described below is fully supported foreign priority document JP 2021-163151, which was filed on 10/1/21. As such, Nakamura B qualifies as prior art under 102(a)(2).
Claim 11: Nakamura B teaches organic electroluminescent devices and display devices comprising the same. Specific device examples taught by Nakamura B satisfy all of Applicants device and structural limitations of claim 1. Comparative examples 1 and 2 (Table 1) of Nakamura B satisfy the light-emitting device of independent claim 1. These comparative examples are light-emitting devices which comprises a first electrode which is an anode (ITO), a second electrode facing the first electrode which is a cathode (Al), an interlayer between the first and second electrodes and comprising an emission layer, wherein the interlayer further comprises a hole transport region between the first electrode and the emission layer which comprises a first anode side organic layer serving as a hole injection layer (compound HT-1-3 and HA), a second anode side organic layer serving as a hole transport layer (compound HT-1-3), a third anode side organic layer comprising a first amine-based compound (compound HT-1-3), and a fourth anode side organic layer comprising a second amine-based compound (compound HT-2-3). Compound HT-1-3, which is the first amine-based compound, has the structure
PNG
media_image3.png
128
202
media_image3.png
Greyscale
(page 648) and comprises one fluorenyl moiety as shown. As applied to Formula 1 of claim 11, compound HT-1-3 has Ar11 equal to Formula A with X1 being a group including C, rings CY1 and CY2 being benzene rings, n11 equal to 1, L11 equal to a single bond, n12 and n13 equal to 1, L12 and L13 equal to phenylene, Ar12 and Ar13 equal to an unsubstituted dibenzofuran group (d12 and d13 are equal to zero).
Compound HT-2-3, which is the second amine-based compound, has the structure
Compound HT-2-3, which is the second amine-based compound, has the structure
PNG
media_image4.png
120
178
media_image4.png
Greyscale
(page 648) and has two fluorene moeities as shown. As applied to Formula 2 of claim 11, compound HT-2-3 has Ar21 equal to Formula A with X1 being a group including C, rings CY1 and CY2 being benzene rings, n21 equal to 1, L21 equal to a single bond, n22 equal to 1, L22 equal to a single bond, Ar22 equal to Formula A with X1 being a group including C, rings CY1 and CY2 being benzene rings, n23 equal to 1, L23 equal to phenylene, and Ar23 equal to an unsubstituted phenyl group (d23 is equal to zero).
Claim 13: Compound HT-2-3 satisfies Condition 2-2 of claim 13.
Claim 14: In compounds HT-1-3 and HT-2-3, the group represented by Formula A is a group represented by Formula A-1 with all variable assignments being described in claim 11 above.
Claim 15: Compound HT-1-3 has a group which satisfies Formula A-1-2 of claim 15 and compound HT-2-3 has a group which satisfies Formula A-1-4 and a group which satisfies Formula A-1-2 of claim 15.
Claim 16: In compound HT-1-3, L13 is a phenylene group which satisfies claim 16.
Claim 17: Compound HT-1-3 also satisfies Formula 1-1 of claim 17 above with R13 and R14 equal to phenyl and all other variable assignments being described in claim 11 above.
Claims 1, 4, 5, 7, 9, 19, and 21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Stoessel et al. (US 2016/0035992).
Claims 1, 4, 5, and 7: Example E1 of Stoessel et al. is drawn to a light-emitting device comprising an anode, a hole transport region comprising a hole injection layer consisting of compounds SpMA1 and F4T, a hole transport layer which is p-dopant free and consists of compound SpMA1, a first layer consisting of an amine-based compound (SpMA2), and a second layer consisting of a second amine-based compound1 (IC2), an a green light-emitting layer (CIE x/y 0.26/0.58), an electron transport region, and a cathode. The structure of the first amine-based SpMA1 is
PNG
media_image5.png
144
170
media_image5.png
Greyscale
(page 51) and comprises two fluorenyl moieties. The light-emitting device described in example E1 satisfies Condition 1-1 of claim 1. The device emits green light which satisfies claim 4 and the first layer consists of the first amine-based compound which satisfies claim 5. Additionally, it would be expected that SpMA1 would have a HOMO energy level of -4.50 eV or more as required by claim 7 as it is closely related to Applicants preferred compounds. A chemical compound and its properties are inseparable.
Claim 9: The fluorene moieties in compound SpMA1 satisfy Formula A with rings CY1 and CY2 being benzene rings and X1 being a group including carbon.
Claim 19: Claim 19 serves to further limit the optional embodiment where one or more of the fluorenyl moieties are represented by Formula B. Because this is not a requirement, Stoessel et al. may be properly relied upon to reject claim 19.
Claim 21: The light-emitting devices taught by Stoessel et al. are to be employed in display devices. As such, the preparation of a light-emitting apparatus from any of the device examples, including example E1, is at once envisaged, thereby satisfying claim 21.
Allowable Subject Matter
Claim 20 is allowed. Claims 6, 12, and 18 are objected to as being dependent upon a rejected base claim but would be allowable if rewritten in independent form including all the limitations of the base claim and any intervening claims. It cannot be definitively stated that the second amine-based compounds in the prior art references above would have a lowest excitation triplet energy of 2.65 eV or more as required by claim 6. Claim 12 requires that both Ar21 and Ar22 are groups which satisfy one of Formulae A-1-4 or B-1-1, which both require that the fluorenyl moiety is bonded at a specific ring carbon atom. Such bonding arrangements are not taught or fairly suggested in the prior art references above. Nakamura B does not teach that the second amine-based compound comprises a spirobifluorene-type moiety as shown in Formula 2-1.
A closely related prior art reference which cannot be used to reject any of Applicants instantly filed claims is Ha et al. (US 2022/0123218). Ha et al. teaches organic light-emitting devices which comprise a hole transport region comprising a hole injection layer, a hole transport layer, a hole adjusting layer comprising a first hole adjusting layer and a second hole adjusting layer, and a green light emitting layer (Table 2). However, the first and second hole adjusting layer, while amine-based compounds do not satisfy Condition 1-1 or 1-3 of claim 1 and they each do not comprise at least one fluorenyl moiety as required by claim 11.
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.
Information regarding the status of an application may be obtained from Patent Center. Status information for published applications may be obtained from Patent Center. Status information for unpublished applications is available through Patent Center for authorized users only. Should you have questions about access to Patent Center, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free).
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) Form at https://www.uspto.gov/patents/uspto-automated- interview-request-air-form.
/Robert S Loewe/Primary Examiner, Art Unit 1766
1 Compound IC2, in the broadest sense, is an amine-based compound. A carbazole group comprises a secondary amine nitrogen.
Prosecution Insights