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 .
Foreign Priority
Acknowledgment is made of applicant's claim for foreign priority based on an application JP2022-065500 filed in Japan on April 12, 2022.
Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)- (d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e). Failure to provide a certified translation may result in no benefit being accorded for the non-English application.
Information Disclosure Statement
The references provided in the Information Disclosure Statements filed on February 14, 2024, June 13, 2024, October 15, 2024, April 9, 2025, and October 27, 2025, have been considered. A signed copy of the corresponding 1449 form has been included with this office action.
Status of Claims
This action is in reply to the communication filed November 1, 2023.
Claims 1-23 are currently pending and have been examined.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 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.
Claims 1, 3-7, and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wang et al. (CN113636943A, relying on WIPO English Machine Translation attached in correspondence with this office action).
Regarding claim 1, Wang et al. discloses a triarylamine compound of Formula 1
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used in organic electroluminescent display devices as a hole transporting material which provide high mobility to improve the binding force between molecules to reduce the crystallization phenomenon and improve the luminous efficiency and stability of OLEDs (Page 002, first paragraph). Wang teaches:
Compound 12 (Page 003), represented by the claimed formula (1)
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where in the claimed formula (1)
R1 to R4 are each a hydrogen atom
L1, L3, and L4 are each a single bond
L2 is an unsubstituted arylene
Ar1 is an unsubstituted aryl group having 6 ring carbon atoms
Ar2 is a substituted heterocyclic group having 5 ring atoms
X1 is S
m and n are each 0
R31 is bonded to a
R32 is bonded to b
R33 to R35, R37 to R38, and R41 to R44 are each a hydrogen atom
R36 is a single bond to 4*
Regarding claim 3, Wang further teaches where in Compound 12 m is 0.
Regarding claim 4, Wang further teaches where in Compound 12 n is 0.
Regarding claim 5, Wang further teaches where in Compound 12 Ar1 is an unsubstituted aryl group having 6 ring carbon atoms and Ar2 is a substituted heterocyclic group having 5 ring atoms.
Regarding claim 6, Wang further teaches where in Compound 12 L4 is a single bond.
Regarding claim 7, Wang further teaches where in Compound 12 L3 is a single bond.
Regarding claim 11, Wang further teaches where in Compound 12 R1 to R4 are each a hydrogen atom.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 2, 8-10, 13-20, and 23 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN113636943A, relying on WIPO English Machine Translation attached in correspondence with this office action).
Regarding claim 2, Wang et al. teaches the compound represented by formula (1) according to claim 1 as described above in Paragraph 10.
Compound 12
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of Wang does not specifically teach wherein X1 of formula (x)
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is oxygen.
However, Compound 12 of Wang is a specific compound of Formula 1
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wherein X15 is
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(Page 002). Wang teaches that X may be O.
Therefore, given the general formula and teachings of Wang, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the S atom of Compound 12 with an O atom. The substitution would have been one preferred element for another and one of ordinary skill in the art would reasonably expect the predictable result that the modified compound would be useful as hole transporting material in the hole transport layer of the device of Wang and possess the benefits taught by Wang. See MPEP 2143.I.(B).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify Compound 12 of Wang, because it would have been choosing an O atom in place of a S atom, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the hole transporting material in the hole transport layer of the device of Wang and possessing the benefits taught by Wang. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 1 of Wang having the benefits taught by Wang in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Modified Compound 12, referred to as Compound 12-1 from now on,
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reads on the instant claim wherein X1 is Oxygen.
Regarding claim 8, Wang teaches wherein:
Compound 12
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Ar1 is formula (1a)
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where in the claimed formula (1a):
k and l are each 0
k + l is 0
R111 to R115 are each a hydrogen atom
Compound 12
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of Wang does not specifically teach wherein Ar2 is a formula of (1a) to (1e). However, Compound 12 is a specific compound of Formula 1
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wherein A2 is
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. Wang teaches that A2 may also be
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. Compound 40
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is an example of specific compound of Formula 1 of Wang wherein A2 is
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.
Therefore, given the general formula and teachings of Wang, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the A2 position with a biphenyl. The substitution would have been one preferred element for another and one of ordinary skill in the art would reasonably expect the predictable result that the modified compound would be useful as hole transporting material in the hole transport layer of the device of Wang and possess the benefits taught by Wang. See MPEP 2143.I.(B).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the A2 position of Wang, because it would have been choosing a biphenyl group, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the hole transporting material in the hole transport layer of the device of Wang and possessing the benefits taught by Wang. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 1 having the benefits taught by Wang in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Modified Compound 12, referred to as Compound 12-2 from now on,
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reads on the instant claim where Ar2 is formula (1a)
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where in the claimed formula (1a):
k and l are each 0
k + l is 0
R111 to R115 are each a hydrogen atom
Regarding claim 9, modified Wang teaches wherein Ar1 and Ar2 are each formula (1a) as described above for claim 8 in Paragraph 23.
Regarding claim 10, Wang teaches that the compound according to 1 as described above for claim 1 in Paragraph 10.
Compound 12
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of Wang does not specifically teach wherein R32 or R37 is a single bond bonded to *4. However, Compound 12 is a specific compound of Formula 1
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wherein X15 is
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(Page 002), thus the bond from X15 to the corresponding carbon is a variable bond.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the bonding of X15 to the corresponding carbon so that the bonding pattern would be para- to the sulfur, because it would have been choosing the para- position over the meta- position, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the hole transporting material in the hole transporting layer of the device of Wang and possessing the benefits taught by Wang. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 1 of Wang having the benefits taught by Wang 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 12, referred to as Compound 12-3 from now on,
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reads on the claim formula wherein R37 is a single bond bonded to *4.
Regarding claim 13, Wang teaches that the triarylamine compounds of Formula 1
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are used in organic electroluminescent display devices as a hole transporting material (Page 002, first paragraph). In Device Example 1 (Depicted 1, See Fig. 1 below), Wang teaches that compound 1 of Formula 1 is used to form the hole transport layer 105 (Page 006, Device Example 1, Fig. 1). Therefore, Wang teaches a material for organic electroluminescent devices (hole transport layer is considered the material). Additionally, since Wang teaches that Compound 12 is a compound of Formula 1, it would have been obvious to one of ordinary skill in the art before the effecting filing day of the claimed invention to utilize Compound 12 as the compound of the material of the organic electroluminescent device of Wang.
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Regarding claim 14, Wang further teaches a hole transporting layer 105 comprising the compound according to claim 1 as described above for claim 13 in Paragraph 26.
Regarding claim 15, Wang further teaches an organic electroluminescent device (Device Example 1, Fig. 1 above for claim 13 in Paragraph 26) comprising:
a cathode (Fig. 1, 109),
an anode (Fig. 1, 102),
and an organic layer between the cathode and the anode (Fig. 1, 103 to 108),
wherein the organic layer comprises a light emitting layer (Fig. 1, 106),
and at least one layer of the organic layer comprises the compound according to claim 1 (Fig. 1, 105, as described above for claim 13 in Paragraph 26).
Regarding claim 16, Wang further teaches wherein the organic layer according to claim 15 comprises a hole transporting zone between the anode and the light emitting layer (Fig. 1, 103 to 105, since “hole transporting zone” is interpreted as a combination of hole injection layers and hole transporting layers in a device), and wherein the hole transporting zone contains the compound (Compound 12 is in 105, as described above for claim 13 in Paragraph 26).
Regarding claim 17, applicant does not specify composition of a first- or second-hole transporting layer or if they are different layers. Therefore, examiner interprets Wang’s hole transporting layer 105 as two sublayers of a hole transporting layer. The bottom sublayer is considered the first hole transporting layer on an anode side, and the top sublayer is considered the second hole transporting layer on the cathode side. Since Wang’s hole transporting layer 105 includes Compound 12 (as described above for claim 13 in Paragraph 26), Wang further teaches wherein both of the first hole transporting layer, and the second hole transporting layer contain Compound 12.
Regarding claim 18, Wang further teaches wherein the light emitting layer (Fig. 1, 106) and the second hole transporting layer (Fig. 1, top sublayer of 105) are in direct contact with each other (See Fig. 1).
Regarding claim 19, Wang further teaches wherein a total thickness of the first hole transporting layer, and the second hole transporting layer is 100 nm (falling within the range of 30 nm to 120 nm).
Regarding claim 20, Wang further teaches wherein the light emitting layer is a single layer (Fig. 1, 106).
Regarding claim 23, since an OLED is considered an electronic instrument, Wang further teaches an electronic instrument comprising the organic electroluminescent device according to claim 15.
Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN113636943A, relying on WIPO English Machine Translation attached in correspondence with this office action) as applied to claim 1 above, and further in view of Fennimore et al. (US 2017/0200893 A1).
Regarding claim 12, Wang et al. teaches the compound represented by formula (1) according to claim 1 as described above in Paragraph 10.
Compound 12
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of Wang does not specifically teach wherein the compound comprises at least on deuterium atom. However, Wang teaches that X11 to X14 of Formula 1 may be deuterium (Page 002, paragraph below Formula 1 structure) and "substituted or unsubstituted" means substituted with one or more substituents and one of those substituents may be deuterium (Page 002, last paragraph).
Fennimore et al. discloses an OLED device and teaches that deuterated materials can be less susceptible to degradation by holes, electrons, excitons, or a combination thereof (para. 0098). Additionally, Fennimore teaches that deuteration can potentially inhibit degradation of the compound during device operation, which in turn can lead to improved device lifetime (para. 0098).
Therefore, it would have been obvious for one of ordinary skill in the art before the effective filling date of the claimed invention to modify Compound 12 by deuterating the compound, based on the teachings of Fennimore.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to deuterate Compound 12, because it would have been choosing deuterium as a substituent, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the hole transporting material in the hole transport layer of the device of Wang and possessing the benefits taught by Fennimore. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula comprising deuterium having the benefits of stable compounds to prevent degradation and improve lifetime taught by Fennimore in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Claims 21 and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN113636943A, relying on WIPO English Machine Translation attached in correspondence with this office action) in view of. Poriel et al. is used as evidentiary reference for claim 21, Adv. Funct. Mater. 2020, 30, 1910040.
Regarding claim 21, Wang et al. teaches the organic electroluminescent device according to claim 15 as described above in Paragraph 28.
Wang does not specifically teach wherein the light emitting layer comprises a light emitting compound that shows fluorescence emission with a main peak wavelength of 500 nm or less. However, Wang teaches that the triarylamine compound may be used in a device that emits blue light (Page 006, paragraph above Device Example 1).
Osaka et al. also teaches a triarylamine derivative with hole transporting properties (abstract). Osaka teaches that the triarylamine derivative has a wide energy gap that is preferably used as a material for a light-emitting element emitting blue light (para. 0050). Osaka teaches that when the triarylamine derivative is used in a device, high color purity for blue light emission can be obtained (para. 0120).
Osaka teaches a device with a hole transporting layer 112 with the triarylamine derivative (para. 0115), and a light-emitting layer 113 with light emitting materials dopants that may be fluorescent (para. 0117). An example of a fluorescent material for the light emitting layer is YGA2S (para. 0118). Paragraph 0566 of the instant specification states that YGA2S is an example of a blue fluorescent material. The blue fluorescent material of Osaka is interpreted as the claimed light emitting compound with a fluorescence emission with a main peak wavelength of 500 nm or less as blue fluorescent compounds are considered to show a fluorescence emission with a peak wavelength below 500 nm. Furthermore, Poriel teaches that a common property of blue emitting materials is that blue light emission is between 380 nm and 500 nm with a maximum wavelength around 450 nm (Page 2, second paragraph).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the device of Wang by providing the blue emitting layer of Osaka motivated by the desire of a high color purity blue emission in the device.
Regarding claim 22, modified Wang further teaches wherein the light emitting layer comprises a phosphorescent dopant material (Osaka teaches that the dopant may also be a phosphorescent compound (para. 0117) and an example of the phosphorescent compound is Flr6. Paragraph 0569 of instant specification states that Flr6 is an example of a blue phosphorescent compound).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ADRIANA P CLAUDIO VAZQUEZ whose telephone number is (571)272-9677. The examiner can normally be reached Monday to Friday 8:30 AM - 5:30 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Marla McConnell can be reached at (571)270-7692. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ADRIANA P CLAUDIO-VAZQUEZ/Examiner, Art Unit 1789
/MARLA D MCCONNELL/Supervisory Patent Examiner, Art Unit 1789
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