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 .
Terminal Disclaimer
The terminal disclaimer filed on 02/12/2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of US Patent No. 12,369,488 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Response to Amendment
The amendment of 02/12/2026 has been entered.
Disposition of claims:
Claims 12 and 16 have been canceled.
Claims 21-22 have been added.
Claims 1-11, 13-15, 17-22 are pending.
Claims 1, 13, 15, 17, and 19-20 have been amended.
The cancellation of claims 12 and 16 obviates the rejections of claims 12 and 16 set forth in the last Office Action.
The amendments of claims 1, 13, 15, 17, and 19-20 have overcome the rejections of claims 13-14 under 35 U.S.C. 112(b), the rejection of claim 15 under 35 U.S.C. 112(b), the rejection of claim 19 under 35 U.S.C. 112(b), the rejections of claims 13-14 under 35 U.S.C. 112(d), the rejection of claim 15 under 35 U.S.C. 112(d) set forth in the last Office Action. The rejections have been withdrawn.
The approved Terminal Disclaimer of 02/12/2026 obviate the rejections of claims 1-4, 6-15, and 17-20 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 16-17, and 20 of US Patent no. 12,369,488 (hereafter Patent ‘488). The rejections are withdrawn.
The amendments of claims 1, 13, 15, 17, and 19-20 have overcome:
the rejections of claims 1-3, 5, 8-11, 13-14, and 17-18 under 35 U.S.C. 102(a)(1) as being anticipated by Wang et al. (CN 110981915 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent, hereafter Wang ‘915),
the rejection of claim 19 under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 110981915 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent) in view of in view of Kai et al. (US 2010/0187977 A1),
the rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 110981915 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent) as applied to claims 17-18 above, further in view of in view of Pang et al. (“A full-color, low-power, wearable display for mobile applications”, SPIE, 03/29/2012) set forth in the last Office Action.
The rejections have been withdrawn.
Response to Arguments
Applicant’s arguments see page 78-80 of the reply filed 02/12/2026 regarding the rejections of claims 1-3, 5, 8-10, and 13-14 under 35 U.S.C. 102(a)(1) as being anticipated by Wang ‘986, the rejections of claims 1-3, 4, 6-7, 9-10, and 13-14 under 35 U.S.C. 103 as being unpatentable over Wang ‘986/Hwang, the rejections of claims 1-3, 5-6, 8-10, and 13-15 under 35 U.S.C. 103 as being unpatentable over Wang ‘986/Kim, the rejections of claims 17-18 under 35 U.S.C. 103 as being unpatentable over Wang ‘986, the rejection of claim 19 under 35 U.S.C. 103 as being unpatentable over Wang ‘986/Kai, the rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Wang ‘986/Pang set forth in the Office Action of 11/14/2025 have been considered.
Applicant argues that the amended claims are patentable over Wang ‘986.
The cited rejections refer to Compound p59-5 (section 25 of the last Office Action) and the Compound of Wang ‘986 as modified by Hwang (section 45 of the last Office Action). Both compounds do not read on the limitation of Formula I of the amended claims; thus, the rejections are withdrawn.
However, Wang ‘986 is still applicable to make new grounds of rejection using a new teaching reference.
Wang ‘986 teaches a compound ([0046], the 2nd compound on page 59 of the original document, hereafter Compound p59-2).
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In the Compound p59-2, the aryl ring coordinating to the Ir metal enclosed by a dashed circle in the figure above is not disubstituted by two different substituents.
Takiguchi discloses an Ir complex comprising an aromatic group of Formula (5) and used for an organic light emitting device ([0034]-[0044]).
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Takiguchi exemplifies dimethyl fluorene as an example of the Formula (5) (Example 1 in [0139]).
Takiguchi teaches that incorporation of the aromatic group of Formula (5) of Takiguchi provides an ability to control emission wavelength, enhanced solubility which facilitates purification and recrystallization, suppressed thermal activation, and reduced quenching ([0085]-[0086]).
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound p59-2 of Wang ‘986 by substituting the phenyl group coordinating to the Ir metal with dimethyl fluorene as taught by Wang ‘986 and Takiguchi.
The modification provides Compound of Wang ‘986 as modified by Takiguchi.
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The left ligand of the Compound of Wang ‘986 as modified by Takiguchi has identical structure as the ligand LA of Applicant’s Formula I of the instant claims.
New grounds of rejections are applied. The amendment necessitates new grounds of rejection, making this Office Action final.
Applicant’s arguments see page 81 of the reply filed 02/12/2026 regarding the rejections of claims 1-3, 5, 8-11, 13-14, and 17-18 under 35 U.S.C. 102(a)(1) as being anticipated by Wang ‘915, the rejection of claim 19 under 35 U.S.C. 103 as being unpatentable over Wang ‘915/Kai, the rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Wang ‘915/Pang set forth in the Office Action of 11/14/2025 have been considered.
Applicant argues that the amended claims are patentable over Wang ‘915.
The cited rejections refer to Compound L035 (section 29 of the last Office Action). The compound does not read on the limitation of Formula I of the amended claims; thus, the rejections are withdrawn.
Applicant’s arguments see page 83-84 of the reply filed 02/12/2026 regarding the rejections of claim 15 under 35 U.S.C. 103 as being unpatentable over Boudreault/Kim set forth in the Office Action of 11/14/2025 have been considered.
Applicant argues that the amended claims are patentable over Boudreault.
Respectfully, the Examiner does not agree.
The claims 15 and 21 has issues of 112(b) and (d).
Claim 21 claims detailed structural formulas of the ligand LA of claim 1. However, some of the formulas are not encompassed by the Formula I of claim 1.
For example, the claim claims ligand LA2-6, having structure of
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, wherein RF is R32
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; RE is R1
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; and G is G4
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.
However, claim 1 recites “if the ring of moiety B is a monocyclic 5-membered ring, then at least one RB is a substituted aryl or heteroaryl.” The ligand LA2-6 does not have any aryl or heteroaryl at position RB; thus, the formulas are not encompassed by the Formula I.
It is unclear whether Applicant claims the structural formulas which are not encompassed by Formula I.
For the purpose of prosecution, the Examiner interprets the limitation to mean that Applicant claims the formulas regardless that the formulas are not encompassed by the Formula I of the independent claim 1.
The cited rejections refer to the Compound of Boudreault as modified by Kim (section 122 of the last Office Action).
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The compound has identical structure as Applicant’s Compound Ir(LA2-6,)2(LC17-I). Thus, the claims 15 and 21 are rejections over Boudreault ‘187 in view of Kim.
Applicant’s arguments see page 83-84 of the reply filed 02/12/2026 regarding the rejections of claims 1-4, 6-11, 13-14, 17-20 under 35 U.S.C. 103 as being unpatentable over Boudreault/Kim set forth in the Office Action of 11/14/2025 have been considered.
Applicant argues that the amended claims are patentable over Boudreault.
The cited rejections refer to the Compound of Boudreault as modified by Kim (section 122 of the last Office Action). The compound does not read on the limitation of Formula I of the amended claims; thus, the rejections are withdrawn.
However, Boudreault is still applicable to make new grounds of rejection using a new teaching reference.
Boudreault ‘187 teaches Compound 3899 ([0177]).
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In the Compound 3899, the isopropyl group at the position corresponding to R11 of the Example Formula of Boudreault ‘187 is not deuterated; however, Boudreault ‘187 does teach that R11 can be a combination of alkyl and deuterium ([0072]). Boudreault ‘187 further teaches that the substituents of the compounds of Boudreault ‘187 can be partially or fully deuterated ([0166]). Boudreault ‘187 exemplifies a partially deuterated isopropyl group, RB16,
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([0078]).
Kim teaches that substitution of hydrogen with deuterium provides lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability ([0021]-[0022]).
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound 3899 of Boudreault ‘187 by substituting the position-1 hydrogen atom of the isopropyl group at the position corresponding to R11 of the Example Formula of Boudreault ‘187 with deuterium, as taught by Boudreault ‘187 and Kim.
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The Compound of Boudreault ‘187 as modified by Kim does not have an aryl group substituted to the thiophene ring; however, Boudreault ‘187 does teach that the ligand of Boudreault ‘187 can be represented by
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(hereafter Formula X of Boudreault ‘187), wherein R12 can be an aryl ([0072]).
Choi discloses a complex of Formula 1 comprising a ligand of Formula 2 and used for an organic light emitting device ([0006]-[0033]).
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Choi teaches the compound of Choi provides high spin density, high radiative decay rate such that the organic light emitting device comprising the compound provides low voltage, high efficiency, high color purity and long lifespan ([0149], [0152], [0286]). The only difference between the Inventive compound 55 of Choi ([0141]) and the Comparative compound A of Choi (Table 3) is the phenyl group substituted to the thiophene ring at the position corresponding to R12 of the Formula X of Boudreault ‘187; thus, an ordinary skill in the art would understand the phenyl at the position provides the benefits taught by Choi.
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Boudreault ‘187 as modified by Kim by incorporating the substituted phenyl group of the Inventive compound 55 of Choi (i.e. the part enclosed by a dashed circle in the figure above) at the position corresponding to R12 of the Formula X of Boudreault ‘187 as taught by Boudreault ‘187 and Choi.
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The modification provides Compound of Boudreault ‘187 as modified by Kim and Choi, wherein the left ligand reads on Applicant’s Formula 1 of the amended claims.
New grounds of rejections are applied. The amendment necessitates new grounds of rejection, making this Office Action final.
Claim Objections
Claims 1, 17, and 20 are objected to because of the following informalities:
In claims 1, 17, and 20, Applicant recites “with the proviso that if LA has a structure … , then two RA, two RB, and RA and an RB, or an RB and an RC are joined…” It should be “with the proviso that if LA has a structure … , then two RA, two RB, an RA and an RB, or an RB and an RC are joined…” (emphasis added).
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim 10 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.
Regarding claim 10, claim 10 claims detailed structural formulas of the ligand LA of claim 1 including the following formula.
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In the formula the ring B is a monocyclic 6-membered ring. However, claim 1 recites “if the ring of moiety B fused to ring A is a 6-membered ring, then moiety B is a polycyclic fused ring system.” Thus, the formula is not encompassed by the Formula I.
It is unclear whether Applicant claims the structural formulas which are not encompassed by Formula I.
For the purpose of prosecution, the Examiner interprets the limitation to mean that Applicant claims the formulas regardless that the formulas are not encompassed by the Formula I of the independent claim 1.
Claim 11 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.
Regarding claim 11, claim 11 claims detailed structural formulas of the ligand LA of claim 1 including following formulas.
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In the formulas the ring B is benzene. However, claim 1 recites “if the ring of moiety B fused to ring A is a 6-membered ring, then moiety B is a polycyclic fused ring system.” Benzene is not a polycyclic fused ring system; thus, the formulas are not encompassed by the Formula I.
It is unclear whether Applicant claims the structural formulas which are not encompassed by Formula I.
For the purpose of prosecution, the Examiner interprets the limitation to mean that Applicant claims the formulas regardless that the formulas are not encompassed by the Formula I of the independent claim 1.
Claim 15 and 21 are 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.
Regarding claim 21, claim 21 claims detailed structural formulas of the ligand LA of claim 1. However, some of the formulas are not encompassed by the Formula I of claim 1.
For example, the claim claims ligand LA2-6, having structure of
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, wherein RF is R32
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; RE is R1
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; and G is G4
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.
However, claim 1 recites “if the ring of moiety B is a monocyclic 5-membered ring, then at least one RB is a substituted aryl or heteroaryl.” The ligand LA2-6 does not have any aryl or heteroaryl at position RB; thus, the formulas are not encompassed by the Formula I.
It is unclear whether Applicant claims the structural formulas which are not encompassed by Formula I.
For the purpose of prosecution, the Examiner interprets the limitation to mean that Applicant claims the formulas regardless that the formulas are not encompassed by the Formula I of the independent claim 1.
Regarding claim 15, claim 15 is rejected due to the dependency from claim 21.
Claim 10 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.
Regarding claim 10, claim 10 claims detailed structural formulas of the ligand LA of claim 1. However, a part of the formulas including the following formula is not encompassed by the Formula I of claim 1.
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For example, in above formula the ring B is a monocyclic 6-membered ring. However, claim 1 recites “if the ring of moiety B fused to ring A is a 6-membered ring, then moiety B is a polycyclic fused ring system.” Thus, the formula is not encompassed by the Formula I.
Currently claim 10 is dependent from claim 1. Therefore, claim 10 fails to include all the limitations of the claims upon which they depend.
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 11 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.
Regarding claim 11, claim 11 claims detailed structural formulas of the ligand LA of claim 1. However, a part of the formulas including the following formulas are not encompassed by the Formula I of claim 1.
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For example, in above formulas the ring B is benzene. However, claim 1 recites “if the ring of moiety B fused to ring A is a 6-membered ring, then moiety B is a polycyclic fused ring system.” Benzene is not a polycyclic fused ring system; thus, the formulas are not encompassed by the Formula I.
Currently claim 11 is dependent from claim 1. Therefore, claim 11 fails to include all the limitations of the claims upon which they depend.
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.
Claims 15 and 21 are 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.
Regarding claim 21, claim 21 claims detailed structural formulas of the ligand LA of claim 1. However, some of the formulas are not encompassed by the Formula I of claim 1.
For example, the claim claims ligand LA2-6, having structure of
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, wherein RF is R32
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; RE is R1
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; and G is G4
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.
However, claim 1 recites “if the ring of moiety B is a monocyclic 5-membered ring, then at least one RB is a substituted aryl or heteroaryl.” The ligand LA2-6 does not have any aryl or heteroaryl at position RB; thus, the formulas are not encompassed by the Formula I.
Currently claim 21 is dependent from claim 1. Therefore, claim 21 fails to include all the limitations of the claims upon which they depend.
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.
Regarding claim 15, claim 15 is rejected due to the dependency from claim 21.
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 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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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 1-3, 5-10, 13-14, and 17-18 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 112645986 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent) in view of Takiguchi et al. (US 2003/0068535 A1, hereafter Takiguchi).
Regarding claims 1-3, 5-10, 13-14, and 17-18, Wang ‘986 discloses a compound (Formula I) used for an organic light emitting device (page 2 under Summary of the Invention of the English translation). Wang ‘986 exemplifies a compound ([0046], the 2nd compound on page 59 of the original document, hereafter Compound p59-2).
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Wang ‘986 does not disclose a specific organic light emitting device comprising the Compound p59-2; however, Wang ‘986 does teach that the compound of Wang ‘986 can be used for an organic light emitting device (page 29). Wang ‘986 teaches the structure of an organic light emitting device comprising an anode, an emissive layer (the compound of Wang ‘986 as an emitter, a carbazole compound H-1 as a host), and a cathode (Example 1 on page 39 and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound p59-2 of Wang ‘986 by incorporating it as the emitter of the emissive layer of an organic light emitting device as taught by Wang ‘986.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of emitters of Wang ‘986 in the device of Wang ‘986 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified organic light emitting device of Wang ‘986 comprising an anode, an emissive layer (Compound p59-2 of Wang ‘986 as an emitter and a carbazole compound H-1 as a host), and a cathode, wherein the emissive layer is an organic layer.
In the Compound p59-2, the aryl ring coordinating to the Ir metal enclosed by a dashed circle in the figure above is not disubstituted by two different substituents.
Takiguchi discloses an Ir complex comprising an aromatic group of Formula (5) and used for an organic light emitting device ([0034]-[0044]).
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Takiguchi exemplifies dimethyl fluorene as an example of the Formula (5) (Example 1 in [0139]).
Takiguchi teaches that incorporation of the aromatic group of Formula (5) of Takiguchi provides an ability to control emission wavelength, enhanced solubility which facilitates purification and recrystallization, suppressed thermal activation, and reduced quenching ([0085]-[0086]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound p59-2 of Wang ‘986 by substituting the phenyl group coordinating to the Ir metal with dimethyl fluorene as taught by Wang ‘986 and Takiguchi.
The motivation of doing so would have been to provide an ability to control emission wavelength, enhanced solubility which facilitates purification and recrystallization, suppressed thermal activation, and reduced quenching based on the teaching of Takiguchi.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A).
The modification provides Compound of Wang ‘986 as modified by Takiguchi.
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The left ligand of the Compound of Wang ‘986 as modified by Takiguchi has identical structure as the ligand LA of Applicant’s Formula I of the instant claims, meeting all the limitations of claims 1-3, 5-10, and 13-14.
The modification also provides Organic light emitting device of Wang ‘986 as modified by Takiguchi comprising an anode, an emissive layer (Compound of Wang ‘986 as modified by Takiguchi as an emitter and a carbazole compound H-1 as a host), and a cathode, wherein the emissive layer is an organic layer, meeting all the limitations of claims 17-18.
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 112645986 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent) in view of Takiguchi et al. (US 2003/0068535 A1) as applied to claims 1-3, 5-10, 13-14, and 17-18 above, further in view of in view of Kai et al. (US 2010/0187977 A1, hereafter Kai).
Regarding claim 19, the Organic light emitting device of Wang ‘986 as modified by Takiguchi reads on all the features of claim 17 as outlined above.
The device comprises an anode, an emissive layer (Compound of Wang ‘986 as modified by Takiguchi as an emitter and a carbazole compound H-1 as a host), and a cathode.
The host of the device does not comprise the specific host claimed in the instant claim 19; however, Wang ‘986 does teach that the compound of Wang ‘986 can be used as the dopant with a host in the emissive layer of an organic light emitting device (page 29).
Kai discloses an organic light emitting device wherein the light emitting layer comprises a phosphorescent dopant and an indolocarbazole compound (Abstract).
Kai teaches a host compound (Compound (3) in [0038]) which is used to make the emitting layer of organic light emitting device with a phosphorescent dopant ([0039]).
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The Compound (3) of Kai has identical structure as the second compound of the HOST group of the instant claim.
Kai further teaches the compound of the invention provides remarkable improvements in luminous efficiency and driving stability to make an excellent organic electric element ([0039], [0047]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skills in the art to have modified the Organic light emitting device of Wang ‘986 as modified by Takiguchi by substituting the host with the Compound (3) of Kai in the emissive layer of the device, as taught by Wang ‘986 and Kai.
The motivation of doing so would provide the organic light emitting device with improved luminous efficiency and driving stability, based on teaching of Kai.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of hosts would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Wang ‘986 as modified by Takiguchi and Kai comprising an anode, an emissive layer (Compound of Wang ‘986 as modified by Takiguchi as an emitter and Compound (3) of Kai as a host), and a cathode, wherein the emissive layer is an organic layer.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 112645986 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent) in view of Takiguchi et al. (US 2003/0068535 A1) as applied to claims 1-3, 5-10, 13-14, and 17-18 above, further in view of in view of Pang et al. (“A full-color, low-power, wearable display for mobile applications”, SPIE, 03/29/2012, hereafter Pang).
Regarding claim 20, the Organic light emitting device of Wang ‘986 as modified by Takiguchi reads on all the features of claim 17 as outlined above.
The device comprises an anode, an emissive layer (Compound of Wang ‘986 as modified by Takiguchi as an emitter and a carbazole compound H-1 as a host), and a cathode.
Wang ‘986 does not disclose a flexible display device comprising the Organic light emitting device of Wang ‘986 as modified by Takiguchi.
Pang discloses a display device (“flexible active matrix OLED display” in Fig. 3) comprising an organic light emitting device (“C: OLED” in Fig. 3).
Pang teaches the display device provide a full-color, low-power, wearable display for mobile application (title and abstract).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Organic light emitting device of Wang ‘986 as modified by Takiguchi by incorporating it into a flexible display device, as taught by Pang.
The motivation of doing so would have been to provide a full-color, low-power, wearable display for mobile application based on the teaching of Pang.
Furthermore, the modification would have been a combination of prior art elements according to known material and method to achieve predictable results. See MPEP 2143(I)(A). The substitution of the organic light emitting devices in a flexible display device would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides a flexible display device comprising the Organic light emitting device of Wang ‘986 as modified by Takiguchi, wherein the flexible display device is a consumer product.
Claims 15 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Boudreault et al (US 2018/0097187 A1, hereafter Boudreault ‘187) in view of Kim et al. (US 2008/0194853 A1, hereafter Kim).
Regarding claims 15 and 21, Boudreault ‘187 discloses a compound comprising a ligand LA of Formula I, used as the emitter of an organic light emitting device ([0002]). Boudreault ‘187 teaches more specific ligand structure represented by Example Formula ([0072]). Boudreault ‘187 exemplifies Compound 3899 ([0177]). Boudreault ‘187 exemplifies an organic light emitting device comprising an anode, an emissive layer (a carbazole compound H as a host, and Compound 3899 as a dopant), and a cathode (Example 2 in [0197] and Tables 1-2).
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In the Compound 3899, the isopropyl group at the position corresponding to R11 of the Example Formula of Boudreault ‘187 is not deuterated; however, Boudreault ‘187 does teach that R11 can be a combination of alkyl and deuterium ([0072]). Boudreault ‘187 further teaches that the substituents of the compounds of Boudreault ‘187 can be partially or fully deuterated ([0166]). Boudreault ‘187 exemplifies a partially deuterated isopropyl group, RB16,
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([0078]).
Kim teaches that substitution of hydrogen with deuterium provides lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability ([0021]-[0022]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound 3899 of Boudreault ‘187 by substituting the position-1 hydrogen atom of the isopropyl group at the position corresponding to R11 of the Example Formula of Boudreault ‘187 with deuterium, as taught by Boudreault ‘187 and Kim.
The motivation of doing so would have been to provide lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability, based on the teaching of Kim.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of isopropyl with 1-deuterated isopropyl at the position corresponding to R11 of the Example Formula of Boudreault ‘187 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Boudreault ‘187 as modified by Kim which has identical structure as Applicant’s Compound Ir(LA2-6,)2(LC17-I), wherein LA1302-38 has general formula LAi-6
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, wherein RE is R1
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; RF is R32
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; and G is G4
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, and LC1-I has general formula LCj-I
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, wherein R201 and R202 are each RD17
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.
Claims 1-4, 6-11, 13-14, and 17-20 are rejected under 35 U.S.C. 103 as being unpatentable over Boudreault et al (US 2018/0097187 A1, hereafter Boudreault ‘187) in view of Kim et al. (US 2008/0194853 A1, hereafter Kim) and Choi et al. (US 2019/0326527, hereafter Choi).
Regarding claims 1-4, 6-11, 13-14, 17-18, and 20, Boudreault ‘187 discloses a compound comprising a ligand LA of Formula I, used as the emitter of an organic light emitting device ([0002]). Boudreault ‘187 teaches more specific ligand structure represented by Example Formula ([0072]). Boudreault ‘187 exemplifies Compound 3899 ([0177]). Boudreault ‘187 exemplifies an organic light emitting device comprising an anode, an emissive layer (a carbazole compound H as a host, and Compound 3899 as a dopant), and a cathode (Example 2 in [0197] and Tables 1-2).
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In the Compound 3899, the isopropyl group at the position corresponding to R11 of the Example Formula of Boudreault ‘187 is not deuterated; however, Boudreault ‘187 does teach that R11 can be a combination of alkyl and deuterium ([0072]). Boudreault ‘187 further teaches that the substituents of the compounds of Boudreault ‘187 can be partially or fully deuterated ([0166]). Boudreault ‘187 exemplifies a partially deuterated isopropyl group, RB16,
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([0078]).
Kim teaches that substitution of hydrogen with deuterium provides lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability ([0021]-[0022]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound 3899 of Boudreault ‘187 by substituting the position-1 hydrogen atom of the isopropyl group at the position corresponding to R11 of the Example Formula of Boudreault ‘187 with deuterium, as taught by Boudreault ‘187 and Kim.
The motivation of doing so would have been to provide lower zero point energy, lower vibration energy, decreased van der Waals force, and reduced intermolecular collision, improved efficiency and thermal stability, based on the teaching of Kim.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of isopropyl with 1-deuterated isopropyl at the position corresponding to R11 of the Example Formula of Boudreault ‘187 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Boudreault ‘187 as modified by Kim.
The modification also provides Organic light emitting device of Boudreault ‘187 as modified by Kim comprising an anode, an emissive layer (a carbazole compound H as a host, and Compound of Boudreault ‘187 as modified by Kim as a dopant), and a cathode.
The Compound of Boudreault ‘187 as modified by Kim does not have an aryl group substituted to the thiophene ring; however, Boudreault ‘187 does teach that the ligand of Boudreault ‘187 can be represented by
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(hereafter Formula X of Boudreault ‘187), wherein R12 can be an aryl ([0072]).
Choi discloses a complex of Formula 1 comprising a ligand of Formula 2 and used for an organic light emitting device ([0006]-[0033]).
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Choi teaches the compound of Choi provides high spin density, high radiative decay rate such that the organic light emitting device comprising the compound provides low voltage, high efficiency, high color purity and long lifespan ([0149], [0152], [0286]). The only difference between the Inventive compound 55 of Choi ([0141]) and the Comparative compound A of Choi (Table 3) is the phenyl group substituted to the thiophene ring at the position corresponding to R12 of the Formula X of Boudreault ‘187; thus, an ordinary skill in the art would understand the phenyl at the position provides the benefits taught by Choi.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Boudreault ‘187 as modified by Kim by incorporating the substituted phenyl group of the Inventive compound 55 of Choi (i.e. the part enclosed by a dashed circle in the figure above) at the position corresponding to R12 of the Formula X of Boudreault ‘187 as taught by Boudreault ‘187 and Choi.
The motivation of doing so would have been to provide high spin density, high radiative decay rate such that the organic light emitting device comprising the compound provides low voltage, high efficiency, high color purity and long lifespan based on the teaching of Choi.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of hydrogen with an aryl group at the position corresponding to R12 of the Formula X of Boudreault ‘187 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Boudreault ‘187 as modified by Kim and Choi, meeting all the limitations of claims 1-4, 6-11, and 13-14.
The modification also provides Organic light emitting device of Boudreault ‘187 as modified by Kim and Choi comprising an anode, an emissive layer (a carbazole compound H as a host, and Compound of Boudreault ‘187 as modified by Kim and Choi as a dopant), and a cathode, meeting all the limitations of claims 17-18.
Boudreault ‘187 in view of Kim and Choi does not disclose a specific consumer product comprising the Organic light emitting device of Boudreault ‘187 as modified by Kim and Choi; however, Boudreault ‘187 does teach a consumer product comprising the organic light emitting device of Boudreault ‘187 ([0026]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Organic light emitting device of Boudreault ‘187 as modified by Kim and Choi by incorporating it into a consumer product, as taught by Boudreault ‘187 and Kim and Choi.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides a consumer product comprising the Organic light emitting device of Boudreault ‘187 as modified by Kim and Choi, meeting all the limitations of claim 20.
Regarding claim 19, the Organic light emitting device of Boudreault ‘187 as modified by Kim and Choi reads on all the features of claim 17 as outlined above.
The host Compound H of Boudreault ‘187 is not same as any one of the HOST group of claim 19. However, Boudreault ‘187 does teach dicarbazolyl dibenzothiophene used as the host of the device of Boudreault ‘187 (the first compound in [0121]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Organic light emitting device of Boudreault ‘187 as modified by Kim and Choi by substituting the host compound with dicarbazolyl dibenzothiophene as taught by Boudreault ‘187.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification also provides Organic light emitting device of Boudreault ‘187 as modified by Kim and Choi (2) comprising an anode, an emissive layer (dicarbazolyl dibenzothiophene as a host, and Compound of Boudreault ‘187 as modified by Kim and Choi as a dopant), and a cathode.
Claims 1-3, 5-6, 8-11, 13-15, 17-18, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 111825725 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent, hereafter Wang ‘725) in view of Xia et al. (US 2010/0270916 A1, hereafter Xia).
Regarding claims 1-3, 5-6, 8-11, 13-14, and 17-18, Wang ‘725 discloses a compound (Formula I) used for an organic light emitting device (page 1 under Summary of the Invention of the English translation). Wang ‘725 exemplifies Compound I-2 ([0017], Example 6 on page 22). Wang exemplifies an organic light emitting device comprising an anode, an emissive layer (Compound I-2 as a dopant and CBP as a host), and a cathode (Example 24 on page 25 and Table 2).
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In the Compound I-2, the position-a of the terminal benzene ring corresponding to the ring substituted by R1 of Formula I of Wang ‘725 is unsubstituted (see the annotated latter “a” in the figure above); however, Wang ‘725 does teach the substituent of R1 of Formula I can be a substituted or unsubstituted C1-C10 alkyl (page 2) and exemplifies a methyl group (see examples in [0017]-[0033] including at least Compound I-44).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound I-2 of Wang ‘725 by substituting the hydrogen atom at the position-a (i.e. R1 of Formula I of Wang ‘725) with a methyl group, as taught by Wang ‘725
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of hydrogen to methyl at the position corresponding to R1 of Formula I of Wang ‘725 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides modified compound of Wang ‘725.
The modification also provides Modified organic light emitting device comprising an anode, an emissive layer (Modified compound of Wang ‘725 as a dopant and CBP as a host), and a cathode.
In the Modified compound of Wang ‘725, the methyl group at the position corresponding to R1 of Formula I of Wang is not CD3; however, Wang ‘725 does teach that the hydrogen atoms of the substituent at R1 can be replace by deuterium (page 2, line 7).
Xia discloses a metal complex comprising a ligand of Formula I and used for an organic light emitting device ([0003], [0016]).
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In the compound of Xia, one of substituents RA and RB is CD3 which can be attached to a ring conjugated or fused to the ring A or ring B of Formula I ([0019]). Xia exemplifies Compound 26, wherein CD3 is substituted to the ring conjugated or fused to the ring A ([0079]).
Xia teaches that substitution of methyl to CD3 provides increased bond strength and stability, and improved efficiency and lifetime ([0065]-[0066]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Modified compound I-2 of Wang ‘725 by substituting the methyl group at the position corresponding to the R1 of Formula I of Wang ‘725 with CD3, as taught by Wang ‘725 and Xia.
The motivation of doing so would have been to provide increased bond strength and stability, and improved efficiency and lifetime, based on the teaching of Xia.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of methyl to CD3 at the position corresponding to R1 of Formula I of Wang ‘725 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Wang ‘725 as modified by Xia, meeting all the limitations of claims 1-3, 5-6, 8-11, and 13-14.
The modification also provides Organic light emitting device of Wang ‘725 as modified by Xia comprising an anode, an emissive layer (Compound of Wang ‘725 as modified by Xia as a dopant and CBP as a host), and a cathode, meeting all the limitations of claims 17-18.
Regarding claims 15 and 21, the Compound of Wang ‘725 as modified by Xia reads on all the features of claim 1 as outlined above.
The left ligand of the compound has similar structure as the ligand LA1301-3 having structure of
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, wherein RF is R1
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; RE is R31
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; and G is
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. The only difference is that the CD3 group is required to be substituted to the position-b; however, Wang ‘725 does teach the CD3 group corresponding to R1 of Formula I of Wang ‘725 can be substituted to the position b and exemplifies several embodiments, wherein R1 is substituted to the position-b (see examples in [0017]-[0033] including at least Compound I-3). Furthermore, the compound having aCD3 group substituted to the position-b is a position isomer of the compound having a CD3 group substituted to the position-a, otherwise same.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Wang ‘725 as modified by Xia by substituting the substitution position of the CD3 group from the position-a to the position-b, as taught by Wang ‘986.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the substitution position of the CD3 group corresponding to R1 of Formula I of Wang ‘725 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Compound of Wang ‘725 as modified by Xia (2).
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Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 111825725 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent, hereafter Wang ‘725) in view of Xia et al. (US 2010/0270916 A1) as applied to claims 1-3, 5-6, 8-11, 13-15, 17-18, and 21 above, further in view of Kai et al. (US 2010/0187977 A1).
Regarding claim 19, the Organic light emitting device of Wang ‘725 as modified by Xia reads on all the features of claim 17 as outlined above.
The device comprises an anode, an emissive layer (Compound of Wang ‘725 as modified by Xia as an emitter and CBP as a host), and a cathode.
The host of the device does not comprise the specific host claimed in the instant claim 19; however, Wang ‘725 does teach that the compound of Wang ‘725 can be used as the dopant with a host in the emissive layer of an organic light emitting device (page 19).
Kai discloses an organic light emitting device wherein the light emitting layer comprises a phosphorescent dopant and an indolocarbazole compound (Abstract).
Kai teaches a host compound (Compound (3) in [0038]) which is used to make the emitting layer of organic light emitting device with a phosphorescent dopant ([0039]).
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The Compound (3) of Kai has identical structure as the second compound of the HOST group of the instant claim.
Kai further teaches the compound of the invention provides remarkable improvements in luminous efficiency and driving stability to make an excellent organic electric element ([0039], [0047]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skills in the art to have modified the Organic light emitting device of Wang ‘725 as modified by Xia by substituting the host with the Compound (3) of Kai in the emissive layer of the device, as taught by Wang ‘725 and Kai.
The motivation of doing so would provide the organic light emitting device with improved luminous efficiency and driving stability, based on teaching of Kai.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of hosts would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Wang ‘725 as modified by Xia and Kai comprising an anode, an emissive layer (Compound of Wang ‘725 as modified by Xia as an emitter and Compound (3) of Kai as a host), and a cathode, wherein the emissive layer is an organic layer.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 112645986 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent) in view of Xia et al. (US 2003/0068535 A1) as applied to claims 1-3, 5-10, 13-14, and 17-18 above, further in view of in view of Pang et al. (“A full-color, low-power, wearable display for mobile applications”, SPIE, 03/29/2012).
Regarding claim 20, the Organic light emitting device of Wang ‘725 as modified by Xia reads on all the features of claim 17 as outlined above.
The device comprises an anode, an emissive layer (Compound of Wang ‘725 as modified by Xia as an emitter and CBP as a host), and a cathode.
Wang ‘725 does not disclose a flexible display device comprising the Organic light emitting device of Wang ‘725 as modified by Xia.
Pang discloses a display device (“flexible active matrix OLED display” in Fig. 3) comprising an organic light emitting device (“C: OLED” in Fig. 3).
Pang teaches the display device provide a full-color, low-power, wearable display for mobile application (title and abstract).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Organic light emitting device of Wang ‘725 as modified by Xia by incorporating it into a flexible display device, as taught by Pang.
The motivation of doing so would have been to provide a full-color, low-power, wearable display for mobile application based on the teaching of Pang.
Furthermore, the modification would have been a combination of prior art elements according to known material and method to achieve predictable results. See MPEP 2143(I)(A). The substitution of the organic light emitting devices in a flexible display device would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides a flexible display device comprising the Organic light emitting device of Wang ‘725 as modified by Xia, wherein the flexible display device is a consumer product.
Claim 22 is rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 111825725 A, the original document is referred to for figures and tables, and the English translation is referred to for the remainder body of the patent, hereafter Wang ‘725) in view of Xia et al. (US 2010/0270916 A1) as applied to claims 1-3, 5-6, 8-11, 13-15, 17-18, and 21 above, further in view of Boudreault et al. (US 2015/0001472 A1, hereafter Boudreault ‘472).
Regarding claim 22, the Compound of Wang ‘725 as modified by Xia reads on all the features of claim 1 as outlined above.
The compound has similar structure as the first compound of claim 22. The only difference is that the methyl groups of the acetylacetone ligand (i.e. the methyl at the positions corresponding to R6 and R7 of Wang ‘725) are requires to be pentyl; however, Wang ‘725 does teach R6 and R7 can be a C1-C10 alkyl group (page 2).
Boudreault ‘472 discloses a compound having acetylacetonate ligand and used for an organic light emitting device ([0002], [0015]).
Boudreault ‘472 teaches that incorporation of the ligand of Boudreault ‘472 provides narrow the emission spectrum, decreased evaporation temperature, improved efficiency ([0017]).
Boudreault ’472 exemplifies ligand LA1
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([0041]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Wang ‘725 as modified by Xia by substituting the acetylacetonate ligand with the ligand LA1 of Boudreault ‘472, as taught by Wang ‘725 and Boudreault ‘472.
The motivation of doing so would have been to provides narrow the emission spectrum, decreased evaporation temperature, improved efficiency based on the teaching of Boudreault ‘472.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the methyl group at the positions corresponding to R6 and R7 of Formula I of Wang ‘725 with a pentyl group would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Compound of Wang ‘725 as modified by Xia and Boudreault ‘472 which has identical structure as the first compound of claim 22.
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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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SEOKMIN JEON whose telephone number is (571)272-4599. The examiner can normally be reached Monday - Friday 8:30am to 5:00pm EST.
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/SEOKMIN JEON/Primary Examiner, Art Unit 1786
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