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 .
Summary of Claims
Claims 1, 8, and 20-21 are amended, claims 17-19 are cancelled, and claims 22-24 are new due to Applicant's amendment dated 01/30/2026. Claims 1-2, 4-16, and 20-24 are pending.
Response to Amendment
The rejections of claims 17-19 as set forth in the previous Office Action are moot because claims 17-19 are cancelled due to the Applicant's amendment dated 01/30/2026.
The rejection of claims 1-2, 4-15, and 20-21 under 35 U.S.C. 103 as being unpatentable over Dong (English translation of CN 1093363834 A obtained from Global Dossier) in view of Lee (US 2014/0117329 A1), Shi (US 2002/0057050 A1), and Chen (US 6,380,564 B1) is overcome due to the Applicant’s amendment dated 01/30/2026. The rejection is withdrawn.
The rejection of claim 16 under 35 U.S.C. 103 as being unpatentable over Dong in view of Lee, Shi, Chen, and Lee ‘289 (US 2017/0317289 A1) is overcome due to the Applicant’s amendment dated 01/30/2026. The rejection is withdrawn.
Response to Arguments
Applicant’s arguments on pages 23-24 of the reply dated 01/30/2026 with respect to the rejection of claims 1-2, 4-16, and 20 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –Applicant argues on page 23 that the cited references fail to teach claim 1 as amended which requires the anode to consist of a metal oxide, wherein a metal of the metal oxide is tungsten, copper, or any combination thereof. Additionally, Applicant argues on page 24 that the cited references fail to teach claims 20-21 as amended which require Ar2 to be one of Formulae 2a to 2d.
Examiner's response –As discussed in greater detail in the rejection below, with respect to the amended claim 1, the newly cited reference Matsuura (US 2008/0136339 A1) teaches WO3 is a suitable substitute for ITO in an anode in an organic light emitting device. With respect to the amended claims 20-21, the newly cited reference Hong (US 2020/0212311 A1) teaches compound C-116 which reads on the claimed Formula 3 wherein Ar2 is Formula 2a, and the newly cited reference Li (English translation of CN 108203406 A obtained from Global Dossier) teaches compound B-6 which reads on the claimed Formula 4 wherein Ar2 is Formula 2a. Accordingly, the cited references teach the claims as amended.
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.
(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 20 and 23 are rejected under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Hong (US 2020/0212311 A1).
Regarding claims 20 and 23, Hong teaches an organic electroluminescent compound represented by formula 1 wherein examples thereof include compound C-116 (¶ [0008]; structure on pg. 24).
Compound C-116 is reproduced below in comparison to the claimed Formula 3 (claim 20).
C-116:
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Formula 3:
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Compound C-116 reads on the claimed Formula 3 wherein:
Ar1 is an unsubstituted C6 aryl group;
R1 and R3 to R4 are each hydrogen, and R2 is -N(Q1)(Q2);
Ar2 is represented by Formula 2a;
Z1 is hydrogen and Z2 to Z6 are not required to be present (claim 23);
b1 is 5 and b2 to b6 are not required to be present;
Ar3 and Ar4 are each an unsubstituted C6 aryl group;
L1 is a single bond;
m is 1;
a1 is 4, a2 is 1, a3 is 3, and a4 is 6;
R10a is not required to be present; and
Q1 and Q2 are each an unsubstituted C6 carbocyclic group.
Claims 21 and 24 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Li (English translation of CN 108203406 A obtained from Global Dossier).
Regarding claims 21 and 24, Li teaches a benzofluorene organic electroluminescent material represented by formula (1) wherein examples thereof include compound B-6 (beginning of pg. 2; structure on pg. 7).
Compound B-6 is reproduced below in comparison to the claimed Formula 4 (claim 21).
B-6:
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Formula 4:
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Compound B-6 reads on the claimed Formula 4 wherein:
Ar1 is an unsubstituted C6 aryl group;
R1 to R3 are each hydrogen and R4 is an unsubstituted C5 heteroaryl group;
Ar2 is represented by Formula 2a;
Z1 is hydrogen and Z2 to Z6 are not required to be present (claim 24);
b1 is 5 and b2 to b6 are not required to be present;
Ar3 and Ar4 are each an unsubstituted C6 aryl group;
L1 is a single bond;
m is 1;
a1 is 4, a2 and a3 are each 3, and a4 is 1; and
R10a is not required to be present.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-2, 4-15, and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Dong (English translation of CN109336834 A obtained from Global Dossier) in view of in view of Lee (US 2014/0117329 A1) and Matsuura (US 2008/0136339 A1).
Regarding claims 1-2, 4-15, and 22, Dong teaches an organic electroluminescent device including an arylamine derivative represented by Formula I, wherein the arylamine derivative has good hole transport capacity, good film-forming property, good thermal stability, and provides the device with good luminous efficiency and lifetime performance (bottom of pg. 1 and beginning of pg. 2). Dong teaches the device preferably has a structure of an ITO anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode, wherein the hole transport layer includes the arylamine derivative represented by Formula I (bottom of pg. 13 and beginning of pg. 14). Examples of compounds represented by Formula I include compounds 124, 164, and 184 (pgs. 5-7).
Formula I:
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124:
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164:
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123
158
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184:
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159
149
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Compounds 124, 164, and 184 fail to read on the claimed Formula 1 wherein Ar3 and Ar4 are each a C6-C60 aryl group. However, Dong does teach in Formula I R1 to R4 may each be a C6-C30 aryl group, among others (beginning of pg. 2). As shown in compound 145, examples of the C6-C60 aryl group include unsubstituted phenyl (pg. 6).
145:
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Lee teaches amine-based compounds represented by Formula 1, wherein the amine-based compounds are used in a hole transport layer of an organic light-emitting device (¶ [0009] and [0049]). Since the substituents Ar1 and Ar2 of the fluorene are each an aryl group (as opposed to methyl groups), the amine-based compound obtains improved thermal stability and thus provides a device with low driving voltage, high efficiency, high luminance, and long lifetime (¶ [0046]-[0047]; and see Compounds 1 and 3 vs. Compound A in Table 1 on pg. 44).
Formula 1:
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210
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Therefore, in compound 124 (and alternatively, compounds 164 or 184), it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the methyl substituents with phenyl substituents in each of the fluorene-based groups, based on the teaching of Lee. The motivation for doing so would have been to provide a compound with improved thermal stability and provide a device with improved driving voltage, luminance, efficiency, and lifespan, as taught by Lee.
The modified compound 124 is reproduced below in comparison to the claimed Formula 1.
modified 124:
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526
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Formula 1:
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The modified compound 124 reads on the claimed Formula 1 and Formula 3 (claims 1 and 14) wherein:
A1 is an unsubstituted bicyclic aromatic moiety of naphthalene (claim 4);
Ar1 and Ar3 and Ar3 are each an unsubstituted C6 aryl group represented by Formula 2a wherein Z1 is hydrogen, Ar2 is a C6 aryl group substituted with one R10a and is represented by Formula 2a wherein Z1 is a C13 aryl group (claims 9 and 12);
R1 to R3 are each hydrogen (claim 10);
L1 is a single bond (claim 11);
m is an integer of 1;
a1 is an integer of 4, and a2 and a3 are each an integer of 3; and
Ra is a C13 carbocyclic group further substituted with two C6 carbocyclic groups.
Alternatively, the modified compound 164 is reproduced below in comparison to the claimed Formula 1.
modified 164:
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Formula 1:
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The modified compound 164 reads on the claimed Formula 1 and Formula 2 (claims 1 and 13) wherein:
A1 is an unsubstituted bicyclic aromatic moiety of naphthalene (claim 4);
Ar1 is an unsubstituted C6 aryl group, Ar2 is a C13 aryl group substituted with twoR10a, and Ar3 and Ar3 are each an unsubstituted C6 aryl group (claim 9);
R1 to R3 are each hydrogen (claim 10);
L1 is a single bond (claim 11);
m is an integer of 1;
a1 is an integer of 4, and a2 and a3 are each an integer of 3; and
each Ra is an unsubstituted C6 carbocyclic group.
Alternatively, the modified compound 184 is reproduced below in comparison to the claimed Formula 1.
modified 184:
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Formula 1:
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The modified compound 184 reads on the claimed Formula 1 and Formula 4 (claims 1 and 15) wherein:
A1 is an unsubstituted bicyclic aromatic moiety of naphthalene (claim 4);
Ar1 is an unsubstituted C6 aryl group, Ar2 is a C13 aryl group substituted with two R10a, and Ar3 and Ar3 are each an unsubstituted C6 aryl group (claim 9);
R1 to R3 are each hydrogen (claim 10);
L1 is a single bond (claim 11);
m is an integer of 1;
a1 is an integer of 4, and a2 and a3 are each an integer of 3; and
each Ra is an unsubstituted C6 carbocyclic group.
As discussed above, the device of Dong comprises an anode consisting of ITO (beginning of pg. 14). However, Dong fails to teach an anode consisting of a metal oxide wherein the metal is tungsten or copper.
Matsuura teaches the upper electrode (anode) of an organic EL display device may be made of IZO, ITO, or WO3 (abstract; ¶ [0020] and [0053]). Accordingly, Matsuura teaches WO3 is a suitable substitute for ITO in an anode of an organic EL display device.
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the anode consisting of ITO with an anode consisting of WO3 because Matsuura teaches WO3 is a suitable substitute for ITO in an anode of an organic EL display device. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the anode would be useful in the device of Dong. See MPEP 2143.I.(B).
Additionally, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select WO3, because it would have been choosing from a list of suitable materials for an anode taught by Matsuura, and this have been a choice from a finite number of identified, predictable solutions of a material for the anode of the device of Dong. One of ordinary skill in the art would have been motivated to produce additional devices comprising anodes having the materials taught by Matsuura in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
While Matsuura is silent as to the work function value of WO3, the instant specification recites WO3 is an example of a metal oxide having a work function value of -5.3 eV or less (instant ¶ [0061] and [0067]) (claim 8).
Per claim 6, the device includes an anode, a hole injection layer, and a hole transporting layer including the modified compound 124 (or alternatively, the modified compounds 164 or 184). Accordingly, the hole transporting layer is in electrical contact with the anode.
Per claim 7, the device of Dong in view of Lee and Matsuura does not comprise a p-dopant (see Dong, beginning of pg. 14).
Per claim 22, the metal of WO3 is tungsten.
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Dong (English translation of CN109336834 A obtained from Global Dossier) in view of in view of Lee (US 2014/0117329 A1) and Matsuura (US 2008/0136339 A1) as applied to claim 1 above, and further in view of Lee ‘289 (US 2017/0317289 A1).
Regarding claim 16, Dong in view of Lee and Matsuura teach the organic electroluminescent device comprising the modified compound 184 in the hole transport layer, as described above with respect to claim 1.
modified 184:
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Formula I:
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The modified compound 184 fails to read on a claimed compound as it comprises a fluorene group in the location of the claimed Ar2. However, Dong does teach in Formula I that n is an integer from 0 to 2 and p is an integer from 0 to 2 (see beginning of pg. 2). Thus, the compound of Dong’s Formula I is not required to contain two fluorene-based groups. Additionally, Dong teaches Ar may be selected from groups including carbazole and dibenzofuran (see beginning of pg. 2).
Lee ‘289 teaches a composition for a hole transport layer composed of two or more compounds represented by Formula 1, wherein the composition improves the luminous efficiency, stability, and lifespan of a display device (abstract; ¶ [0009]-[0010]). One of the two compounds contains all C6 to C24 aryl groups in the location of Ar1, Ar2, and Ar3 and the remaining one kind of compound contains dibenzofuran or dibenzothiophene in at least one of Ar1, Ar2, and Ar3. When one of the compounds contains dibenzofuran (for example, compound 1-52’), the mixture exhibits higher efficiency and lifespan than compounds comprising only aryl groups (¶ [0105]; see structure on pg. 11).
Formula 1:
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1-52’:
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Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to further include in the hole transport layer a compound represented by Formula 1 of Lee ‘289 in which Ar1, Ar2, and Ar3 are all C6 to C24 aryl groups, and to substitute a group on the modified compound 184 with dibenzofuran (as shown in compound 1-52’) to arrive at a composition containing two compounds represented by Formula 1 wherein one of the two compounds contains dibenzofuran, based on the teaching of Lee ‘289. The motivation for doing so would have been to improve luminous efficiency, stability, and lifespan, as taught by Lee ‘289.
In particular, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the fluorenyl group of the modified compound 184 with dibenzofuran, because it would have been choosing one of three groups of the modified compound 184 in which to substitute with dibenzofuran. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Dong’s Formula I and comprising dibenzofuran having the benefits taught by Lee ‘289 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 184 reads on Dong’s Formula I wherein: L1 to L3 are each a single bond; A is a C12 fused aryl; B, R3, and R4 are not required to be present; R1 and R2 are each an unsubstituted C6 aryl group; m is an integer of 1, n is an integer of 0, and p is an integer of 2; one instance of Ar is carbazole and one instance of Ar is dibenzofuran (see Dong, beginning of pg. 2). Accordingly, the modified compound 184 is expected to obtain the benefits of Dong.
The modified compound 184 reads on the claimed compound 28.
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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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BRAELYN R WATSON whose telephone number is (571)272-1822. The examiner can normally be reached M-F 7:30am-5pm.
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/BRAELYN R WATSON/Examiner, Art Unit 1786