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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 05/06/2026 has been entered.
Summary of Claims
Claims 1, 12, 22-23, and 28 are amended due to Applicant's amendment dated 05/06/2026. Claims 1-28 are pending.
Response to Amendment
The rejection of claims 12 and 28 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 as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 05/06/2026. The rejection is withdrawn.
The rejection of claims 12 and 28 under 35 U.S.C. 112(d) or 35 U.S.C. 112 (pre-AIA ), 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 as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 05/06/2026. The rejection is withdrawn.
The rejection of claims 11 and 27 under 35 U.S.C. 103 as being unpatentable over Dong (English translation of CN 110845394 A obtained from Global Dossier) in view of Jeong (US 2019/001666 A1) is overcome due to the Applicant’s amendment dated 05/06/2026. The rejection is withdrawn.
The rejection of claims 1-3, 7-10, 12-13, 18, 22, 25-26, and 28 under 35 U.S.C. 103 as being unpatentable over Watabe (US 2021/0005814 A1) in view of Ma (US 2022/0306567 A1) is withdrawn due to reconsideration of the original grounds of rejection.
The rejection of claims 4, 6, and 23 under 35 U.S.C. 103 as being unpatentable over Watabe in view of Ma and Ma ‘273 (US 2023/0272273 A1) is withdrawn due to reconsideration of the original grounds of rejection.
The rejection of claims 5, 12, 24, and 28 under 35 U.S.C. 103 as being unpatentable over Watabe in view of Ma and Wang (English translation of CN 112010759 obtained from Global Dossier) is withdrawn due to reconsideration of the original grounds of rejection.
The rejection of claims 14 and 19 under 35 U.S.C. 103 as being unpatentable over Watabe in view of Ma and Hwang (US 2008/0286606 A1) is withdrawn due to reconsideration of the original grounds of rejection.
The rejection of claims 15-17 under 35 U.S.C. 103 as being unpatentable over Watabe in view of Ma and Lee (US 2014/0117329 A1) is withdrawn due to reconsideration of the original grounds of rejection.
The rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Watabe in view of Ma, Hwang, and Lee ‘919 (US 2017/0330919 A1) is withdrawn due to reconsideration of the original grounds of rejection.
The rejection of claim 21 under 35 U.S.C. 103 as being unpatentable over Watabe in view of Ma, Hwang, and Shitagaki (US 2009/0102368 A1) is withdrawn due to reconsideration of the original grounds of rejection.
The rejection of claims 1-3, 6-13, 15-18, 22, and 25-28 on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of US 12,497,348 B2 is not overcome due to the Applicant’s amendment dated 05/06/2026. The rejection is maintained.
Response to Arguments
Applicant’s arguments on pages 145-156 of the reply dated 05/06/2026 with respect to the rejection of claims 1-28 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –On pages 145-147, Applicant argues the cited references fail to read on the claims as amended which require when at least one of C1 and C2 is a substituted or unsubstituted bicycloheptanyl group, M is represented by Formula 1-a or 1-b.
Examiner's response –As discussed in greater detail in the rejection below, the cited references teach the claims as amended.
Applicant's argument –On pages 147-156, Applicant argues compounds of the instant application show unexpected results with respect to driving voltage, luminance, efficiency, and life over the cited compound of Watabe. In particular, Applicant argues the claimed embodiments (such as Example 23 using Compound 1015) exhibit unexpected results over Comparative Example 3 using Comparative Compound C4, which is identical to Watabe’s compound 100. Applicant argues that the improvement is due to Compound 1015 comprising a cyclohexane group in the C1 position and a bicycloheptanyl group in the C2 position, whereas Comparative Compound C4 comprises a cyclohexane group in both the C1 and C2 positions.
Examiner's response –Overcoming a rejection based on unexpected results requires at least the combination of three different elements: (i) the results must fairly compare with the closest prior art in an affidavit or declaration under 37 CFR 1.132, (ii) the claims must be commensurate in scope, and (iii) the results must truly be unexpected. MPEP 716.02. Additionally, the burden rests with Applicant to establish the results are unexpected and significant. MPEP 716.02(b).
Comparison with closest prior art
Applicant has not made a comparison to the closest prior art. The device examples of the instant specification comprise different materials than the devices of the newly cited reference Fuchiwaki (US 2018/0019416 A1).
For example, as shown below, Fuchiwaki teaches compound 64 (see structure on pg. 20 of Fuchiwaki). The closest inventive compounds to Fuchiwaki’s compound 64 are inventive compounds 873, 876, and 881 (see instant pgs. 200-201).
64:
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873:
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876:
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881:
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As shown by the structures above, Fuchiwaki’s compound 64 comprises unsubstituted triphenylsilyl groups in each of the locations C1 and C2 whereas the inventive compounds only comprise an unsubstituted triphenylsilyl group in the location of C1. Additionally, Fuchiwaki’s compound 64 comprises an unsubstituted phenyl group in the location of La and reads on the claimed Formula 1 wherein M is represented by Formula 1-c. In contrast, the inventive compounds each comprise a direct linkage in the location of La and read on the claimed Formula 1 wherein M is represented by Formula 1-a. As no explanation is provided for compounds having these differences, it is unclear if a comparison between Fuchiwaki’s compound and the inventive compounds would obtain the same results discussed by Applicant. Accordingly, a comparison of the closest prior art has not been made.
Commensurate in Scope
As discussed below, Fuchiwaki’s compound 64 includes unsubstituted triphenylsiyl groups in the locations of the claimed C1 and C2, and reads on the claimed Formula 1 wherein M is represented by Formula 1-c. These are within the scope of the claims. As there are no results comprising the structures of the prior art, it is unclear if the same results discussed by Applicant would be present.
Additionally, the data shown in Table 1 of the remarks is not commensurate in scope with the claimed invention for at least the reasons that the data is shown for the use of a compound in the hole transport layer of a device, whereas claims 22-28 are directed to a compound. The improved properties with respect to driving voltage, luminance, efficiency, and life are shown when the compound is used in a hole transport layer of an OLED, wherein the OLED has a specific structure and adjacent layers comprise specific materials. None of these limitations are required by the claim. No evidence has been provided to show that the unexpected results would be present for the use of the compound in other layers.
Unexpected Results
It should be noted that even if the above issues are addressed, it is unclear whether the improvement shown between Example 23 (comprising inventive compound 1015) and Comparative Example 3 (comprising Comparative Compound 4) is truly unexpected. While Applicant asserts the improvement of driving voltage, luminance, efficiency, and life are due to a bicycloheptanyl group in the location of C2, as discussed below and in the previous rejection, Ma teaches norbornyl (bicycloheptanyl) in a compound represented by formula I provides a compound with good stability and heat resistance and provides an organic electroluminescent device with improved luminous efficiency, lifetime, and operating voltage (¶ [0016]). Accordingly, it is already known in the art to expect some degree of improved luminous efficiency, lifetime, and operating voltage when a bicycloheptanyl group is used in a triarylamine compound. Thus, while there is improvement in properties between the instant devices and devices of the comparative examples, it is unclear whether these performances are truly unexpected.
Applicant's argument –On page 156, Applicant request the obviousness-type double patenting rejection be withdrawn in view of the amendments to the claims.
Examiner's response –As shown in the double patenting rejection below, US 12,497,348 B2 recites Compound 21 in claim 8, which reads on the claimed Formula 1 wherein C1 is an unsubstituted cyclohexyl group, C2 is an unsubstituted bicycloheptanyl group, and M is represented by Formula 1-b. Accordingly, the amendments to the claims do not overcome the double patenting rejection.
Claim Objections
Claims 12 and 22 are objected to because of the following informalities: claims 12 and 22 contain blurry compounds. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-28 are 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.
Claims 1 and 22 recite “in a case where M in Formula 1 is represented by Formula 1-b or Formula 1-c, at least one selected from among C1 and C2 in Formula 1 is a bicycloheptanyl group” (first limitation) and also recites “wherein in a case where at least one of C1 and C2 is a substituted or unsubstituted bicycloheptanyl group, M in formula 1 is represented by Formula 1-a or Formula 1-b” (second limitation).
In a case wherein M in Formula 1 is represented by Formula 1-c, it is unclear how both the first limitation and the second limitation may be simultaneously satisfied. For example, when M is represented by Formula 1-c and at least one selected from among C1 and C2 is a bicycloheptanyl group, it is unclear how the second limitation may be satisfied as it requires M to be represented by Formula 1-a or 1-b when at least one of C1 and C2 is a bicycloheptanyl group. For purposes of examination, the first limitation will be interpreted as when M in Formula 1 is represented by Formula 1-b (thus excluding Formula 1-c), at least one selected from among C1 and C2 in Formula 1 is a bicycloheptanyl group.
In light of the interpretation above, claims 12 and 28 recite compounds which read on the claimed Formula 1 wherein at least one of C1 and C2 is a bicycloheptanyl group and M is represented by 1-c. For example, see at least compound 1044. Compound 1044 reads on the claimed Formula 1 wherein both of C1 and C2 is a bicycloheptanyl group and M is represented by Formula 1-c. However, claims 1 and 22 (of which claims 12 and 28 depend upon) recites the newly added amendment that requires wherein in a case where at least one of C1 and C2 is a substituted or unsubstituted bicyclohetanyl group, M in Formula 1 is represented by Formula 1-a or 1-b. Claims 1 and 22 also recite in a case where M in Formula 1 is represented by Formula 1-b or Formula 1-c, at least one selected from among C1 and C2 in Formula 1 is a bicycloheptanyl group. Since at least compound 1044 does not satisfy the amendment, it is unclear how at least compound 1044 reads on the amended claim. For purposes of examination, at least compound 1044 will be interpreted as not present.
Claims 2-21 and 23-28 are further rejected due to their dependency upon indefinite claims 1 and 22.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 12 and 28 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.
As discussed above with respect to the 112(b) rejection of claims 12 and 28, at least compound 1044 does not properly depend from the formula recited in claims 1 and 22. If at least compound 1044 is selected, it does not satisfy all the requirements of Formula 1. Thus claims 12 and 28 do not properly depend from claims 1 and 22.
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 Rejections - 35 USC § 102
(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 22, 25, and 27 are rejected under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Fuchiwaki (US 2018/0019416 A1).
Regarding claims 22, 25, and 27, Fuchiwaki teaches amine derivatives represented by General Formula (1) wherein examples thereof include compound 64 (abstract; ¶ [0073]-[0074]; structure on pg. 20).
64:
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1:
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Compound 64 reads on the claimed Formula 1 wherein:
Ar1 and Ar2 are each an unsubstituted arylene group of 6 ring-forming carbon atoms;
La is an unsubstituted arylene group of 6 ring-forming carbon atoms;
C1 and C2 are each an unsubstituted triphenylsilyl group;
M is represented by Formula 1-c;
Z is NR4;
R3 is an unsubstituted aryl group of 6 ring-forming carbon atoms; and
n3 is an integer of 1.
Additionally, compound 64 reads on the claimed Formulas 5-1 and 9-3 (claims 25 and 27).
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 1-3, 7-9, 11, 13, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Fuchiwaki (US 2018/0019416 A1).
Regarding claims 1-3, 7-9, and 11, Fuchiwaki teaches an organic electroluminescent device having long life by including an amine derivative represented by General Formula (1), wherein examples thereof include compound 64 (abstract; ¶ [0073]-[0074]; structure on pg. 20).
While Fuchiwaki fails to teach a specific example of a device including compound 64, Fuchiwaki teaches a device including an anode, a hole injection layer, a hole transport layer including an amine derivative represented by General Formula (1), an emission layer, an electron transport layer, an electron injection layer, and a cathode (¶ [0110]-[0112]).
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 use compound 64 in the hole transport layer of a device having the structure above, because this would have been combining the prior art elements of Fuchiwaki according to known methods to yield predictable results of an organic electroluminescent device with long life, as taught by Fuchiwaki. See MPEP 2143.I.(A).
Regarding claims 13 and 18, Fuchiwaki teaches the device including a hole injection layer, a hole transport layer including compound 64, and an emission layer, as described above with respect to claim 1.
Fuchiwaki fails to teach the hole injection layer comprises compound 64. However, Fuchiwaki does teach the amine derivative represented by General Formula (1) may be used in a hole injection layer.
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 additionally use compound 64 in the hole injection layer, because this would have been combining the prior art elements of Fuchiwaki according to known methods to yield predictable results of an organic electroluminescent device with long life, as taught by Fuchiwaki. See MPEP 2143.I.(A).
Per claim 13, holes are transported from the anode through the hole injection layer and injected into the hole transport layer and thus the hole injection layer may be considered a hole transport layer. Accordingly, the hole injection layer reads on the claimed first hole transport layer and the hole transport layer reads on the claimed second hole transport layer.
Per claim 18, holes are transported from the anode through the hole injection layer and injected into the hole transport layer and thus the hole injection layer may be considered a hole transport layer. Accordingly, the hole injection layer reads on the claimed hole transport layer and the hole transport layer reads on the claimed hole transport auxiliary layer.
Claims 4, 6, and 23 are rejected under 35 U.S.C. 103 as being unpatentable over Fuchiwaki (US 2018/0019416 A1) as applied to claims 1 and 22 above, and further in view of Ma ‘273 (US 2023/0272273 A1).
Regarding claims 4, 6, and 23, Fuchiwaki teaches the organic electroluminescent device including a hole transport layer comprising the compound 64, as described above with respect to claims 1 and 22.
64:
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Formula (I):
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Compound 64 fails to read on one of the claimed Formulas 3-1 or 3-2, and fails to read on one of the claimed Formulas 4-1 to Formula 4-15. However, Ar1 to Ar3 may be a substituted or unsubstituted aryl or heteroaryl group, wherein examples thereof include fluorene as exemplified in compound 1 (¶ [0006]; see structure on pg. 5).
Ma ‘273 teaches a nitrogen-containing compound having the structure of Chemical formula 1 wherein the phenyl substituent improves film-forming characteristics of the material, and thus the performance of the electronic device including the nitrogen-containing compound has improved performance (abstract; ¶ [0006] and [0012]-[0013]). Examples of compounds having the structure of Chemical formula 1 include compound 1 (see structure on pg. 12).
Chemical formula 1:
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1:
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Therefore, in the modified compound 2, 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
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with
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as shown in compound 1 of Ma ‘273, to arrive at a compound represented by Chemical formula 1 of Ma ‘273, based on the teaching of Ma ‘273. The motivation for doing so would have been to provide a compound with improved film-forming characteristics, and provide a device with improved performance, as taught by Ma ‘273.
The modified compound 64 reads on Chemical formula 1 of Ma ‘273 wherein L, L1 and L2 are each a single bond; Ar1 and Ar2 are each a substituted aryl having 6 carbon atoms; and the substituents of Ar1 and Ar2 are each a triarylsilyl with 18 carbon atoms (see Ma ‘273, ¶ [0025]-[0027]). Accordingly, the modified compound 64 is expected to obtain the benefits of Ma ‘273.
The modified compound 64 reads on the claimed Formula 2-1 wherein Ra1 is hydrogen and m1 is 5, and the claimed Formula 4-1 (claims 4, 6, and 23).
Claims 5 and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Fuchiwaki (US 2018/0019416 A1) as applied to claims 1 and 22 above, and further in view of Wang (English translation of CN 112010759 obtained from Global Dossier).
Regarding claims 5 and 24, Fuchiwaki teaches the organic electroluminescent device including a hole transport layer comprising the compound 64, as described above with respect to claims 1 and 22.
64:
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Formula (I):
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Compound 64 fails to read on one of the claimed Formulas 3-1 or 3-2. However, Fuchiwaki teaches Ar1 to Ar3 may be a substituted or unsubstituted aryl or heteroaryl group, wherein examples thereof include fluorene as exemplified in compound 1 (¶ [0006]; see structure on pg. 5).
Wang teaches a fluorene derivative represented by general formula (1) for use in organic electroluminescent devices, wherein the fluorene derivative obtains high thermal and optical stability, excellent hole transport performance, and high carrier mobility (last paragraph on pg. 1). In general formula (1), each of A, B, and C is an arylamino, a heteroarylamino, an aryl, or a heteroaryl (beginning of pg. 2). Examples of compounds represented by general formula (1) include compound C453 (pg. 16).
general formula (1):
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C453:
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Therefore, in the modified compound 100, 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
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with
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(as shown in Wang’s C453), to arrive at a compound represented by Wang’s general formula (1), based on the teaching of Wang. The motivation for doing so would have been to provide a compound with high thermal and optical stability, excellent hole transport performance, and high carrier mobility, as taught by Wang.
The modified compound 64 reads on Wang’s general formula (1) wherein R and R’ are each a C1 alkyl; R1 and R2 are each hydrogen; A is represented by formula (2), and B and C are each an unsubstituted C6 aryl; and Ar1 and Ar2 are each a substituted C6 aryl; L1 and L2 are each a single bond (see Wang, beginning of pg. 2). Accordingly, the modified compound 64 is expected to obtain the benefits of Wang.
The modified compound 64 reads on the claimed Formula 3-2 wherein Rb3 and Rb4 are each hydrogen and m15 and m16 are each 5 (claims 5 and 24).
Claims 10 and 26 are rejected under 35 U.S.C. 103 as being unpatentable over Fuchiwaki (US 2018/0019416 A1) in view of Ma (US 2022/0306567 A1).
Regarding claims 10 and 26, Fuchiwaki teaches the organic electroluminescent device including a hole transport layer comprising the compound 64, as described above with respect to claims 1 and 22.
64:
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Formula (I):
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Compound 64 fails to read on one of the claimed Formulas 3-1 or 3-2. However, Fuchiwaki teaches Ar1 to Ar3 may be a substituted or unsubstituted aryl or heteroaryl group, wherein examples thereof include fluorene as exemplified in compound 1 (¶ [0006]; see structure on pg. 5).
1:
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Therefore, given the general formula and teachings of Fuchiwaki, 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
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with
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, because Fuchiwaki teaches the Ar1 to Ar3 may suitably be selected as
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. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as the amine derivative in the hole transport layer of the device of Fuchiwaki and possess the benefits taught by Fuchiwaki. See MPEP 2143.I.(B).
The modified compound 64 fails to read on the claimed Formula 1 as it does not comprise a bicycloheptanyl group. However, Fuchiwaki teaches Ar1 to Ar3 may be a substituted aryl group (¶ [0006]).
Ma teaches a nitrogen-containing compound represented by formula I (abstract). Ma teaches the compound represented by formula I introduces norbornyl (bicycloheptanyl) as a substituent, which provides the compound with good stability and heat resistance, and provides an organic electroluminescent device with improved luminous efficiency, lifetime, and operating voltage (¶ [0016]). Ma teaches examples of compounds represented by formula I including compound 2 (pg. 11).
Formula I:
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2:
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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 substitute a triarylsilyl group of the modified compound 64 with a norbornyl group, as shown in Ma’s compound 2, to arrive at a compound represented by Ma’s formula I, based on the teaching of Ma. The motivation for doing so would have been to provide a compound with good stability and heat resistance, and provide a device with improved luminous efficiency, lifetime, and operating voltage, as taught by Ma.
The modified compound 64 reads on Ma’s formula I wherein L is an unsubstituted arylene having 6 carbon atoms; Ar1 is a substituted aryl having 6 carbon atoms and Ar2 is a substituted aryl having 13 carbon atoms; and the substituent of Ar1 is an arylsilyl group and the substituent of Ar2 is alkyl (see Ma, ¶ [0009]-[0013]). Accordingly, the modified compound 64 is expected to obtain the benefits of Ma.
The modified compound 64 reads on the claimed Formula 8-2 (claims 10 and 26).
Claims 12 and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Fuchiwaki (US 2018/0019416 A1) in view of Ma ‘273 (US 2023/0272273 A1) as applied to claims 4 and 23 above, and further in view of Jeong (US 2019/001666 A1).
Regarding claims 12 and 28, Fuchiwaki in view of Ma ‘273 teach the organic electroluminescent device including a hole transport layer comprising the modified compound 64, as described above with respect to claims 4 and 23.
modified 64:
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Formula (I):
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The modified compound 64 fails to read on a claimed compound as it does not comprise adamantyl. However, Fuchiwaki teaches Ar1 to Ar3 may be a substituted or unsubstituted aryl group (¶ [0006]; see structure on pg. 5).
Jeong teaches a compound represented by Formula 4 for use as a hole transporting layer material in an OLED, wherein the compound provides a device with low driving voltage, excellent external quantum efficiency, and excellent thermal stability (¶ [0013]-[0015] and [0057]). In Formula 4, A is an adamantyl group (¶ [0018]). Examples of compounds represented by Formula 4 include the compound below on page 9.
Formula 4:
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Jeong’s compound:
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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 substitute a silyl group
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of the modified compound 64 with
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(as shown in the compound of Jeong above) to arrive at a compound represented by Jeong’s Formula 4, based on the teaching of Jeong. The motivation for doing so would have been to provide a device with low driving voltage, excellent external quantum efficiency, and excellent thermal stability, as taught by Jeong.
The modified compound 64 reads on Jeong’s Formula 4 wherein: X is C(R1)(R2); Ar1 is an unsubstituted aryl group having 6 carbon atoms; R1 and R2 are each an unsubstituted alkyl group having 1 carbon atom; Ar2 is a substituted aryl group having 6 carbon atoms; and A is an adamantyl group (¶ [0018]-[0023]). Accordingly, the modified compound 64 is expected to obtain the benefits taught by Jeong.
The modified compound 64 reads on the claimed compound 885 (claims 12 and 28).
Claims 14 and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Fuchiwaki (US 2018/0019416 A1) as applied to claims 13 and 18 above, and further in view of Hwang (US 2008/0286606 A1).
Regarding claims 14 and 19, Fuchiwaki teaches a device including a hole injection layer including compound 64 (HIL1), a hole transport layer including compound 64, and an emission layer, as described above with respect to claim 1.
Fuchiwaki fails to teach a third layer in the hole transport region.
Hwang teaches an organic light emitting diode including a first hole injection layer and a second hole injection layer, wherein at least one of the first hole injection layer and the second hole injection layer comprises a compound represented by Formula 1, and the first and second hole injection layers are provided between an emissive layer and a hole transport layer (abstract; Fig. 1). Such a device obtains electrical stability, high charge transporting ability, and long life-time (¶ [0008] and [0012]).
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 device of Fuchiwaki an additional hole injection layer (HIL2), wherein HIL2 is provided between the anode and HIL1 or alternatively between HIL1 and HTL, wherein at least one of the two hole-injection layers (HIL1 and HIL2) includes a compound represented by Hwang’s Formula 1, based on the teaching of Hwang. The motivation for doing so would have been to provide a device with electrical stability, high charge transporting ability, and long life-time, as taught by Hwang.
The resulting device includes either of the following structures in the hole transport region: HIL2/HIL1/HTL or HIL1/HIL2/HTL.
Per claim 14, holes are transported from the anode through the hole-injection layer, and injected into the hole transport layer. Accordingly, a hole injection layer may be considered a hole transport layer. Thus, in the device structure comprising HIL1/HIL2/HTL. HIL1 reads on the claimed first hole transport layer, HIL2 reads on the second hole transport layer, and HTL reads on the claimed third hole transport layer. As discussed above, both HIL1 and HTL include compound 64.
Per claim 19, holes are transported from the anode through the hole-injection layer, and injected into the hole transport layer. Accordingly, a hole injection layer may be considered a hole transport layer. Thus, in the device structure comprising HIL2/HIL1/HTL, HIL2 reads on the claimed hole transport layer, HIL1 reads on the claimed first hole transport auxiliary layer, HTL reads on the claimed second hole transport auxiliary layer. As discussed above, HIL1 includes compound 64.
Claims 15-17 are rejected under 35 U.S.C. 103 as being unpatentable over Fuchiwaki (US 2018/0019416 A1) as applied to claim 13 above, and further in view of Lee (US 2014/0117329 A1).
Regarding claims 15-17, Fuchiwaki teaches the device including a hole injection layer (first hole transport layer) and a hole transport layer (second hole transport layer), wherein the hole injection layer and the hole transport layer each comprise compound 64, as described above with respect to claim 13.
Fuchiwaki fails to teach the hole transport layer includes an amine derivative represented by the claimed Formula 10.
Lee teaches an amine-based compound represented by Formula 1 for use in an organic light-emitting device, wherein examples thereof include Compound 1 (abstract; ¶ [0010]; pg. 27). The amine-based compound provides the device with low driving voltage, high efficiency, high luminance, and long lifetime (¶ [0047]). Lee teaches an example of such a device in Example 1 wherein Compound 1 is used to form the hole transport layer (¶ [0324]).
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 provide Compound 1 in the hole transport layer in the device of Fuchiwaki, based on the teaching of Lee. The motivation for doing so would have been to provide a device with low driving voltage, high efficiency, high luminance, and long lifetime, as taught by Lee.
Compound 1 is identical to the claimed compound A27 (claim 17) and is reproduced below in comparison to the claimed Formula 10 (claim 15).
1:
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10:
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Compound 1 reads on the claimed Formula 10 wherein:
L1 is a direct linkage;
R11, R13, and R14 are each an unsubstituted aryl group of 6 ring-forming carbon atoms, and R12 is an unsubstituted aryl group of 12 ring-forming carbon atoms;
R15 to R18 are each a hydrogen atom; and
n11 and n14 are each 4 and n12 and n13 are each 3.
Additionally, Compound 1 reads on the claimed Formula 11-2 (claim 16).
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Fuchiwaki (US 2018/0019416 A1) in view of Hwang (US 2008/0286606 A1) as applied to claim 19 above, and further in view of Lee ‘919 (US 2017/0330919 A1).
Regarding claim 20, Fuchiwaki in view of Hwang teach the light-emitting device including the additional hole injection layer HIL2 (hole transport layer), the hole injection layer HIL1 (first hole transport auxiliary layer), and the hole transport layer (second hole transport auxiliary layer), as described above with respect to claim 19.
Fuchiwaki in view of Hwang are silent as to the refractive index of the hole injection layer and the hole transport layer.
Lee ‘919 teaches an organic light emitting diode comprising a hole transport layer, wherein the hole transport layer may include a hole-transporting layer and a hole-injection layer, wherein the hole transport layer may have a refractive index in a range of 1.0 to 1.6 in the blue wavelength region (e.g., about 450 nm) (abstract; ¶ [0058] and [0081]). By using a hole transport layer with a relatively low refractive index, the light-emitting efficiency is improved (¶ [0107]).
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 modify the hole injection layer and hole transport layer of the device of Fuchiwaki in view of Hwang such that the layers have a refractive index in a range of 1.0 to 1.6 in the blue wavelength region, based on the teaching of Lee ‘919. The motivation for doing so would have been to improve light-emitting efficiency, as taught by Lee ‘929.
A prima facie case of obviousness exists where the claimed ranges overlap or lie inside ranges disclosed by the prior art. See MPEP 2144.05.
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over Fuchiwaki (US 2018/0019416 A1) in view of Hwang (US 2008/0286606 A1) as applied to claim 19 above, and further in view of Shitagaki (US 2009/0102368 A1).
Regarding claim 21, Fuchiwaki in view of Hwang teach the device including the additional hole injection layer HIL2 (hole transport layer), the hole injection layer HIL1 (first hole transport auxiliary layer), and the hole transport layer (second hole transport auxiliary layer), as described above with respect to claim 19.
Fuchiwaki in view of Hwang are silent as to the HOMO energy level of the hole transport layer being greater than the HOMO energy level of the hole injection layer.
Shitagaki teaches a light-emitting element including a hole-injecting layer and a hole-transporting layer wherein the absolute value of the HOMO level of the hole-transporting layer is larger than that of the hole-injecting layer, as this increases the luminous efficiency of the light-emitting element (abstract).
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 modify the hole injection layer and hole transport layer of the device of Watabe in view of Ma and Hwang such that the absolute value of the HOMO level of the hole-transport layer is larger than that of the hole-injection layer, based on the teaching of Shitagaki. The motivation for doing so would have been to provide a device with increased luminous efficiency, as taught by Shitagaki.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-3, 6-13, 15-18, 22, and 25-28 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. 12,497,348 B2. Although the claims at issue are not identical, they are not patentably distinct from each other because claim 8 of ‘348 recites compounds for use in a light-emitting element which meet the limitations of claims 1, 3, 6-12, 22, and 25-28 of ‘819.
For example, claims 8 and 20 recite compounds 21 and 24, which read on the limitations of the amine compound of claims 1, 3, 6-12, 22, and 25-28 of ‘819.
Compound 21 of ‘348:
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Formula 1 of ‘819: 1:
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Compound 21 of ‘348 reads on the claimed Formulas 1 and 8-2 of ‘819 (claims 1, 10, and 22) wherein:
Ar1 and Ar2 are each an unsubstituted arylene group of 6 ring-forming carbon atoms;
La is a direct linkage;
C1 is an unsubstituted cyclohexyl group (Formula 7-1) and C2 is an unsubstituted bicycloheptanyl group (Formula 7-2) (claim 9);
M is represented by Formula 1-b; and
Rc and Rd are each an unsubstituted alkyl group of 1 carbon atom, Re and Rg to Rl are each hydrogen, and Rf is a part connected with Formula 1.
Additionally, Compound 21 of ‘348 reads on the claimed Formulas 5-1, 6-1, and 8-2, and the claimed compound 1015 (claims 7-8, 12, 25-26, and 28).
Compound 24 of ‘348:
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Similarly, Compound 24 of ‘348 reads on the claimed Formulas 1 and 8-2 (claims 1 and 22) wherein:
Ar1 and Ar2 are each an unsubstituted arylene group of 6 ring-forming carbon atoms;
La is a direct linkage;
C1 is an unsubstituted cyclohexyl group (Formula 7-1) and C2 is an unsubstituted bicycloheptanyl group (Formula 7-2) (claim 9);
M is represented by Formula 1-c;
Z is O; and
R3 is hydrogen and n3 is an integer of 7.
Additionally, compound 24 of ‘348 reads on the claimed Formula 9-1 (claims 11 and 27), and the claimed compound 1018 (claims 12 and 28).
Additionally, ‘348 recites Formula 1 in claims 1, 6, 14, and 17, Formulas 1-1 and 1-2 in claims 4 and 15, Formula 1-2A in claims 5 and 16, Formula 1A in claims 7 and 18, and Formula 1A-1 in claim 19. As evidenced by the compounds in claims 12 and 20, 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 variables of Formula 1, Formulas 1-1 and 1-2, Formula 1-2A, Formula 1A, and Formula 1A-1 to arrive at the instant claimed Formula 1 comprising the limitations of claims 1, 3, 6-11, 22, and 25-27 of ‘819, because it would have been choosing from a list of variables specifically taught, which would have been a choice from a finite number of identified, predictable solutions of a compound possessing the benefits taught by ‘348. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 1, Formulas 1-1 and 1-2, Formula 1-2A, Formula 1A, and Formula 1A-1 having the properties taught by ‘348 in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Additionally, claims 1-2 and 9-13 of ‘014 correspond to claims 1-2, 13, and 15-17 of ‘819, as shown below.
US 12,497,348 B2
17/809,819
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353
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141
425
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102
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297
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375
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50
370
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462
341
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52
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496
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Wherein the compounds in Compound Group 2 of ‘819 are identical to the compounds in Group 2-1 and 2-2 of ‘348
Additionally, claim 3 of ‘348 recites the hole transport region comprises a hole injection layer on the first electrode, and a hole transport layer on the hole injection layer, and the hole transport layer comprises the amine compound. As holes are transported through a hole injection layer (see ¶ [0004] of ‘348), the hole injection layer may be considered a hole transport layer or a hole transport auxiliary layer. Accordingly, claim 3 of ‘348 corresponds to claim 18 of ‘819.
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/Primary Examiner, Art Unit 1786
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