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, 5, and 22 are amended due to Applicant's amendment dated 11/04/2025. Claims 1-28 are pending.
Response to Amendment
The objection to the drawings as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 11/04/2025.
The rejection of claim 5 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 11/04/2025. The rejection is withdrawn.
The rejection of claims 1-3, 9, 11, 22, and 27 under 35 U.S.C. 102(a)(1) as being anticipated by Dong (English translation of CN 110845394 A obtained from Global Dossier) is overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is withdrawn.
The rejection of claims 7-8, 12, 25, and 28 under 35 U.S.C. 103 as being unpatentable over Dong is overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is withdrawn.
The rejection of claims 13-14 and 18-19 under 35 U.S.C. 103 as being unpatentable over Dong in view of Kim (US 2015/0311451 A1) is overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is withdrawn.
The rejection of claims 15-17 under 35 U.S.C. 103 as being unpatentable over Dong in view of Kim and Lee (US 2014/0117329 A1) is overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is withdrawn.
The rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Dong in view of Kim and Lee ‘919 (US 2017/0330919 A1) is overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is withdrawn.
The rejection of claim 21 under 35 U.S.C. 103 as being unpatentable over Dong in view of Kim and Zhang (US 2021/0351370 A1) is overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is withdrawn.
The rejection of claims 1-3, 7-10, 12-13, 18, 22, 2-26, 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 not overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is maintained.
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 not overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is maintained.
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 not overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is maintained.
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 not overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is maintained.
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 not overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is maintained.
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 not overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is maintained.
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 not overcome due to the Applicant’s amendment dated 11/04/2025. The rejection is maintained.
The provisional 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 co-pending application No. 17/588,041 is herein revised to a non-provisional rejection due to the issue of Patent US 12,497,348 B2 (granted application No. 17/588,041).
Response to Arguments
Applicant’s arguments on pages 156-162 of the reply dated 11/04/2025 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 156-158, Applicant argues the cited reference Dong fails to read on the claims as amended which exclude wherein C1 and C2 are both a substituted or unsubstituted bicycloheptanyl groups.
Examiner's response –As discussed in greater detail in the rejection below, while Dong alone fails to teach the claims as amended, the newly cited reference Jeong (US 2019/0016666 A1) provides motivation to modify a compound of Dong to arrive at a compound of the claimed Formula 1. Accordingly, the cited references teach the claims as amended.
Applicant's argument –On pages 158-161, Applicant argues compounds of the instant application show unexpected results over the compound of Watabe. Applicant points to Table 2 on instant pages 220-221 for support to show that the inventive compounds achieve unexpected results over Comparative Compound C6 of Comparative Example 13, which Applicant alleges is identical to Watabe’s compound 100.
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 Watabe.
For example, as shown below and on instant page 201 and Watabe page 14, Comparative Compound C6 is not identical to Watabe’s compound 100. Comparative Compound C6 comprises an amine group on position 3 of the fluorene group and in contrast, Watabe’s compound 100 comprises an amine group on position 2 of the fluorene group. Where the comparison is not identical with the reference disclosure, deviations therefrom should be explained, and if not explained should be noted and evaluated, and if significant, explanation should be required. MPEP 716.02(e). Accordingly, a comparison to the closest prior art has not been made.
C6:
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210
243
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100:
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239
272
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However, even if Comparative Compound C6 was identical to Watabe’s compound 100, a comparison to the closest prior art has still not been made. As shown by the structures below, the closest inventive compound to Watabe’s compound 100 is inventive compound 995.
100:
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239
272
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995:
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347
339
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As shown by the structure above, Watabe’s compound 100 comprises a cyclohexane group in the location of the claimed C1 and compound 995 comprises an adamantyl group in the location of the claimed C1. As no explanation is provided for compounds having these different groups it is unclear if a comparison between compounds comprising the same structure of Watabe’s compound 100 (i.e., a cyclohexane group in the location of the claimed C1) that also comprises a bicycloheptanyl group in the location of the claimed C2 would obtain the same results discussed by Applicant. Accordingly, a comparison of the closest prior art has not been made.
Additionally, it should also be noted that even if even if Comparative Compound C6 was identical to Watabe’s compound 100, a comparison to the closest prior art has not been made with respect to the device of Comparative Example 13 (which comprises Comparative Compound C6). As shown in Table 2 on instant page 221, Comparative Example 13 comprises a first hole transport layer of Comparative Compound C6, a second hole transport layer of Compound A13, and a third hole transport layer of Comparative Compound C5. In contrast, inventive Example 33 comprises a first hole transport layer of Compound 995, a second hole transport layer of Compound A13, and a third hole transport layer of Compound 995. As Comparative Example 13 and Example 33 comprise different third hole transport layers, it is unclear how much the degree of device improvement may be attributed to the use of inventive Compound 995 over Comparative Compound C6. Accordingly, Applicant has not made a comparison to the closest prior art.
As the comparative and inventive devices of Applicant comprise different structure and materials, and as the devices of Applicant comprise different compounds than the compounds of Watabe, a comparison is not being made to the closest prior art. Where the comparison is not identical with the reference disclosure, deviations therefrom should be explained, and if not explained should be noted and evaluated, and if significant, explanation should be required. MPEP 716.02(e).
Commensurate in Scope
As discussed below and in the previous rejection, Watabe’s compound includes a cyclohexane group in the location of the claimed C1, and includes an amine group in the second position of the fluorene ring. These are within the scope of the claims. As there are no results comprising the structures and materials of the prior art, it is unclear if the same results discussed by Applicant would be present.
Applicant's argument –On page 162, Applicant argues a person with ordinary skill in the art would not have made the modification proposed in the rejection (i.e., substituting a cyclohexyl group with a bicycloheptanyl group) because it would have increased the number of condensed rings, which is taught away from Watabe in ¶ [0242].
Examiner's response – This does not constitute a teaching away because the prior art references do not criticize, discredit, or otherwise discourage substituting a cyclohexyl group with a bicycloheptanyl group and the prior art references do not expressly exclude their combination.
¶ [0242] teaches the refractive index tends to increase with an increase in the number of condensed rings. Watabe teaches the third aromatic group is a condensed ring, and is preferably a fluorene ring (¶ [0242]). Thus, in the context of Watabe’s general formula G1, the third aromatic group is the fluorene ring, and the discussion of reducing the number of condensed rings in ¶ [0242] corresponds to the fluorine ring (¶ [0245]).
G1:
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114
187
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As discussed below and in the previous rejection, compound 100 of Watabe is modified by replacing a cyclohexyl group in position Ar1 or Ar2 with a bicycloheptanyl group. Watabe teaches Ar1 and Ar2 are each a substituent with a benzene ring or a substituent in which two or three benzene rings are bonded to each other (¶ [0246]). Thus, there is nothing in Watabe that relates Ar1 or Ar2 with the third aromatic group or a condensed ring, and thus ¶ [0242] does not limit the structures that Ar1 or Ar2 may be selected as.
Accordingly, there is nothing in ¶ [0242] that teaches away from substituting a cyclohexyl group with a bicycloheptanyl group.
Applicant's argument –On page 162, 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 (granted application No. 17/588,041) recites Compound 21 in claim 8, which reads on the claimed Formula 1 wherein C1 is an unsubstituted cyclohexyl group and C2 is an unsubstituted bicycloheptanyl group. Accordingly, the amendments to the claims do not overcome the double patenting rejection.
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 12 and 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 12 and 28 recite compounds which read on the claimed Formula wherein C1 and C2 are each a bicycloheptanyl groups. For example, see at least compounds 1035-1054 and 1063-1066. However, claims 1 and 22 (of which claims 12 and 28 depend upon) recite the newly added amendment that excludes the case wherein both C1 and C2 are bicycloheptanyl groups. Since some of the compounds in claims 12 and 28 do not satisfy the amendment, it is unclear how these compounds read on the amended claim. For purposes of examination, the compounds including bicycloheptanyl groups in the locations of C1 and C2 will be interpreted as not present.
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, the compounds containing bicycloheptanyl groups in the locations of C1 and C2 do not properly depend from the formula recited in claims 1 and 22. If these compounds are selected, they do 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 § 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 11 and 27 are rejected 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 2019/0016666 A1).
Regarding claims 11 and 27, Dong teaches an organic electroluminescent device comprising an aromatic amine compound represented by Formula I, wherein the device obtains good thermal stability, high luminous efficiency, and long life (beginning of pg. 2). Dong teaches examples of such devices including Device 9 including an anode, a hole injection layer, a hole transport layer of compound 315, a light-emitting layer, an electron transport layer, and electron injection layer, and a cathode (beginning of pg. 17 and beginning of pg. 18).
315:
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277
372
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Compound 315 fails to read on the claimed Formula 1 as it comprises two bicycloheptanyl groups. However, Dong teaches Ar may be a substituted C6-C30 aryl (middle of pg. 2).
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 5.
Formula 4:
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84
173
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Jeong’s compound:
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239
321
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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 one of the bicycloheptanyl groups of Compound 315 with an adamantyl group to arrive at a compound represented by Jeong’s Formula 4 (as shown in the compound of Jeong above), 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 315 reads on Jeong’s Formula 4 wherein: X is O; Ar1 is an unsubstituted aryl group having 12 carbon atoms; Ar2 is a substituted aryl group having 12 carbon atoms; and A is an adamantyl group (¶ [0018]-[0023]). Accordingly, the modified Compound 315 is expected to obtain the benefits taught by Jeong.
The modified compound 315 is reproduced below in comparison to the claimed Formula.
modified 315:
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359
676
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1:
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173
256
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The modified Compound 315 reads on the claimed Formulas 1 and 9-1 (claims 11 and 27) wherein:
Ar1 and Ar2 are each an unsubstituted arylene group of 12 ring-forming carbon atoms;
La is a direct linkage;
C1 is an unsubstituted adamantyl group and C2 is an unsubstituted bicycloheptanyl group;
M is represented by Formula 1-c;
Z is O; and
R3 is hydrogen and n3 is an integer of 7.
Claims 1-3, 7-10, 12-13, 18, 22, 25-26, and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Watabe (US 2021/0005814 A1) in view of Ma (US 2022/0306567 A1).
Regarding claims 1-3, 7-10, 12-13, 18, 22, 25-26, and 28, Watabe teaches a light-emitting device including a monoamine compound represented by general formula (G1) as a material for a hole-transport layer (abstract; ¶ [0001] and [0055]). Examples thereof include Device 1-1 which comprises a first electrode, a hole-injection layer comprising compound 100 (also referred to as compound dchPAF), a hole-transport layer formed of compound 100, a light-emitting layer, an electron-transport layer, an electron-injection layer, and a second electrode (¶ [0666]-[0673]; structure on pgs. 14 and 126).
G1:
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164
284
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100:
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236
271
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Compound 100 fails to read on the claimed Formula 1 as it does not comprise a bicycloheptanyl group. However, Watabe teaches one or both of Ar1 and Ar2 have one or more hydrocarbon groups each having 1 to 12 carbon atoms (¶ [0056]).
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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70
136
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2:
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268
282
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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 cyclohexyl group of compound 100 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 100 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 a cycloalkyl group and the substituent of Ar2 is alkyl (see Ma, ¶ [0009]-[0013]). Accordingly, the modified compound 100 of Watabe in view of Ma is expected to obtain the benefits of Ma.
The modified compound 100 has the same structure as the claimed compound 1015 (claims 12 and 28) and is reproduced below in comparison to Formula 1.
modified 100:
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394
394
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1:
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173
256
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The modified compound 100 reads on the claimed Formulas 1 and 8-2 (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, the modified compound 100 reads on the claimed Formulas 5-1, 6-1, and 8-2 (claims 7-8 and 25-26).
Per claim 13, holes are transported from the anode through the hole-injection layer, and injected into the hole-transport layer (¶ [0294]). 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. As discussed above, the hole-injection layer comprises the modified compound 100.
Per claim 18, holes are transported from the anode through the hole-injection layer, and injected into the hole-transport layer (¶ [0294]). Thus, the hole-injection layer may be considered a hole transport layer. Accordingly, as holes are transported in the hole-injection layer, 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 Watabe (US 2021/0005814 A1) in view of Ma (US 2022/0306567 A1) as applied to claim 1 above, and further in view of Ma ‘273 (US 2023/0272273 A1).
Regarding claims 4, 6, and 23, Watabe in view of Ma teach the light-emitting device including a hole-injection layer and a hole-transport layer, wherein the hole-injection layer and the hole-transport layer each comprise the modified compound 100, as described above with respect to claim 1.
Modified 100:
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394
394
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G1:
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111
190
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The modified compound 100 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 as it does not comprise a phenyl substituent on the fluorene group. However, Watabe teaches the monoamine compound includes a first aromatic group, a second aromatic group, and a third aromatic group wherein the third aromatic group includes a fluorene skeleton that may be substituted or unsubstituted (¶ [0020], [0027], and [0030]). Additionally, as shown by the general formula (G1) above, Watabe does not limit the attachment point of the fluorene group to the nitrogen atom (¶ [0055]).
Ma ‘273 teaches a nitrogen-containing compound having the structure of Chemical formula 1 (abstract). The linkage of the arylamino to the position 3 of dimethylfluorenyl provides a deep HOMO energy level and a high hole mobility, 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 (¶ [0006] and [0012]-[0013]).
Chemical formula 1:
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154
215
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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 attach the arylamino group in the 3 position of the dimethylfluorenyl group and to further substitute the dimethylfluorenyl group with a phenyl substituent in the 5 position, 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 deep HOMO energy level, high hole mobility, and improved film-forming characteristics, and provide a device with improved performance, as taught by Ma ‘273.
The modified compound 100 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 cycloalkyl with 6 or 7 carbon atoms (see Ma ‘273, ¶ [0025-[0027]). Accordingly, the modified compound 100 of Watabe in view of Ma and Ma ‘273 is expected to obtain the benefits of Ma ‘273.
The modified compound 100 of Watabe in view of Ma and Ma ‘273 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, 12, 24, and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Watabe (US 2021/0005814 A1) in view of Ma (US 2022/0306567 A1) as applied to claim 1 above, and further in view of Wang (English translation of CN 112010759 obtained from Global Dossier).
Regarding claims 5, 12, 24, and 28, Watabe in view of Ma teach the light-emitting device including a hole-injection layer and a hole-transport layer, wherein the hole-injection layer and the hole-transport layer each comprise the modified compound 100, as described above with respect to claim 1.
modified 100:
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394
394
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The modified compound 100 fails to read on one of the claimed Formulas 3-1 or 3-2 as it does not comprise two phenyl substituents on the fluorene group. However, Watabe teaches the monoamine compound includes a first aromatic group, a second aromatic group, and a third aromatic group wherein the third aromatic group includes a fluorene skeleton that may be substituted or unsubstituted (¶ [0020], [0027], and [0030]).
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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192
280
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C453:
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147
229
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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 phenyl groups in the 3- and 7-positions of the fluorene group (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 100 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; Ar1 and Ar2 are each a substituted C6 aryl; L1 and L2 are each a single bond; and the substituents of Ar1 and Ar2 are each a C6 or C7 cycloalkyl (see Wang, beginning of pg. 2). Accordingly, the modified compound 100 of Watabe in view of Ma and Wang is expected to obtain the benefits of Wang.
The modified compound 100 of Watabe in view of Ma and Wang reads on the claimed compound 703 (claims 12 and 28), and additionally 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 14 and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Watabe (US 2021/0005814 A1) in view of Ma (US 2022/0306567 A1) as applied to claims 13 and 18 above, and further in view of Hwang (US 2008/0286606 A1).
Regarding claims 14 and 19, Watabe in view of Ma teaches the light-emitting device including a hole-injection layer (HIL1) and a hole-transport layer (HTL), wherein HIL1 and HTL each comprise the modified compound 100, as described above with respect to claims 13 and 18.
Watabe in view of Ma fail 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 Watabe in view of Ma 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 (¶ [0294]). 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 the modified compound 100.
Per claim 19, holes are transported from the anode through the hole-injection layer, and injected into the hole-transport layer (¶ [0294]). 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 the modified compound 100.
Claims 15-17 are rejected under 35 U.S.C. 103 as being unpatentable over Watabe (US 2021/0005814 A1) in view of Ma (US 2022/0306567 A1) as applied to claim 13 above, and further in view of Lee (US 2014/0117329 A1).
Regarding claims 15-17, Watabe in view of Ma teaches the light-emitting device including a hole-injection layer (first hole transport layer) and a hole-transport layer (second hole transport layer), wherein the hole-injection layer comprises the modified compound 100, as described above with respect to claim 13.
Watabe in view of Ma fail 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 Watabe in view of Ma, 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 Watabe (US 2021/0005814 A1) in view of Ma (US 2022/0306567 A1) and 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, Watabe in view of Ma and 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.
While Watabe teaches a layer with a low refractive index leads to higher external quantum efficiency (¶ [0295]-[0296]), Watabe in view of Ma and 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 Watabe in view of Ma and 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 higher external quantum efficiency, as taught by Watabe, and 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 Watabe (US 2021/0005814 A1) in view of Ma (US 2022/0306567 A1) and Hwang (US 2008/0286606 A1) as applied to claim 19 above, and further in view of Shitagaki (US 2009/0102368 A1).
Regarding claim 21, Watabe in view of Ma and 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.
Watabe in view of Ma and 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.
In the previous rejection, claims 1-3, 6-13, 15-18, 22, and 25-28 were provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of copending Application No. 17/588,041. However, due to the issue of Patent US 12,497,348 B2 (granted application No. 17/588,041), claims 1-3, 6-13, 15-18, 22, and 25-28 are now rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. US 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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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. According, claim 3 of ‘348 corresponds to claim 18 of ‘819.
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