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 .
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Election/Restrictions
Applicant’s election without traverse of Group (I)(A)(i) in the reply filed on 04/12/2024 was previously acknowledged.
Group (I)(A)(i) corresponds to a compound represented by Formula 10, a11 and a12 are both 0, and none of Ar1 to Ar4 includes an amine group.
Claims 1-11 and 13-20 encompass the elected species.
Response to Amendment
The amendment of 06/05/2026 is entered.
Claims 1, 9, 13, and 20 are amended due to the applicant's amendment.
Claims 1-11 and 13-20 are pending.
The rejections under 35 U.S.C. 103 as set forth in the previous Office action are each overcome due to the applicant's amendment. The rejections are withdrawn.
However, as outlined below, new grounds of rejection have been made in view of Kang et al. KR-20140142923-A.
Response to Arguments
Insofar as the arguments apply to the new grounds of rejection outlined below, the applicants' arguments on pages 28-31 of the reply dated 06/05/2026 with respect to the rejections of record have been fully considered, but they are not persuasive.
Applicant's argument – The applicant argues on page 30 that the rejections set forth in the previous Office action are overcome due to the applicant's amendment.
Examiner's response – The claims did not previously require the amended limitations of the narrower definition of Ar1 to Ar4 that no longer includes "a phenanthrenyl group" and "a triphenylenyl group" and the amended limitations are met in the new grounds of rejection below in view of the teachings of Kang et al. KR-20140142923-A.
Applicant's argument – The applicant argues bridging pages 30-31 that because claims 2-8, 10, 11 and 13-20 depend from claim 1 or 9, they each incorporate all of the terms and features of their base claim, in addition to other features, which together further patentably distinguish these claims over the art of record when considered as a whole.
Examiner's response – The applicant has not provided additional arguments with respect to the rejections of these dependent claims and therefore, for the reasons outlined above, this is not found persuasive.
Claim Objections
Claim 20 is objected to because of the following informalities: the chemical structure formulae of the compounds in claim 20 is of poor resolution. 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.
Claim 20 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claim 20, the compounds recited in the claim all appear be compounds of the claimed Formula 1 wherein two (or more) of Ar1 to Ar4 are a phenyl group. See for example compounds 2 and 173:
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. However, claim 9, from which claim 20 depends, recites "two of Ar1 to Ar4 being a phenyl group is excluded." Therefore, it is unclear how the compounds recited in claim 20 may meet the recited Formula 1 in the parent claim and claim 20 is indefinite.
For purposes of examination, the claim will be interpreted such that it is an independent claim and the scope of the claim includes all of the listed compounds.
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.
Claim 20 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Regarding claim 20, the compounds recited in the claim all appear be compounds of the claimed Formula 1 wherein two (or more) of Ar1 to Ar4 are a phenyl group. See for example compounds 2 and 173:
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. However, claim 9, from which claim 20 depends, recites "two of Ar1 to Ar4 being a phenyl group is excluded." Therefore, claim 20 fails to further limit the subject matter of the claim upon which it depends and/or for fails to include all the limitations of the claim upon which it depends.
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 following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-4, 7-11, and 13-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kang et al. KR-20140142923-A (hereinafter "Kang-KR" and see English language machine translation referred to herein as "Kang-MT") in view of Li et al. US-20020076576-A1 (hereinafter "Li").
Regarding claims 1-4 and 7-8, Kang teaches an organic electroluminescent device comprising a first electrodes formed on a substrate, an organic material layer between a first electrode and a second electrode, and a light efficiency improvement layer on the first and/or second electrode (Kang-KR, page 6 of 23, lines 3-5), wherein the light-efficiency-improvement layer comprises a compound represented by a formula (1) (Kang-MT, page 7 of 23, lines 31-33), and wherein the first electrode is an anode and the second electrode is a cathode (Kang-KR, page 9 of 23, lines 24-29). Kang teaches the organic material layer comprising a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer (Kang-MT, page 6 of 23, lines 18-20), wherein the compound is additionally contained in the hole transport layer (Kang-MT, page 6 of 23, lines 26-28). Kang teaches a host / dopant system may be used as a light emitting material (page 1 of 23, lines 37) and teaches examples wherein the dopant is a phosphorescent dopant (Kang-KR, page 16 of 23, lines 21-22), and wherein the electron transport region comprises an alkali metal (Kang-KR, page 16 of 23, lines26-27). Kang teaches specific examples of the compound represented by formula (1) of Kang including compounds P-27 and P-28
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(Kang-KR, page 17).
Kang does not exemplify a compound that meets the claimed Formula 1. For example, the compounds of Kang do not show wherein at least one of the central phenylene groups is fully deuterated (substituted with four deuteriums). However, Kang teaches the groups may be substituted with deuterium (Kang-KR, page 5 of 23, line 17).
Li teaches that a deuterated organic system has better thermal stability, and longer lifetime in optoelectronic devices (¶ [0009]) and deuterated organic semiconductor materials exhibit improved performance including brighter luminescence, better thermal stability, and longer lifetime compared to non-deuterated organic semiconductor materials (Abstract, ¶ [0023], and [0077]).
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 compounds of Kang including compounds P-27 and P-28 in the device of Kang to include at least one deuterium, based on the teachings of Li. The motivation for doing so would have been to obtain brighter luminescence, better thermal stability, and longer lifetime, as taught by Li.
Further, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to have fully deuterated at least one of the central phenylene groups, because each position would have been a choice from two options, H or D, which would have been a choice from a finite number of identified, predictable solutions of a compound useful in the hole transport layer of the device of Kang and possessing the beneficial properties taught by Kang. One of ordinary skill in the art would have been motivated to produce additional compounds represented by the general formula of Kang and being partially or fully deuterated based on the teachings of Li having the benefits as described above taught by Li in order to pursue the known options within their technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified compounds of Kang in view of Li is a compound of the claimed Formula 1.
For example, the modified compounds P-27 and P-28 of Kang in view of Li are each a compound of the claimed Formula 1 wherein:
L1 to L4, L11, and L12 are not required to be present;
a1 to a4, a11, and a12 are each 0;
Ar1 is a phenyl group, A-r2 is a dibenzofuranyl group or a dibenzothiophenyl group, Ar3 is a phenyl group, and Ar4 is a dibenzofuranyl group or a dibenzothiophenyl group each of which is either partially, full, or not deuterated;
R1 to R3 are not required to be present;
b1 to b3 are each 0; and
c1 to c3 are each 0 to 4, wherein at least one of c1 to c3 is 4.
Regarding claims 1-4, 7-11, and 13-19, Kang teaches an organic electroluminescent device comprising a first electrodes formed on a substrate, an organic material layer between a first electrode and a second electrode, and a light efficiency improvement layer on the first and/or second electrode (Kang-KR, page 6 of 23, lines 3-5), wherein the light-efficiency-improvement layer comprises a compound represented by a formula (1) (Kang-MT, page 7 of 23, lines 31-33), and wherein the first electrode is an anode and the second electrode is a cathode (Kang-KR, page 9 of 23, lines 24-29). Kang teaches the organic material layer comprising a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer (Kang-MT, page 6 of 23, lines 18-20), wherein the compound is additionally contained in the hole transport layer (Kang-MT, page 6 of 23, lines 26-28). Kang teaches a host / dopant system may be used as a light emitting material (page 1 of 23, lines 37) and teaches examples wherein the dopant is a phosphorescent dopant (Kang-KR, page 16 of 23, lines 21-22), and wherein the electron transport region comprises an alkali metal (Kang-KR, page 16 of 23, lines 26-27). Kang teaches the device attains improved light emission efficiency and lowered driving voltage (page 1 of 23, lines 9-11). Kang teaches specific examples of the compound represented by formula (1) of Kang including compounds P-27 and P-28
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(Kang-KR, page 17).
Kang does not exemplify a compound that meets the claimed Formula 1. For example, the compounds of Kang do not show (1) one or three, but not two of Ar1 to Ar4 of Kang's general formula as a phenyl group and (2) wherein at least one of the central phenylene groups is fully deuterated (substituted with four deuteriums).
Regarding (1), Kang teaches Ar1 to Ar4 may be a C6 to C60 aryl group, a fluorenyl group, among others (page 8 of 23, line 5).
Therefore, given the general formula and teachings of Kang, 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 phenyl groups for a fluorenyl group, because Kang teaches the variable may suitably be selected as such. 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 in the device of Kang and possess the beneficial properties of improved light emission efficiency and lowered driving voltage, taught by Kang. See MPEP § 2143.I.(B).
Regarding (2), However, Kang teaches the groups may be substituted with deuterium (Kang-KR, page 5 of 23, line 17).
Li teaches that a deuterated organic system has better thermal stability, and longer lifetime in optoelectronic devices (¶ [0009]) and deuterated organic semiconductor materials exhibit improved performance including brighter luminescence, better thermal stability, and longer lifetime compared to non-deuterated organic semiconductor materials (Abstract, ¶ [0023], and [0077]).
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 compounds of Kang including compounds P-27 and P-28 in the device of Kang to include at least one deuterium, based on the teachings of Li. The motivation for doing so would have been to obtain brighter luminescence, better thermal stability, and longer lifetime, as taught by Li.
Further, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to have fully deuterated at least one of the central phenylene groups, because each position would have been a choice from two options, H or D, which would have been a choice from a finite number of identified, predictable solutions of a compound useful in the hole transport layer of the device of Kang and possessing the beneficial properties taught by Kang. One of ordinary skill in the art would have been motivated to produce additional compounds represented by the general formula of Kang and being partially or fully deuterated based on the teachings of Li having the benefits as described above taught by Li in order to pursue the known options within their technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified compounds of Kang in view of Li is a compound of the claimed Formula 1.
For example, the modified compounds P-27 and P-28 of Kang in view of Li are each a compound of the claimed Formula 1 wherein:
L1 to L4, L11, and L12 are not required to be present;
a1 to a4, a11, and a12 are each 0;
Ar1 is a fluorenyl group, A-r2 is a dibenzofuranyl group or a dibenzothiophenyl group, Ar3 is a phenyl group, and Ar4 is a dibenzofuranyl group or a dibenzothiophenyl group each of which is either partially, full, or not deuterated;
R1 to R3 are not required to be present;
b1 to b3 are each 0; and
c1 to c3 are each 0 to 4, wherein at least one of c1 to c3 is 4.
Regarding claim 20, Kang teaches an organic electroluminescent device comprising a first electrodes formed on a substrate, an organic material layer between a first electrode and a second electrode, and a light efficiency improvement layer on the first and/or second electrode (Kang-KR, page 6 of 23, lines 3-5), wherein the light-efficiency-improvement layer comprises a compound represented by a formula (1) (Kang-MT, page 7 of 23, lines 31-33), and wherein the first electrode is an anode and the second electrode is a cathode (Kang-KR, page 9 of 23, lines 24-29). Kang teaches the organic material layer comprising a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer (Kang-MT, page 6 of 23, lines 18-20), wherein the compound is additionally contained in the hole transport layer (Kang-MT, page 6 of 23, lines 26-28). Kang teaches a host / dopant system may be used as a light emitting material (page 1 of 23, lines 37) and teaches examples wherein the dopant is a phosphorescent dopant (Kang-KR, page 16 of 23, lines 21-22), and wherein the electron transport region comprises an alkali metal (Kang-KR, page 16 of 23, lines 26-27). Kang teaches the device attains improved light emission efficiency and lowered driving voltage (page 1 of 23, lines 9-11). Kang teaches specific examples of the compound represented by formula (1) of Kang including compounds P-27 and P-28
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(Kang-KR, page 17).
Kang does not exemplify a compound that meets the claimed Formula 1. For example, the compounds of Kang differ from the claimed compounds in that the compounds of Kang (2) have the dibenzo groups substituted at the 3-position instead of the 4-position and (2) do not show wherein at least one of the central phenylene groups is fully deuterated (substituted with four deuteriums).
Regarding (1), Kang teaches that the dibenzo groups may be substituted at any positions (Kang-KR, page 15).
Given the general formula and teachings of Kang, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of the compounds wherein the dibenzo group are substituted at the 4-position instead of the 3-position. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by the general formula of Kang in order to pursue the known options within their technical grasp and would expect the isomeric compounds to be useful in the device of Kang and possess the properties taught by Kang. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP § 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP § 2144.09 II.
Regarding (2), Kang teaches the groups may be substituted with deuterium (Kang-KR, page 5 of 23, line 17).
Li teaches that a deuterated organic system has better thermal stability, and longer lifetime in optoelectronic devices (¶ [0009]) and deuterated organic semiconductor materials exhibit improved performance including brighter luminescence, better thermal stability, and longer lifetime compared to non-deuterated organic semiconductor materials (Abstract, ¶ [0023], and [0077]).
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 compounds of Kang including compounds P-27 and P-28 in the device of Kang to include at least one deuterium, based on the teachings of Li. The motivation for doing so would have been to obtain brighter luminescence, better thermal stability, and longer lifetime, as taught by Li.
Further, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to have fully deuterated at least one of the central phenylene groups, because each position would have been a choice from two options, H or D, which would have been a choice from a finite number of identified, predictable solutions of a compound useful in the hole transport layer of the device of Kang and possessing the beneficial properties taught by Kang. One of ordinary skill in the art would have been motivated to produce additional compounds represented by the general formula of Kang and being partially or fully deuterated based on the teachings of Li having the benefits as described above taught by Li in order to pursue the known options within their technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Two of the modified compounds of Kang in view of Li correspond to the claimed compounds 172 and 176:
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.
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Kang et al. KR-20140142923-A (hereinafter "Kang-KR" and see English language machine translation referred to herein as "Kang-MT") in view of Li et al. US-20020076576-A1 (hereinafter "Li") as applied to claim 4 above and further in view of Jang et al. US-20100289008-A1 ("Jang").
Regarding claim 5, Kang in view of Li discloses the device comprising the modified compound as described above with respect to claim 4.
Kang in view of Li does not teach wherein the hole transport region further comprises a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of less than about -3.5 eV.
Jang teaches an organic light emitting device having high efficiency can be obtained by forming a hole injecting and/or transporting layer of an organic light emitting device doping a material with a LUMO energy level of -4 eV or less in a material with a HOMO energy level of -4 eV or less (¶ [0009],¶ [0011]). Jang teaches specific examples of the material with a LUMO energy level of -4 eV or less include 2,3,5,6-tetrafluoro-7,7,8,8- tetracyanoquinodimethane (F4TCNQ) and hexaazatriphenylene-hexacarbonitrile (¶ [0036]), which comprise a cyano group, and specific examples of the material with a HOMO energy level of -4 eV or less include NPB (¶ [0033)).
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 device of Kang in view of Li by forming the hole transport layer comprising a material with a HOMO energy level of -4 eV or less and a material with a LUMO energy level of -4 eV or less, based on the teaching of Jang. The motivation for doing so would have been to obtain high efficiency, as taught by Jang.
Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over Kang et al. KR-20140142923-A (hereinafter "Kang-KR" and see English language machine translation referred to herein as "Kang-MT") in view of Li et al. US-20020076576-A1 (hereinafter "Li") as applied to claim 3 above and further in view of Funahashi et al. US-20030044640-A1 (hereinafter "Funahashi").
Regarding claim 6, Kang in view of Li teaches the device comprising the modified compound as described above with respect to claim 3.
Kang in view of Li does not specifically disclose wherein the dopant comprises a fluorescent dopant comprising a styryl-based compound.
Funahashi teaches a styryl compound of a general formula (1) (¶ [0007]) for use in the light emitting layer (¶ [0024]) and that when the styryl compound is added to a film of organic compounds, the obtained organic EL device has improved heat resistance and life, achieves a high efficiency of light emission due to improved transportation of holes and electrons and emits blue light of an improved purity (¶ [0006], ¶ [0081]).
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 the styryl compound of Funahashi in the emitting layer of the device of Kang in view of Li, based on the teaching of Funahashi. The motivation for doing so would have been to obtain an organic EL device having improved heat resistance and life, a high efficiency of light emission, and blue light of an improved purity, as taught by Funahashi.
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 Elizabeth M. Dahlburg whose telephone number is 571-272-6424. The examiner can normally be reached Monday through Thursday, 9 a.m. to 4 p.m. ET, and alternate Fridays.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached on 571-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ELIZABETH M. DAHLBURG/Primary Examiner, Art Unit 1786
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