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 .
Status of Claims
Claims 1, 5, 8, and 17 are amended due to Applicant's amendment dated 02/11/2026. Claims 1, 5-12, and 14-21 are pending.
Response to Amendment
The objection to claims 1, 8, and 17 as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 02/11/2026.
The rejection of claims 1, 5-12, and 14-21 under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 02/11/2026. The rejection is withdrawn.
The rejection of claims 1, 6-12, and 14 under 35 U.S.C. 103 as being unpatentable over Lee (US 2015/0336937 A1) in view of Shin (WO 2010/114264 A1) is not overcome due to the Applicant’s amendment dated 02/11/2026. The rejection is maintained.
The rejection of claim 5 under 35 U.S.C. 103 as being unpatentable over Lee in view of Shin and Fennimore (US 2017/0200893 A1) is not overcome due to the Applicant’s amendment dated 02/11/2026. The rejection is maintained.
The rejection of claims 15-20 under 35 U.S.C. 103 as being unpatentable over Lee in view of Shin and Kim (US 2014/0197386 A1) is not overcome due to the Applicant’s amendment dated 02/11/2026. The rejection is maintained.
The rejection of claim 21 under 35 U.S.C. 103 as being unpatentable over Lee in view of Shin, Kim, and Adamovich (US 2014/0197389 A1) is not overcome due to the Applicant’s amendment dated 02/11/2026. The rejection is maintained.
Response to Arguments
Applicant’s arguments on pages 43-52 of the reply dated 02/11/2026 with respect to the rejection of claims 1, 5-12, and 14-21 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –On pages 43-52, Applicant argues the claimed compounds provide unexpected and superior results over the prior art. In particular, Applicant argues the position of the substituents on the core structure is critical and that the condensed carbazole substituent at the dibenzofuran ring in Chemical Formula 3-6 combined with the specific position of the N-Het group on the phenyl ring having the condensed carbazole substituent provides unexpected and superior performance with respect to driving voltages, light efficiency, and operational lifetime in OLED devices. Applicant points to Tables 8-9 of the instant specification and Tables 8-9 of the Declaration filed 02/11/2026 for support in which devices comprising compounds 124 and 8 of Lee and compound 82 of Shin are compared to devices of Examples 1 to 5 comprising inventive compounds 1-3, 6, and 11, respectively.
PNG
media_image1.png
92
350
media_image1.png
Greyscale
PNG
media_image2.png
106
92
media_image2.png
Greyscale
PNG
media_image3.png
113
88
media_image3.png
Greyscale
Examiner's response –It should be noted that compounds 1 and 6 read on the claimed Chemical Formula 1-2 wherein: R11 to R15, R18, and Rb are all hydrogen or adjacent two groups among R11 to R14 of Chemical Formula 1-2 bond to each other to form an unsubstituted benzene ring; and N-Het is a triazine ring. However, claim 1 recites when R11 to R15, R18, and Rb of Chemical Formula 1-2 are all hydrogen or adjacent two groups among R11 to R14 of Chemical Formula 1-2 bond to each other to form an unsubstituted benzene ring, N-Het is selected from groups that do not include triazine. Accordingly, compounds 1 and 6 (and therefore, Examples 1 and 4) are outside the scope of claim 1.
It should also be noted that while Applicant claims to use Lee’s compound 8 in a comparative device, Applicant actually uses Lee’s compound 7 (see pg. 17 of Lee and pg. 48 of the remarks). The difference between these compounds being that compound 8 comprises a pyrimidine in the location of the claimed N-Het and compound 7 comprises a triazine in the location of the claimed N-Het. Accordingly, no data is provided for a comparative device comprising Lee’s compound 8. Lee’s compound 124 and compounds 7-8 are reproduced below.
124:
PNG
media_image4.png
235
262
media_image4.png
Greyscale
7:
PNG
media_image5.png
211
242
media_image5.png
Greyscale
8:
PNG
media_image6.png
211
240
media_image6.png
Greyscale
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).
Commensurate in Scope
As discussed in greater detail in the rejection below, Lee teaches compound 8 and compound 124 (see structures on pgs. 17 and 35 of Lee). As shown by the structures above, compound 8 comprises pyrimidine and compound 124 comprises dibenzothienopyrimidine, which are within the scope of the variable N-Het of the claimed Chemical Formulae 3 to 6. As shown by the structures above, inventive compounds 1-3, 6, and 11 only comprise triazine in the location of N-Het. As there are no results of inventive compounds in which N-Het is selected as pyrimidine or dibenzothienopyrimidine (as shown by the compounds in Lee), it is unclear if the same results discussed by Applicant would be present.
As claim 1 claims a broad heterocyclic compound represented by one of the Chemical Formulae 3 to 6 wherein N-Het is a C2 to C60 monocyclic or polycyclic heterocyclic group comprising one or more Ns, but the compounds of the instant examples only include structures wherein N-Het is a triazine group, the results are not commensurate in scope with the claims.
Additionally, the data shown in Tables 8-9 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 light emitting layer of a device (see instant pgs. 134-135), whereas claim 1 is directed to a compound. The improved properties relating to driving voltages, light efficiency, and operational lifetimes are shown when the compound is used in a light emitting layer of an OLED with a particular phosphorescent dopant (see instant pg. 135). 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 or with other dopants.
Applicant's argument –On pages 44-45, Applicant argues a person of ordinary skill in the art would not have been motivated to selectively extract only the dibenzocarbazole substituent from Shin’s compound 82 and then substitute it for the carbazole moiety in Lee’s compound 124 or compound 8.
Examiner's response –As discussed in the rejection below, Lee teaches compounds 124 and compound 8 which each include a carbazole group. Shin teaches compounds of Chemical Formula 1 achieve superior luminescence efficiency, excellent color purity and life property, and provide a device with superior operation life (¶ [1]-[4] and [15]). In Chemical Formula 1, rings A and B are not both monocyclic aromatic rings (¶ [19]). That is, the moiety
PNG
media_image7.png
36
44
media_image7.png
Greyscale
of Chemical Formula 1 cannot be carbazole as this would include monocyclic aromatic rings in the locations of rings A and B. Shin teaches examples of compounds represented by Chemical Formula 1 including compound 82 (pg. 13).
Chemical Formula 1:
PNG
media_image7.png
36
44
media_image7.png
Greyscale
82:
PNG
media_image8.png
102
115
media_image8.png
Greyscale
Lee’s Compounds 124 and 8 read on Shin’s Chemical Formula 1 except wherein it contains monocyclic aromatic rings in the locations of both A and B (i.e., a carbazole group). Therefore, to obtain the benefits discussed by Shin, it would have been obvious to substitute the carbazole group of compound 124 (or alternatively compound 8) with dibenzocarbazole, as shown in Shin’s compound 82, to arrive at a compound having the structure of Shin’s Chemical Formula 1. The motivation for doing so would have been to provide a compound with superior luminescence efficiency, excellent color purity and life property, and to provide a device with superior operation life, as taught by Shin.
Specifically, it would have been obvious for one of ordinary skill to look to the dibenzocarbazole group of Shin’s compound 82, because this would have been a specific example of a moiety comprising the structure
PNG
media_image7.png
36
44
media_image7.png
Greyscale
taught by Shin, which would have been a choice from a finite number of identified, predictable solutions of a moiety having the structure of
PNG
media_image7.png
36
44
media_image7.png
Greyscale
that would be useful in a compound having the structure of Shin’s Chemical Formula 1 and possessing the benefits taught by Shin. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Shin’s Chemical Formula 1 having the benefits taught by Shin in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
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, 6-12, and 14 is rejected under 35 U.S.C. 103 as being unpatentable over Lee (US 2015/0336937 A1) in view of Shin (WO 2010/114264 A1).
Regarding claims 1, 6-11, and 14, Lee teaches an organic light-emitting device including a carbazole compound represented by Formula 1, wherein the device obtains improved consumption power, efficiency, luminance, and lifetime characteristics (abstract; ¶ [0141]). The device includes an anode, a hole transport layer, an emission layer including a host represented by Formula 1 and a dopant, an electron transport layer, an electron injection layer, and a cathode (¶ [0138]-[0140], [0146]-[0149], and [0332]-[0335]). Lee teaches examples of compounds represented by Formula 1 including compound 124 or alternatively, compound 8 (pgs. 17 and 35).
Formula 1:
PNG
media_image9.png
147
358
media_image9.png
Greyscale
124:
PNG
media_image10.png
237
264
media_image10.png
Greyscale
8:
PNG
media_image11.png
214
241
media_image11.png
Greyscale
Compound 124 fails to include the dibenzothienopyrimidine group in position 9 of the dibenzofuran ring rather than position 8. Similarly, Compound 8 fails to include the pyrimidine group in position 9 of the dibenzofuran ring rather than position 8. However, Lee does teach these groups may be in any of positions R2 to R4 (¶ [0016]).
Therefore, given the general formula and teachings of Lee, 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 compound 124 wherein the dibenzothienopyrimidine group is provided in position 9 of the dibenzofuran ring. It alternatively 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 compound 8 wherein the pyrimidine group is provided in position 9 of the dibenzofuran ring. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Lee’s Formula 1 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful in the device of Lee and possess the properties taught by Lee. 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.
The modified compound 124 fails to read on the claimed Chemical Formula 3 as it comprises carbazole rather than benzocarbazole. Similarly, the modified compound 8 fails to read on the claimed Chemical Formula 3 as it comprises carbazole rather than benzocarbazole. However, Lee does teach R11 and R12 may be selected from a C2-C60 alkenyl group, among others (¶ [0015]).
Shin teaches organic electroluminescent compounds represented by Chemical Formula 1 having superior luminescence efficiency and excellent color purity and life property, which provide an OLED with very superior operation life (¶ [1]-[4] and [15]). In Chemical Formula 1, rings A and B are not both monocyclic aromatic rings (¶ [19]). Shin teaches compounds represented by Chemical Formula 1 may be used as a host in an OLED (see Table 2 on pg. 28). Shin teaches examples of compounds represented by Chemical Formula 1 including compound 82 (pg. 13).
Chemical Formula 1:
PNG
media_image7.png
36
44
media_image7.png
Greyscale
82:
PNG
media_image8.png
102
115
media_image8.png
Greyscale
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the carbazole group of compound 124 with dibenzocarbazole, as shown in Shin’s compound 82, based on the teaching of Shin. Alternatively, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the carbazole group of compound 8 with dibenzocarbazole, as shown in Shin’s compound 82, based on the teaching of Shin. The motivation for doing so would have been to provide a compound with superior luminescence efficiency and excellent color purity and life property and to provide a device with very superior operation life, as taught by Shin.
The modified compound 124 reads on Shin’s Chemical Formula 1 wherein ring A and ring B each represent a polycyclic aromatic ring, R1 represents a substituted C10 heteroaryl, and R2 and R3 each represent hydrogen (see Shin, ¶ [17]-[20]). Similarly, the modified compound 8 reads on Shin’s Chemical Formula 1 wherein ring A and ring B each represent a polycyclic aromatic ring, R1 represents a substituted C10 heteroaryl, and R2 and R3 each represent hydrogen (see Shin, ¶ [17]-[20]). Accordingly, the modified compound 124 and the modified compound 8 are expected to obtain the benefits of Shin.
The modified compound 124 has the structure below and is reproduced in comparison to the claimed Chemical Formula 3. Additionally, the modified compound 124 reads on the claimed compound 311 (claim 8).
Modified 124:
PNG
media_image12.png
138
123
media_image12.png
Greyscale
Chemical Formula 3:
PNG
media_image13.png
270
349
media_image13.png
Greyscale
The modified compound 124 reads on the claimed Chemical Formula 3 wherein:
N-Het is a substituted C10 polycyclic heterocyclic group comprising two Ns, and is:
A benzo[4,5]thieno[3,2-d]pyrimidine group substituted with a phenyl group;
L is a direct bond;
a is 1;
R5 and R6 are each hydrogen;
b is 2, and c is 4;
PNG
media_image14.png
146
142
media_image14.png
Greyscale
is represented by Chemical Formula 1-2;
R11, R14, R15, and R18 are each hydrogen, and R12 and R13 bond to each other to form an unsubstituted benzene ring; and
m is 4.
The modified compound 8 reads on the Chemical Formula 3 in the same way as described above except wherein N-Het is a substituted C4 monocyclic heterocyclic group comprising two Ns, and further represented by Chemical Formula 2-1 wherein X1 and X5 are each N (claim 6) and represented by
PNG
media_image15.png
107
130
media_image15.png
Greyscale
(claim 7).
Regarding claim 12, Lee in view of Shin teach the device of claim 9 including the modified compound 124 (or alternatively the modified compound 8), as described above.
The device fails to include the modified compound 124 in an electron blocking layer, a hole blocking layer, an electron injection layer, or an electron transport layer. Similarly, the device fails to include the modified compound 8 in an electron blocking layer, a hole blocking layer, an electron injection layer, or an electron transport layer. However, Lee does teach the carbazole compound of Formula 1 may be used in the electron transport region (including an electron transport layer and an electron injection layer) (¶ [0142]).
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 modified compound 124 (or alternatively the modified compound 8) in the electron transport layer or the electron injection layer, because one of ordinary skill in the art would reasonably have expected the elements of a compound represented by Formula 1 and the electron injection and transport layer to predictably maintain their respective properties or functions after they have been combined, and this would have been combining prior art elements according to known methods to yield predictable results. See MPEP 2143.I.(A).
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Lee (US 2015/0336937 A1) in view of Shin (WO 2010/114264 A1) as applied to claim 1 above, and further in view of Fennimore (US 2017/0200893 A1).
Regarding claim 5, Lee in view of Shin teach the modified compound 124 (or alternatively the modified compound 8), as described above with respect to claim 1.
Lee fails to teach the modified compound 124 is 10-100% deuterated. Similarly, Lee fails to teach the modified compound 8 is 10-100% deuterated. However, Lee does teach substituents may be selected as deuterium (¶ [0015] and [0300]).
Fennimore teaches deuterated materials can be less susceptible to degradation by holes, electrons, or excitons, have greater processing tolerance, and can potentially improve device lifetime compared to their non-deuterated analogs (¶ [0098]). Fennimore teaches deuterated materials may be 10-100% deuterated (¶ [0097]).
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 deuterate the modified compound 124 (or alternatively, the modified compound 8), wherein the deuterium content is 10-100%, to provide a compound that is less susceptible to degradation by holes, electrons, or excitons, has greater processing tolerance, and can potentially improve device lifetime, as taught by Fennimore.
Claims 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over Lee (US 2015/0336937 A1) in view of Shin (WO 2010/114264 A1) as applied to claim 9 above, and further in view of Kim (US 2014/0197386 A1).
Regarding claims 15-20, Lee in view of Shin teach the device including the modified compound 124 (or alternatively the modified compound 8) as a host in the emission layer, as described above with respect to claim 9.
Lee fails to teach the device includes a second host represented by the claimed Chemical Formula 2. However, Lee does teach the emission layer may include two hosts (¶ [0187]).
Kim teaches an organic optoelectronic device having high efficiency and long life-span by including an emission layer comprising hosts of a first compound represented by Chemical Formula A-1 and a second compound represented by Chemical Formula B-1, wherein the compound represented by Chemical Formula A-1 and the compound represented by Chemical Formula B-1 are mixed in a ratio of about 3:7 to about 7:3 (¶ [0021]-[0023] and [0133]-[0134]; Table 1 on pg. 46). Examples of compounds represented by Chemical Formula B-1 including Chemical Formula I-3 (pg. 13).
A-1:
PNG
media_image16.png
132
130
media_image16.png
Greyscale
B-1:
PNG
media_image17.png
110
310
media_image17.png
Greyscale
The modified compound 124 reads on Kim’s Chemical Formula A-1 wherein Ar1 is a substituted C10 heteroaryl group, L1 is an unsubstituted C12 heteroarylene group, n1 is 1, and R1 to R4 are each hydrogen (see Kim, ¶ [0023]-[0028]). Similarly, the modified compound 8 reads on Kim’s Chemical Formula A-1 wherein Ar1 is a substituted C4 heteroaryl group, L1 is an unsubstituted C12 heteroarylene group, n1 is 1, and R1 to R4 are each hydrogen (see Kim, ¶ [0023]-[0028]).
Therefore, as Lee’s modified compound 124 and modified compound 8 each read on Kim’s Chemical Formula A-1, 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 a second host represented by a compound of Kim’s Chemical Formula B-1 in the emission layer, wherein the modified compound 124 (or alternatively the modified compound 8) and the compound represented by Kim’s Chemical Formula B-1 are mixed in a ratio of about 3:7 to about 7:3, as taught by Kim. The motivation for doing so would have been to provide a device with high efficiency and long life-span, as taught by Kim.
In particular, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select Kim’s Chemical Formula I-3 as the second host, because it would have been choosing from a list of exemplified compounds taught by Kim suitable as a compound represented by Chemical Formula B-1, and this would have been a choice from a finite number of identified, predictable solutions of a compound useful in the emission layer of the device of Lee and possessing the benefits taught by Kim above. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Kim’s Chemical Formula B-1 having the benefits taught by Kim in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Kim’s Chemical Formula I-3 is reproduced below in comparison to the claimed Chemical Formula 2.
I-3:
PNG
media_image18.png
348
250
media_image18.png
Greyscale
Chemical Formula 2:
PNG
media_image19.png
203
306
media_image19.png
Greyscale
Kim’s Chemical Formula I-3 reads on the claimed Chemical Formula 2 and 10 (claims 15-16 and 18) wherein:
Ar1 is an unsubstituted C12 aryl group;
R51 to R55, R57, and R58 are each hydrogen, and R56 is a substituted C12 heteroaryl group, wherein the substituent is a C6 monocyclic aryl that is further substituted with a C6 monocyclic aryl;
R61 to R70 are each hydrogen; and
Ar2 and Ar3 are each an unsubstituted C12 aryl group.
Additionally, Kim’s Chemical Formula I-3 reads on the claimed compound 1-2 (claim 17).
Per claim 19, as discussed above, wherein the modified compound 124 (or alternatively the modified compound 8) and the compound represented by Kim’s Chemical Formula B-1 are mixed in a ratio of about 3:7 to about 7:3. 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.
Per claim 20, Lee teaches in the formation of the device, the first electrode (anode) is formed on a substrate, the organic layer including the emission layer is disposed on the first electrode, and the second electrode (cathode) is disposed on the organic layer (¶ [0152], [0154], and [0284]). As discussed above, the emission layer includes the modified compound 124 (or alternatively the modified compound 8) and Kim’s Chemical Formula I-3.
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over Lee (US 2015/0336937 A1) in view of Shin (WO 2010/114264 A1) and Kim (US 2014/0197386 A1) as applied to claim 20 above, and further in view of Adamovich (US 2014/0197389 A1).
Regarding claim 21, Lee in view of Shin and Kim teach the device including the modified compound 124 (or alternatively the modified compound 8) and Chemical Formula I-3 as first and second hosts in the emission layer, as described above with respect to claim 20.
While Lee teaches the emission layer may be formed using vacuum deposition (¶ [0184]), Lee in view of Shin and Kim fail to specifically teach the two compounds are pre-mixed before vacuum deposition.
Adamovich teaches an emissive layer comprising multiple host compounds wherein the host compounds may be pre-mixed and then deposited by vacuum thermal evaporation (abstract and ¶ [0049]).
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 pre-mix the modified compound 124 (or alternatively the modified compound 8) and Chemical Formula I-3 prior to deposition by vacuum thermal evaporation, because one of ordinary skill in the art would reasonably have expected the emission layer, the modified compound 124, and Chemical Formula I-3 to predictably maintain their respective properties or functions after the emission layer has been formed according to Adamovich, and this would have been combining prior art elements according to known methods to yield predictable results. See MPEP 2143.I.(A).
Conclusion
THIS ACTION IS MADE FINAL. 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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
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.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/BRAELYN R WATSON/Examiner, Art Unit 1786
Prosecution Insights