DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
All outstanding objections and rejections, except for those maintained below, are withdrawn in light of applicant's amendment filed on 6/18/2026.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior office action.
The new grounds of rejection set forth below are necessitated by applicant's amendment filed on 6/18/2026. In particular, original Claims 1 and 13 have been amended to recite new limitations not previously presented. Thus, the following action is properly made final.
Claim Objections
Claim 13 is objected to because of the following informalities: Claim 13 recites the phrase “when Ar21 is any one selected from among Formula 9B-3, 9B-5 and 9B-7”. Applicants are advised to amend this phrase to recite “when Ar21 is any one selected from among Formula 9B-3, 9B-5 or 9B-7”. Appropriate correction is required.
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 1-7, 9-10, and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Ma et al (US 2016/0240800) in view of Pflumm et al (2013/0053558).
Regarding claim 1, Ma et al discloses an organic light emitting device comprising first and second electrodes, i.e. an anode and a cathode, and an organic layer disposed between the anode and cathode (Abstract [0027]). The organic layer, i.e. an emitter layer, comprises a compound given by Formula 1 or 2 ([0027]). The compound has the following structure ([0078]):
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In the above compound, the group X is NRE, O, or S and the groups RA, RB1, Rc, RD, and RE are H ([0063]-[0064]). The recited group M is Pt, the recited group X1 is O, and the bond between O and Pt is a covalent bond; the recited group X2 is N.
The recited groups Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, and Y9 are C. The recited groups Y10 and Y11 are C. The bond between Y1 and Y10 is a double bond, the bond between Y1 and Y2 is a dingle bond, the bond between X2 and Y3 is a double bond, the bond between X2 and Y4 is a single bond, the bond between Y4 and Y5 is a double bond, the bond between Y5 and Y6 is a single bond, the bond between X3 and Y7 is a double bond, the bond between X3 and Y8 is a single bond, the bond between X4 and Y9 is a double bond, and the bond between X4 and Y11 is single bond. The bond between Y2 and Y3, the bond between Y6 and Y7, and Y8 and Y9 are single bonds.
The recited group CY1 is a C6 carbocyclic group; the recited group CY2 is a C6 carbocyclic group; and the recited group CY5 is a C3 heterocyclic group. The recited group CY4 is a C6 carbocyclic group, i.e. benzene, and the recited group X4 is C, and therefore not one of the heterocyclic groups recited for CY4 of the present. Furthermore, the recited group X3 is N and not C as required in the present claims.
However, the above compound is but one embodiment and attention is directed to Formula (1) of the reference ([0069]) which is given as:
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where the recited group CY4 is given by ring D and the recited group CY3 is given by ring C. In rings C and D, the groups X4 and X3 are disclosed as carbon or nitrogen ([0066]). Thus, the recited group CY3 can be benzene, i.e. the recited group X3 is C and the group CY3 is a C6 carbocyclic group.
Given that X4 can be N, ring D in the compound of the reference can be a heteroaryl as disclosed in Paragraph [0068] of the reference. The reference discloses that the term “heteroaryl” encompasses groups such as isoquinoline, i.e.
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From the above, it is clear that isoquinoline, corresponding to the recited ring CY4, is a pyridine group condensed with a benzene group.
From the discussion above, the recited groups CY5, CY2, CY3, and M form a 6-membered ring. The recited group X51 corresponds to the group X and is O or S. The recited integers a1, a2, a3, and a4 are zero (0).
The reference teaches all the claim limitations as set forth above. However, the reference does not disclose that the light emitting layer comprises a second compound given by Formula (2) as recited in the present claims.
Pflumm et al discloses an organic light emitting device, where the light emitting layer comprises the following matrix material, i.e. host compound (Abstract, [0088], Page 9 – Compound 9):
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This compound corresponds to the recited second compound represented by Formula (2):
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where:
a11 is zero (0), and therefore, L11 is not a pyrenylene group as recited in the present claims;
b11 is one (1); and
n11 is two (2).
In recited Formula (2), Ar11 corresponds to Formula 8C-18 of the claims:
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R801, R802, R804, R808, and R809 are methyl groups. R813 and R806 correspond to:
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where, as discussed above, a11 is zero (0); b11 is one (1); n11 is one (1); R11 is a phenyl group, i.e. a hole transport group; and in Formula 8C-18 the remaining R-groups are hydrogen.
The reference discloses that utilizing the compound provides a low operating voltage, good efficiencies, and long lifetimes ([0130]).
Given that both Ma et al and Pflumm et al are drawn to organic light emitting device comprising electron transport layers, and given that Ma et al does not explicitly prohibit other ingredients from being present in the light emitting layer, in light of the particular advantages provided by the use and control of the compound as taught by Pflumm et al, it would therefore have been obvious to one of ordinary skill in the art to include such compounds in the light emitting layer of the organic light emitting device disclosed by Ma et al in order to improve electroluminescent properties and obtain a device having a low operating voltage, good efficiency and a long lifetime with a reasonable expectation of success.
Regarding claim 2, the combined disclosures of Ma et al and Pflumm et al teach all the claim limitations as set forth above. From the discussion above, in Ma et al, the recited ring CY1 is a six (6) membered ring; the recited group CY2 is six (6) membered ring; the recited group CY3 is a six (6) membered ring; and the recited group CY5 is a 5-membered ring. The 6-membered rings are benzene and pyridine, and the 5-membered ring is an imidazole ring, i.e. the group X in the compound of Ma et al is N.
Regarding claim 3, the combined disclosures of Ma et al and Pflumm et al teach all the claim limitations as set forth above. From the discussion above, the recited groups CY1 and CY2 are benzene rings; the recited group CY4 is an isoquinoline group; and the recited group CY3 is benzene.
Regarding claim 4, the combined disclosures of Ma et al and Pflumm et al teach all the claim limitations as set forth above. Given that the compound of Formula 1 in claim 1 does not require the recited groups L1 to L4 and L7, Ma et al discloses the compound as recited in the present claims.
Regarding claim 5, the combined disclosures of Ma et al and Pflumm et al teach all the claim limitations as set forth above. Given that the compound of Formula 1 in claim 1 does not require the recited groups R1 to R4, R7 and R8, Ma et al discloses the compound as recited in the present claims.
Regarding claim 6, the combined disclosures of Ma et al and Pflumm et al teach all the claim limitations as set forth above. As discussed above, Ma et al discloses that the recited group X51 is O or S.
Regarding claim 7, the combined disclosures of Ma et al and Pflumm et al teach all the claim limitations as set forth above. As discussed above, in the compound disclosed by Ma et al, the recited group X51 is O. From the discussion above, the recited groups CY1 and CY2 are benzene rings; the recited group CY3 is benzene; and the recited group CY4 is an isoquinoline. Thus, Ma et al discloses a compound given by recited Formula 1-2A of the claim.
Regarding claim 9, the combined disclosures of Ma et al and Pflumm et al teach all the claim limitations as set forth above. Given that L11 is not required by the present claims, Pflumm et al discloses a compound encompassed by the present claims.
Regarding claim 10, the combined disclosures of Ma et al and Pflumm et al teach all the claim limitations as set forth above. As discussed above, in the compound disclosed by Pflumm et al R11 is a phenyl group.
Regarding claim 12, the combined disclosures of Ma et al and Pflumm et al teach all the claim limitations as set forth above. Additionally, Pflumm et al discloses that the amount of the compound as a matrix or host material is between 50.0 and 99.9 vol. % of the emitter layer ([0109]). Accordingly, it is clear that the amount of the matrix material or host compound can be greater than that of the dopant, i.e. recited first compound.
Claims 13-15 are rejected under 35 U.S.C. 103 as being unpatentable over Ma et al (US 2016/0240800) in view of Nishimura et al (US 2010/0171109) and Kawamura et al (US 2012/0153268).
Regarding claim 13, Ma et al discloses an organic light emitting device comprising first and second electrodes, i.e. an anode and a cathode, and an organic layer disposed between the anode and cathode (Abstract [0027]). The organic layer, i.e. an emitter layer, comprises a compound given by Formula 1 or 2 ([0027]). The compound has the following structure ([0078]):
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In the above compound, the group X is NRE, O, or S and the groups RA, RB1, Rc, RD, and RE are H ([0063]-[0064]). The recited group M is Pt, the recited group X1 is O, and the bond between O and Pt is a covalent bond; the recited group X2 is N.
The recited groups Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, and Y9 are C. The recited groups Y10 and Y11 are C. The bond between Y1 and Y10 is a double bond, the bond between Y1 and Y2 is a dingle bond, the bond between X2 and Y3 is a double bond, the bond between X2 and Y4 is a single bond, the bond between Y4 and Y5 is a double bond, the bond between Y5 and Y6 is a single bond, the bond between X3 and Y7 is a double bond, the bond between X3 and Y8 is a single bond, the bond between X4 and Y9 is a double bond, and the bond between X4 and Y11 is single bond. The bond between Y2 and Y3, the bond between Y6 and Y7, and Y8 and Y9 are single bonds.
The recited group CY1 is a C6 carbocyclic group; the recited group CY2 is a C6 carbocyclic group; and the recited group CY5 is a C3 heterocyclic group. The recited group CY4 is a C6 carbocyclic group, i.e. benzene, and the recited group X4 is C, and therefore not one of the heterocyclic groups recited for CY4 of the present. Furthermore, the recited group X3 is N and not C as required in the present claims.
However, the above compound is but one embodiment and attention is directed to Formula (1) of the reference ([0069]) which is given as:
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where the recited group CY4 is given by ring D and the recited group CY3 is given by ring C. In rings C and D, the groups X4 and X3 are disclosed as carbon or nitrogen ([0066]). Thus, the recited group CY3 can be benzene, i.e. the recited group X3 is C and the group CY3 is a C6 carbocyclic group.
Given that X4 can be N, ring D in the compound of the reference can be a heteroaryl as disclosed in Paragraph [0068] of the reference. The reference discloses that the term “heteroaryl” encompasses groups such as isoquinoline, i.e.
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From the above, it is clear that isoquinoline, corresponding to the recited ring CY4, is a pyridine group condensed with a benzene group.
From the discussion above, the recited groups CY5, CY2, CY3, and M form a 6-membered ring. The recited group X51 corresponds to the group X and is O or S. The recited integers a1, a2, a3, and a4 are zero (0).
The reference teaches all the claim limitations as set forth above. However, the reference does not disclose that the light emitting layer comprises a second compound given by Formula (2) as recited in the present claims.
Nishimura et al discloses an organic light emitting device comprising a light emitting layer, where the light emitting layer comprises a phosphorescent dopant and a phosphorescent host (Abstract). The phosphorescent host has a polycyclic fused aromatic skeleton with the following formula (Abstract, [0026], [0035] and Page 8):
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This compound corresponds to the recited second compound represented by Formula (2):
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where n11 is two (2). In recited Formula (2), Ar11 corresponds to Formula 8B-3 of the claims:
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where R811 and R805 are:
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where a11 is zero (0); b11 is one (1); and R11 is naphthyl, i.e. a hole transport group. In Formula 8B-3, the remaining R-groups are H.
Alternatively, the reference discloses the following phosphorescent host with a polycyclic fused aromatic skeleton ([0038]):
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This compound corresponds to the recited second compound represented by Formula (2):
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where n11 is two (2). In recited Formula (2), Ar11 corresponds to Formula 8B-4 of the claims:
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where R812 and R803 are:
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where a11 is zero (0); b11 is one (1); and R11 is phenyl, i.e. a hole transport group. In Formula 8B-4, the remaining R-groups are H.
Alternatively, the reference discloses the following phosphorescent host with a polycyclic fused aromatic skeleton ([0042]):
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This compound corresponds to the recited second compound represented by Formula (2):
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where n11 is two (2). In recited Formula (2), Ar11 corresponds to Formula 8B-5 of the claims:
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where R801 and R804 are:
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where a11 is zero (0); b11 is one (1); and R11 is phenyl, i.e. a hole transport group. In Formula 8B-5, the remaining R-groups are H.
Alternatively, the reference discloses the following phosphorescent host with a polycyclic fused aromatic skeleton ([0049]):
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This compound corresponds to the recited second compound represented by Formula (2):
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where n11 is one (1). In recited Formula (2), Ar11 corresponds to Formula 8B-10 of the claims:
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where R809 is:
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where a11 is one(1); b11 is one (1); L11 is a phenylene group, and R11 is phenyl, i.e. a hole transport group. In Formula 8B-10, the remaining R-groups are H.
The reference discloses that the phosphorescent host has high stability so that the singlet and triplet energy can be transferred smoothly, resulting in enhanced luminous efficiency and long lifetime ([0114]-[0115]).
Given that both Ma et al and Nishimura et al are drawn to organic light emitting device comprising electron transport layers, and given that Ma et al does not explicitly prohibit other ingredients from being present in the electron transport layer, in light of the particular advantages provided by the use and control of the compound as taught by Nishimura et al, it would therefore have been obvious to one of ordinary skill in the art to include such compounds in the electron transport layer of the organic light emitting device disclosed by Ma et al with a reasonable expectation of success.
The combined disclosures of Ma et al and Nishimura et al teach all the claim limitations as set forth above. However, Ma et al does not disclose that the organic layer comprises a third compound given by Formula (3) as recited in the present claims.
Kawamura et al discloses an organic light emitting device where a barrier layer between the electron transporting layer and the emitting layer comprises the following compound (Abstract, [0096], and Page 16):
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This compound corresponds to recited third compound represented by Formula 3, i.e.
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where:
n21 is one (1);
a21 is one (1);
b21 is one (1); and
L21 is an unsubstituted benzene.
Ar21 is represented by Formula 9B-16, i.e.
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where R911 corresponds to:
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where, as discussed above, a21 is one (1), b21 is one (1); n21 is one (1); and L21 is an unsubstituted benzene. In Formula 9B-16 R21 is a substituted benzimidazolyl group, i.e. an electron transport group, and the remaining R-groups are H.
The reference discloses that the use of the compound improves electron injection capability from the cathode ([0049]).
Given that both Ma et al and Kawamura et al are drawn to organic light emitting device comprising electron transport layers, in light of the particular advantages provided by the use and control of the compound as taught by Kawamura et al, it would therefore have been obvious to one of ordinary skill in the art to modify the device disclosed by Ma et al to include a barrier layer comprising the compound disclosed by Kawamura et al in order to improve electron capability of the cathode with a reasonable expectation of success.
Regarding claim 14, the combined disclosures of Ma et al, Nishimura et al, and Kawamura et al teach all the claim limitations as set forth above. From the discussion above, it is clear that the recited compound as disclosed by Nishimura et al is different from the recited third compound taught by Kawamura et al.
Regarding claim 15, the combined disclosures of Ma et al, Nishimura et al, and Kawamura et al teach all the claim limitations as set forth above. As discussed above, in the compound disclosed by Kawamura et al, R21 is a benzimidazolyl group substituted with a C6 aryl group.
Response to Arguments
Applicant's arguments filed 6/18/2026 have been fully considered but they are not persuasive.
In light of the amendments to the claims, the 35 U.S.C. 103 rejections set forth in the previous Office Action are withdrawn.
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 extension fee 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 date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALEXANDER C. KOLLIAS whose telephone number is (571)-270-3869. The examiner can normally be reached on Monday-Friday, 8:00AM – 5:00 PM EST.
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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/ALEXANDER C KOLLIAS/Primary Examiner, Art Unit 1786
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