US 12,441,935 B2
Organic electroluminescent device
Tae Hyung Kim, Seongnam-si (KR); HoCheol Park, Suwon-si (KR); Young Bae Kim, Hwaseong-si (KR); Chang Jun Lee, Ansan-si (KR); Eunjung Lee, Seoul (KR); and Youngmi Beak, Yongin-si (KR)
Assigned to SOLUS ADVANCED MATERIALS CO., LTD., Ilksan-si (KR)
Filed by SOLUS ADVANCED MATERIALS CO., LTD., Iksan-si (KR)
Filed on Sep. 27, 2022, as Appl. No. 17/953,510.
Application 17/953,510 is a continuation of application No. 16/742,060, filed on Jan. 14, 2020, granted, now 11,588,109.
Application 16/742,060 is a continuation of application No. 15/107,971, granted, now 10,573,822, issued on Feb. 25, 2020, previously published as PCT/KR2014/012888, filed on Dec. 26, 2014.
Claims priority of application No. 10-2013-0166103 (KR), filed on Dec. 27, 2013; and application No. 10-2014-0158154 (KR), filed on Nov. 13, 2014.
Prior Publication US 2023/0093216 A1, Mar. 23, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/00 (2023.01); H10K 50/11 (2023.01); H10K 50/13 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01); H10K 101/30 (2023.01); H10K 101/40 (2023.01)
CPC C09K 11/025 (2013.01) [C09K 11/06 (2013.01); H10K 50/00 (2023.02); H10K 85/342 (2023.02); H10K 85/622 (2023.02); H10K 85/626 (2023.02); H10K 85/654 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/13 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02); H10K 50/18 (2023.02); H10K 50/181 (2023.02); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02); H10K 2101/40 (2023.02)] 2 Claims
OG exemplary drawing
 
1. An organic electroluminescent device comprising:
an anode;
a cathode; and
one or more organic material layers interposed between the anode and the cathode,
wherein said one or more organic material layers comprise (a) a light emitting layer comprising a host material and a dopant material, (b) a lifetime enhancement layer comprising a bipolar compound, (c) an electron transporting layer, and (d) at least one layer selected from the group consisting of a hole injection layer, a hole transporting layer, and an electron injection layer,
wherein the lifetime enhancement layer is interposed between the light emitting layer and the electron transporting layer,
wherein the bipolar compound has both an electron withdrawal group (EWG) moiety and an electron donor group (EDG) moiety, and satisfies the following (a) to (d) conditions:
(a) an ionization potential [Ip(LEL)] is 5.5 eV or more,
(b) EHOMO−ELUMO>2.9 eV,
(c) triplet energy is 2.3 eV or more, and
(d) ΔEst<0.5 eV (ΔEst indicates a difference between singlet energy and triplet energy of the compound),
wherein the EWG moiety in the bipolar compound comprises a moiety represented by the following chemical formulae:

OG Complex Work Unit Chemistry
wherein the EDG moiety in the bipolar compound comprises a moiety in which the following Chemical Formula 1 and the following Chemical Formula 2 combine with each other to form a fused ring:

OG Complex Work Unit Chemistry
in Chemical Formula 1,
X1 is selected from the group consisting of O, S, Se, N(Ar), C(Ar2)(Ar3), and Si(Ar4)(Ar5),
Y1 to Y4 are the same as or different from each other, and are each independently N or C(R1), and in this case, one of Y1 and Y2, Y2 and Y3, or Y3 and Y4 forms a fused ring with the following Chemical Formula 2 wherein a plurality of R1's is the same as or different from each other,
X2 and X3 are the same as or different from each other, and are each independently N or C(R2) wherein a plurality of R2's is the same as or different from each other,
R1 and R2 and Ar1 to Ar5 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C1 to C40 alkyl group, a C2 to C40 alkenyl group, a C2 to C40 alkynyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkyl boron group, a C6 to C60 aryl boron group, a C1 to C40 phosphine group, a C1 to C40 phosphine oxide group, and a C6 to C60 arylamine group, and
the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkyl boron group, the aryl boron group, the phosphine group, the phosphine oxide group, and the arylamine group of R1 and R2 and Ar1 to Ar5 are each independently unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C1 to C40 alkyl group, a C2 to C40 alkenyl group, a C2 to C40 alkynyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkyl boron group, a C6 to C60 aryl boron group, a C1 to C40 phosphine group, a C1 to C40 phosphine oxide group, and a C0 to C60 arylamine group,

OG Complex Work Unit Chemistry
in Chemical Formula 2,
Y5 to Y10 are the same as or different from each other, and are each independently N or C(R3), and in this case, a plurality of R3's is the same as or different from each other, and these groups optionally form a fused ring with Chemical Formula 1,
X4 is selected from the group consisting of O, S, Se, N(Ar1), C(Ar2)(Ar3), and Si(Ar4)(Ar5), and in this case, a plurality of Ar1's to Ar5's is the same as or different from each other,
a plurality of R3 which does not form a fused ring, is the same as or different from each other, and is each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C1 to C40 alkyl group, a C2 to C40 alkenyl group, a C2 to C40 alkynyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkyl boron group, a C6 to C60 aryl boron group, a C1 to C40 phosphine group, a C1 to C40 phosphine oxide group, and a C0 to C60 arylamine group,
the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkyl boron group, the aryl boron group, the phosphine group, the phosphine oxide group, and the arylamine group of R3 are each independently unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C1 to C40 alkyl group, a C2 to C40 alkenyl group, a C2 to C40 alkynyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkyl boron group, a C6 to C60 aryl boron group, a C1 to C40 phosphine group, a C1 to C40 phosphine oxide group, and a C0 to C60 arylamine group,
wherein the EWG moiety is connected directly or indirectly to the fused ring formed by the combination of the Chemical Formula 1 and the Chemical Formula 2.