US 12,219,872 B2
Organic electroluminescent element
Yuta Hirayama, Tokyo (JP); Takeshi Yamamoto, Tokyo (JP); Shunji Mochizuki, Tokyo (JP); Shuichi Hayashi, Tokyo (JP); Se-Jin Lee, Cheongju-si (KR); Oun-Gyu Lee, Cheongju-si (KR); and Bong-Ki Shin, Cheongju-si (KR)
Assigned to Hodogaya Chemical Co., Ltd., Tokyo (JP); and SFC CO., LTD., Cheongju-si (KR)
Appl. No. 17/417,267
Filed by Hodogaya Chemical Co., Ltd., Tokyo (JP); and SFC CO., LTD., Cheongju-si (KR)
PCT Filed Dec. 18, 2019, PCT No. PCT/JP2019/049533
§ 371(c)(1), (2) Date Jun. 22, 2021,
PCT Pub. No. WO2020/137724, PCT Pub. Date Jul. 2, 2020.
Claims priority of application No. 2018-241387 (JP), filed on Dec. 25, 2018.
Prior Publication US 2022/0077403 A1, Mar. 10, 2022
Int. Cl. H10K 50/11 (2023.01); H01L 51/00 (2006.01); H10K 59/00 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/6572 (2023.02) [H10K 85/626 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 19 Claims
OG exemplary drawing
 
1. An organic electroluminescent element comprising at least an anode, a hole transport layer, a luminous layer, an electron transport layer, a cathode and a capping layer in this order,
wherein the capping layer comprises an arylamine compound represented by a following general formula (1);
the luminous layer comprises either or both of a heterocyclic compound having a fused ring structure represented by a following general formula (2a) and a heterocyclic compound having a fused ring structure represented by a following general formula (3a-2); and
the hole transport layer comprises an arylamine compound having two triphenylamine structures in a molecule and having a structure in which the two triphenylamine structures are linked by a single bond or a divalent group not containing a hetero atom,

OG Complex Work Unit Chemistry
wherein, in the formula (1),
Ar1, Ar2, Ar3, and Ar4 may be the same or different from each other and represent any one selected from a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group; and
n represents an integer of 0 to 4,
wherein at least one of Ar1, Ar2, Ar3, and Ar4 is a monovalent group represented by a structural formula (B) or a structural formula (B′), or has the monovalent group as a substituent,

OG Complex Work Unit Chemistry
wherein, in the formula (B),
R1 to R4 may be the same or different from each other and represent a linking group as a binding site, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a trimethylsilyl group, a triphenylsilyl group, a linear or branched alkyl group having 1 to 6 carbon atoms that may have a substituent group, a cycloalkyl group having 5 to 10 carbon atoms that may have a substituent group, a linear or branched alkenyl group having 2 to 6 carbon atoms that may have a substituent group, a linear or branched alkoxy group having 1 to 6 carbon atoms that may have a substituent group, a cycloalkyloxy group having 5 to 10 carbon atoms that may have a substituent group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group;
Ar5 and Ar6 may be the same or different from each other and represent a linking group as a binding site, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group;
X represents a carbon atom or a nitrogen atom; and Y represents any one selected from a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom,
however, when Y is an oxygen atom or a sulfur atom, Y has no Ar6; when X and Y are nitrogen atoms, X or Y has no Ar5 or Ar6; the case when X and Y are both carbon atoms; and the case when X is nitrogen atoms and Y is oxygen atoms, and the case when X is nitrogen atoms and Y is sulfur atoms are excluded; and
with the same substituted benzene ring, R1 to R4 may be bonded to each other, via a single bond, substituted or unsubstituted methylene group, substituted or unsubstituted amino group, oxygen atom or sulfur atom to form a ring,

OG Complex Work Unit Chemistry
wherein, in the formula (B′),
R3, R4 and R23 to R26 may be the same or different from each other and represent a linking group, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a trimethylsilyl group, a triphenylsilyl group, a linear or branched alkyl group having 1 to 6 carbon atoms that may have a substituent group, a cycloalkyl group having 5 to 10 carbon atoms that may have a substituent group, a linear or branched alkenyl group having 2 to 6 carbon atoms that may have a substituent group, a linear or branched alkyloxy group having 1 to 6 carbon atoms that may have a substituent group, a cycloalkyloxy group having 5 to 10 carbon atoms that may have a substituent group, and a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group;
Ar5 and Ar6 may be the same or different from each other and represent a linking group as a binding site, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group;
X represents a carbon atom or a nitrogen atom; and Y represents any one selected from a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and
however, when Y is an oxygen atom or a sulfur atom, Y has no Ar6; and when X and Y are nitrogen atoms, X or Y has no Ar5 or Ar6; the case when X and Y are carbon atoms; and the case when X is nitrogen atoms and Y is oxygen atoms, and the case when X is nitrogen atoms and Y is sulfur atoms are excluded; and
with the same substituted benzene ring, R3, R4 and R23 to R26 may be bonded to each other, via a single bond, substituted or unsubstituted methylene group, substituted or unsubstituted amino group, oxygen atom or sulfur atom to form a ring,

OG Complex Work Unit Chemistry
wherein, in the formula (2a),
X represents a sulfur atom;
A1 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a divalent group of a substituted or unsubstituted fused polycyclic aromatic ring, or a single bond;
Ar7 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group;
R7 and R8 may be the same or different from each other, and represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a cycloalkyl group having 5 to 10 carbon atoms, which may have a substituent group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group, and a fused polycyclic aromatic group,
wherein R7 and R8 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring; and R7 and R8 may be bonded to the substituted benzene ring to form a ring;
R9 to R12 may be the same or different from each other, represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent;
R13 and R14 may be the same or different from each other, and are a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent,

OG Complex Work Unit Chemistry
wherein, in the formula (3a-2),
X represents a sulfur atom;
A2 represents a bivalent group of a substituted or unsubstituted aromatic hydrocarbon, a bivalent group of a substituted or unsubstituted aromatic heterocyclic ring, a bivalent group of a substituted or unsubstituted fused polycyclic aromatic ring, or a single bond;
Ar8 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group;
R17 and R18 may be the same or different from each other, and represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, which may have a substituent group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group, and a fused polycyclic aromatic group,
wherein R17 and R18 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring; and R15 to R18 may be bonded to the substituted benzene ring to form a ring, via a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or a linking group; and
R19 to R22 may be the same or different from each other, represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent.