Organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-2023113101-A1
Application number	US-202017785348-A
Country	US
Kind code	A1
Filing date	Dec 11, 2020
Priority date	Dec 27, 2019
Publication date	Apr 13, 2023
Grant date	—

Abstract

To provide an organic electroluminescent device having high efficiency while having a driving voltage. This organic electroluminescent device includes an anode, an organic layer and a cathode stacked on a substrate, at least one layer of the organic layer is a light-emitting layer containing a first host, a second host and a light-emitting dopant material, the first host is selected from a compound represented by the following general formula (1), and the second host is selected from a biscarbazole compound binding at a position other than the N-position, an indolocarbazole compound, or a carbazole compound in which a plurality of carbazole rings bind at the N-position. In the formula, a ring A is represented by formula (1b) or (1c), X represents NR, S, O, or CR2, and at least one Y represents N.

First claim

1 . An organic electroluminescent device comprising an anode, an organic layer and a cathode stacked on a substrate, wherein at least one layer of the organic layer is a light-emitting layer containing a first host, a second host and a light-emitting dopant material,
the first host is selected from a compound represented by the following general formula (1), and the second host is selected from a compound represented by the following general formula (2), general formula (3), or general formula (4):

wherein a ring A is represented by formula (1b) or (1c) and is fused to an adjacent ring at any position; and * represents C or CR, and two adjacent * in the formula (1b) or formula (1c) bind to * of an adjacent ring;
X represents NR 11 , S, O, or CR 12 R 13 , and R 11 , R 12 , and R 13 each independently represent an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two to five of these aromatic rings are linked to each other;
R independently represents hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two to three of these aromatic groups are linked to each other;
Y independently represents N or CR 14 , and at least one Y represents N;
R 14 represents hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two to five of these aromatic rings are linked to each other;
Ar 1 and Ar 2 are independently an aromatic heterocyclic group represented by formula (1 a);
Ar 3 independently represents hydrogen, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two to five of these aromatic rings are linked to each other;
L 1 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms;

wherein Ar 21 and Ar 22 independently represent hydrogen, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two of the aromatic hydrocarbon groups are linked to each other; and
L 21 and L 22 independently represent a phenylene group;

wherein a ring c is a heterocycle represented by formula (3a) and the ring c is fused to an adjacent ring at any position;
R 03 and R 32 independently represent hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms;
R 31 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a carbazolyl group, or a substituted or unsubstituted linked aromatic group in which two to five of these aromatic rings are linked to each other;
L 31 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms;
Ar 31 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms;
f is the number of repetitions and represents an integer of 1 to 3, g is the number of repetitions and independently represents an integer of 0 to 3, and h is the number of substitutions and represents an integer of 1 to 7;

wherein L 41 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or a linked aromatic group in which two to five of these aromatic rings are linked; R 41 each independently represents hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, provided that R 41 is not a carbazole group; x is the number of repetitions and independently represents an integer of 1 to 4, provided that at least one x is an integer of 2 to 4; y is the number of substitutions and represents an integer of 1 to 4; and when x and y are each 2 or more, a plurality of carbazolyl groups in the formula may be the same or different.

2 . The organic electroluminescent device according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following formula (5):

wherein R, Ar 1 , Ar 2 , Ar 3 , and L 1 have the same meaning as in the general formula (1); and a ring a is represented by formula (5a) and the ring a is fused to an adjacent ring at any position, X represents NR 51 , S, O, or CR 52 R 53 , and R 51 , R 52 and R 53 each independently represent an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or a linked aromatic group in which two to five of these groups are linked to each other.

3 . The organic electroluminescent device according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following formula (6):

wherein R, Ar 1 , Ar 2 , Ar 3 , and L 1 have the same meaning as in the general formula (1); and Cz represents a carbazole group represented by formula (6a) or formula (6b).

4 . The organic electroluminescent device according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by any of formulas (7) to (12):

wherein L 1 , Ar 2 , Ar 3 , R, and R 11 have the same meaning as in the general formula (1).

5 . The organic electroluminescent device according to claim 1 , wherein the compound represented by the general formula (2) is used as the second host.

6 . The organic electroluminescent device according to claim 5 , wherein the compound represented by the general formula (2) is a compound represented by the following formula (13):

Assignees

• Nippon Steel Chemical & Mat Co Ltd

Inventors

• Ogawa Junya
• Tada Masashi
• Kai Takahiro
• Yoshida Kazunari
• Kitahara Ikumi

Classifications

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/342

  comprising iridium · CPC title