Organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-2023284526-A1
Application number	US-202118012379-A
Country	US
Kind code	A1
Filing date	Jun 29, 2021
Priority date	Jun 30, 2020
Publication date	Sep 7, 2023
Grant date	—

Abstract

To provide an organic electroluminescent device having long lifetime characteristics while having a low driving voltage and high power efficiency. The organic electroluminescent device includes one or more light-emitting layers between an anode and a cathode opposed to each other, wherein at least one of the light-emitting layers contains a host material including a first host material, a second host material and a third host material, and a light-emitting dopant material. A LUMO energy of the first host material is −1.95 eV or less, and LM2≥LM3≥LM1 is satisfied under the assumption that LUMO energies of the first host material, the second host material and the third host material are LM1, LM2 and LM3, respectively. A suitable first host material is an indolocarbazole compound represented by general formula (1), a suitable second host material is, for example, a biscarbazole compound represented by general formula (2), and a suitable third host material is an indolocarbazole compound represented by general formula (5).

First claim

1 - 19 . (canceled)

20 . An organic electroluminescent device comprising one or more light-emitting layers between an anode and a cathode opposed to each other, wherein at least one of the light-emitting layers contains a host material comprising a first host material, a second host material and a third host material, and a light-emitting dopant material, a LUMO energy of the first host material is −1.95 eV or less, a LUMO energy of the second host material is −1.54 eV or more, and LM2≥LM3≥LM1 is satisfied under the assumption that LUMO energies of the first host material, the second host material and the third host material are LM1, LM2 and LM3, respectively.

21 . The organic electroluminescent device according to claim 20 , wherein the LUMO energy of the third host material is −1.94 to −1.77 eV.

22 . The organic electroluminescent device according to claim 20 , wherein triplet excitation (T 1 ) energies of the first host material, the second host material and the third host material are each 2.55 eV or more.

23 . The organic electroluminescent device according to claim 20 , which is an organic electroluminescent device comprising one or more light-emitting layers between an anode and a cathode opposed to each other, wherein at least one of the light-emitting layers contains a first host material, a second host material and a third host material, and a light-emitting dopant material, and at least three materials contained in the light-emitting layers are vapor deposited from one vapor deposition source.

24 . The organic electroluminescent device according to claim 23 , wherein the first host material, the second host material and the third host material are vapor deposited from one vapor deposition source.

25 . The organic electroluminescent device according to claim 20 , wherein the light-emitting dopant material is a material emitting fluorescence including thermally activated delayed fluorescence material.

26 . The organic electroluminescent device according to claim 20 , wherein the light-emitting dopant material is a phosphorescence-emitting material.

27 . The organic electroluminescent device according to claim 20 , wherein the first host material is a compound represented by the following general formula (1):

wherein a ring A is a heterocycle represented by formula (1a) and the ring A is fused to an adjacent ring at any position,
R 1 independently represents 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 17 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two to five of these aromatic rings are linked to each other,
a, c and d each independently represent an integer of 0 to 4, and b represents an integer of 0 to 2,
L 1 and L 11 independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, and at least one thereof represents the aromatic heterocyclic group, and
Ar 1 and Ar 11 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two to seven of these aromatic rings am linked to each other.

28 . The organic electroluminescent device according to claim 27 , wherein at least one of L 1 and L 11 is a substituted or unsubstituted nitrogen-containing 6-membered ring group, or a substituted or unsubstituted ring-fused aromatic heterocyclic group containing a nitrogen-containing 6-membered ring.

29 . The organic electroluminescent device according to claim 27 , wherein the general formula (1) is the following formula (11):

wherein R 1 , ring A, Ar 1 , a, and b are as defined for the general formula (1).

30 . The organic electroluminescent device according to claim 29 , wherein the formula (11) is a compound represented by the following formula (12) or formula (13):

wherein R 1 , ring A, Ar 1 , a and b are as defined for the general formula (1),
Y represents O, S, NAr 4 , or CAr 15 Ar 16 ,
Ar 13 , Ar 14 , Ar 15 , and Ar 16 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 17 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two to five of these aromatic rings are linked to each other,
m represents an integer of 0 to 4, n represents an integer of 0 to 3, and l represents an integer of 0 to 4,
L 12 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms,
L 13 represents a nitrogen-containing 6-membered ring group, and
Ar 12 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two to five of these aromatic rings are linked to each other.

31 . The organic electroluminescent device according to claim 20 , wherein the second host material is a compound represented by the following general formula (2), general formula (3), or general formula (4):

wherein Ar 21 and Ar 22 independently represent hydrogen, deuterium, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two of the aromatic rings are linked to each other;
and L 21 and L 22 independently represent a direct bond or a phenylene group;

wherein a ring B is a heterocycle represented by formula (3a) and the ring B is fused to an adjacent ring at any position,
R 3 independently represents 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 17 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 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 17 carbon atoms,
L 32 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms,
Ar 31 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted ca

Assignees

• Nippon Steel Chemical & Mat Co Ltd

Inventors

• Kai Takahiro
• Hayashi Kentaro
• Ogawa Junya
• Ikenaga Yuji
• TERADA Ayaka
• Yoshida Kazunari
• Kitahara Ikumi
• IZUMI Haruka
• Noguchi Katsuhide
• Kawada Atsushi

Classifications

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• H10K71/16

  using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/6576

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