Plurality of host materials, organic electroluminescent compound and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-12588353-B2
Application number	US-202217825399-A
Country	US
Kind code	B2
Filing date	May 26, 2022
Priority date	Jun 3, 2021
Publication date	Mar 24, 2026
Grant date	Mar 24, 2026

Abstract

The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same. By comprising the specific combination of compounds according to the present disclosure as a plurality of host materials according to the present disclosure, it is possible to provide an organic electroluminescent device having improved driving voltage, luminous efficiency, and/or lifetime property compared to the conventional organic electroluminescent devices.

First claim

The invention claimed is:

1 . A plurality of host materials comprising a first host material comprising the compound represented by formula 1, and a second host material comprising the compound represented by formula 2:

in formula 1,
L represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C3-C30)cycloalkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-to 30-membered)heteroarylene;
Ar represents deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3-to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-to 30-membered) heteroaryl, —NR 11 R 12 , or —SiR 13 R 14 R 15 ;
R 11 to R 15 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-to 30-membered)heteroaryl; and

 is represented by the following formula 1-1 or 1-2:

in formulas 1-1 and 1-2,
X 1 to X 25 , each independently, represent —N═ or —C(R a )═;
R a , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri (C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri (C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C2-C30) alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3-to 30-membered)heteroarylamino, a substituted or unsubstituted (C1-C30)alkyl(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl (3-to 30-membered)heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl (C6-C30)arylamino, a substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl (3-to 30-membered)heteroarylamino, or the adjacent R a 's may be linked to each other to form a ring(s), and where if there is a plurality of R a , each of R a may be the same or different from each other; with the provisos that:
R a in X 5 is not linked to the adjacent R a in X 6 to form a ring(s);
R a in X 9 is not linked to the adjacent R a in X 10 to form a ring(s);
R a in X 18 is not linked to the adjacent R a in X 19 to form a ring(s); and
R a in X 22 is not linked to the adjacent R a in X 23 to form a ring(s); and

in formula 2,
X′ represents O, S, or CR 5 R 6 ;
R 1 to R 4 , each independently, represent hydrogen, deuterium, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3-to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-to 30-membered)heteroaryl, -L 3 -NR 16 R 17 , or —SiR 18 R 19 R 20 ; or may be linked to adjacent substituent(s) to form a ring(s);
wherein, at least one of R 1 to R 4 represents a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3-to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-to 30-membered)heteroaryl, -L 3 -NR 16 R 17 , or —SiR 18 R 19 R 20 ;
L 3 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-to 30-membered)heteroarylene;
R 5 and R 6 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-to 30-membered)heteroaryl, or R 5 and R 6 may be linked to each other to form a ring(s);
R 16 to R 20 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-to 30-membered)heteroaryl; and
a′ and d′, each independently, represent an integer of 1 to 4, b′ and c′, each independently, represent an integer of 1 or 2, and where if each of a′ to d′ is an integer of 2 or more, each of R 1 to each of R 4 may be the same or different from each other.

2 . The plurality of host materials according to claim 1 , wherein formula 1-1 is represented by the following formula 1-1-1:

in formula 1-1-1,
R 31 to R 33 , each independently, are the same as the definition of R a , with the provisos that:
R 31 is not linked to the adjacent R 32 to form a ring(s); and
R 32 is not linked to the adjacent R 33 to form a ring(s); and
aa represents an integer of 1 to 5, ab represents an integer of 1 to 4, ac represents an integer of 1 to 3, and where if aa, ab, and ac are an integer of 2 or more, each of R 31 , each of R 32 , and each of R 33 may be the same or different from each other.

3 . The plurality of host materials according to claim 1 , wherein formula 1-2 is represented by the following formula 1-2-1:

in formula 1-2-1,
R 41 to R 44 , each independently, are the same as the definition of R a , with the provisos that:
R 42 is not linked to the adjacent R 43 to form a ring(s); and
R 43 is not linked to the adjacent R 44 to form a ring(s); and
ba represents an integer of 1 or 2, bb and bc, each independently, represent an integer of 1 to 4, bd represents an integer of 1 to 3, and where if ba, bb, bc, and bd are an integer of 2 or more, each of R 41 , each of R 42 , each of R 43 , and each of R 44 may be the same or different from each other.

4 . The plurality of host materials according to claim 1 , in formula 2,
at least one of R 1 to R 4 is-L 2 -HAr or -L 3 -NR 16 R 17 ; L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-to 30-membered)heteroarylene; HAr represents a substituted or unsubstituted (3-to 30-membered)heteroaryl comprising at least one of N, O and S; and L 3 , R 16 , and R 17 , each independently, are as defined in claim 1 .

5 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 2 is represented by any one of the following formulas 2-1 to 2-4:

in formulas 2-1 to 2-4,
X′

Assignees

• Rohm & Haas Elect Materials Korea Ltd
• Dupont Specialty Materials Korea Ltd

Inventors

• Cho Sang-Hee
• Kim Bitnari
• Kim Young-Jae
• Jung So-Young
• Lee Mi-Ja
• Lee Su-Hyun
• Han Tae-Jun
• Kim Haeyeon

Classifications

• H10K85/00

  Organic materials used in the body or electrodes of devices covered by this subclass · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K85/6576

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

• H10K85/6574

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

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title