Plurality of host materials and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-12389794-B2
Application number	US-201917263137-A
Country	US
Kind code	B2
Filing date	Jul 24, 2019
Priority date	Jul 25, 2018
Publication date	Aug 12, 2025
Grant date	Aug 12, 2025

Abstract

The present disclosure relates to a plurality of host materials comprising a first host material comprising a compound represented by the following formula 1, and a second host material comprising a compound represented by the following formula 2, and an organic electroluminescent device comprising the same. By comprising a specific combination of compounds as a host material, it is possible to provide an organic electroluminescent device having higher luminous efficiency and/or improved lifespan characteristics compared to conventional organic electroluminescent devices.

First claim

The invention claimed is:

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

wherein
X represents O;
R 1 to R 8 each independently represent-L 1 -HAr, hydrogen, 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 9 R 10 , or-SiR 11 R 12 R 13 ; or may be linked to an adjacent substituent to form a ring; with a proviso that at least one of R 3 to R 6 is-L 1 -HAr;
L 1 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene, where if a plurality of L 1 is present, each of L 1 may be the same or different;
HAr represents a substituted or unsubstituted nitrogen-containing (3-to 30-membered) heteroaryl, where if a plurality of HAr is present, each HAr may be the same or different;
with proviso that (1) when HAr is a substituted or unsubstituted triazine and L 1 is a substituted or unsubstituted (C6-C30) arylene, the (C6-30) arylene is selected from the group consisting of a naphthylene, a naphthylphenylene, or a phenylnaphthylene;
or (2) when HAr is a substituted triazine and L 1 is a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene, at least one of substitutions in HAr is a naphthyl, a phenylnaphthyl, or a naphthylphenyl; or
(3) when HAr is a substituted triazine and L 1 is a single bond, one of two substitutions in HAr is a naphthyl, or a naphthylphenyl and the other one of two substitutions in HAr is a (C6-C30) aryl unsubstituted or substituted with at least one of a deuterium, a (C1-C30) alkyl(s), a (3-to 30-membered) heteroaryl(s), and a di (C6-C30) arylamino(s);

wherein
L 2 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene;
Ar represents hydrogen, 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 9 R 10 , or-SiR 11 R 12 R 13 ;
or may be linked to an adjacent substituent to form a ring;

is represented by the following formula 3;

wherein
X 1 to X 12 each independently represent N or CR 14 ;
R 14 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-(C6-C30) arylamino, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or adjacent R 14 's may be linked to each other to form a ring, and where if a plurality of R 14 is present, each R 14 may be the same or different;
R 9 to R 13 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
* represents a bonding site with L 2 .

2. The plurality of host materials according to claim 1 , wherein the substituents of the substituted alkyl, the substituted alkylene, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkylene, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono-or di-alkylamino, the substituted mono-or di-arylamino, and the substituted alkylarylamino in R 1 to R 14 , L 1 , L 2 , HAr, and Ar, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30) alkyl; a halo (C1-C30) alkyl; a (C2-C30) alkenyl; a (C2-C30) alkynyl; a (C1-C30) alkoxy; a (C1-C30) alkylthio; a (C3-C30) cycloalkyl; a (C3-C30) cycloalkenyl; a (3-to 7-membered) heterocycloalkyl; a (C6-C30) aryloxy; a (C6-C30) arylthio; a (3-to 30-membered) heteroaryl unsubstituted or substituted with a (C6-C30) aryl(s); a (C6-C30) aryl unsubstituted or substituted with at least one of a (C1-C30) alkyl(s), a (3-to 30-membered) heteroaryl(s), and a di (C6-C30) arylamino(s); a tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl; a di (C1-C30) alkyl (C6-C30) arylsilyl; a (C1-C30) alkyldi (C6-C30) arylsilyl; an amino; a mono-or di-(C1-C30) alkylamino; a mono-or di-(C6-C30) arylamino; a (C1-C30) alkyl (C6-C30) arylamino; a (C1-C30) alkylcarbonyl; a (C1-C30) alkoxycarbonyl; a (C6-C30) arylcarbonyl; a di (C6-C30) arylboronyl; a di (C1-C30) alkylboronyl; a (C1-C30) alkyl (C6-C30) arylboronyl; a (C6-C30) aryl (C1-C30) alkyl; and a (C1-C30) alkyl (C6-C30) aryl.

3. The plurality of host materials according to claim 1 , wherein formula 1 is represented by at least one of the following formulas 1-3 to 1-4:

wherein
R 1 to R 8 , X, L 1 , and HAr are as defined in claim 1 .

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

wherein
R 31 to R 33 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-(C6-C30) arylamino, or a substituted or unsubstituted

Assignees

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

Inventors

• Lee Su-Hyun
• Kim Bitnari
• Shin Hyo-Nim
• Yang Jeong-Eun
• Cho Sang-Hee
• Han Tae-Jun
• Park Hyo-Soon
• Jung So-Young

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title