Plurality of host materials and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-11856850-B2
Application number	US-201816640082-A
Country	US
Kind code	B2
Filing date	Sep 21, 2018
Priority date	Sep 22, 2017
Publication date	Dec 26, 2023
Grant date	Dec 26, 2023

Abstract

The present disclosure relates to a plurality of host materials and organic electroluminescent devices comprising the same. The present disclosure may provide a plurality of host materials having a composition favorable to thermal denaturation due to a low deposition temperature, while improving hole properties and electronic properties of HOMO and LUMO, by comprising separate compounds represented by formulas 1 and 2 into a light-emitting layer. By comprising the plurality of host materials of the present disclosure, it is possible to provide an organic electroluminescent device having a lower driving voltage, higher luminous efficiency and/or longer lifetime.

First claim

The invention claimed is:

1. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one layer of the light-emitting layer comprises a plurality of host materials,
wherein
the plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises a compound represented by the following formula 1:

wherein
L 1 and L 2 , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
Ar 1 and Ar 2 , each independently, represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, an amino, 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;
A represents a naphthalene ring;
B represents a benzene ring,
R 1 to R 3 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, 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 each of R 1 to R 3 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic ring;
a represents an integer of 1 to 6;
b represents 1 or 2;
c represents an integer of 1 to 4; and
where if a to c, each independently, are an integer of 2 or more, each of R 1 to R 3 may be the same or different; and
the second host material comprises a compound represented by the following formula 2:
HAr-(L 3 -Ar 3 ) d   (2)

wherein
HAr represents a substituted or unsubstituted triazine, a substituted or unsubstituted pyrimidine, or a substituted or unsubstituted pyridine;
L 3 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
Ar 3 represents a substituted or unsubstituted (C6-C30)aryl; and
d represents an integer of 1 to 3, where if d is an integer of 2 or more, each (L 3 -Ar 3 ) may be the same or different.

2. The organic electroluminescent device according to claim 1 , wherein the compound represented by formula 1 is represented by the following formula 3:

wherein, L 1 , L 2 , Ar 1 , Ar 2 , R 1 to R 3 , and a to c are as defined in claim 1 .

3. The organic electroluminescent device according to claim 1 , wherein the compound represented by formula 2 is represented by at least one of the following formula 5:

wherein
X 1 to X 6 , each independently, represent CR 4 or N, with the proviso that at least one of X 1 to X 4 represent N;
R 4 represents hydrogen, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C2-C30)alkenyl, or a substituted or unsubstituted (C1-C30)alkyl; or two adjacent R 4 's may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic ring; and
L 3 , Ar 3 and d are as defined in claim 1 .

4. The organic electroluminescent device according to claim 1 , wherein the substituents of the substituted aryl(ene), the substituted heteroaryl(ene), the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, the substituted alkylarylamino, the substituted alkyl, the substituted alkenyl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, or the substituted mono- or polycyclic ring in L 1 to L 3 , Ar 1 to Ar 3 , HAr, and R 1 to R 3 , 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 (5- to 30-membered)heteroaryl, a (C6-C30)aryl, 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.

5. The organic electroluminescent device according to claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of the following compounds:

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Kim Bitnari
• Lee Su-Hyun
• Jung So-Young
• Park Hyo-Soon
• Han Tae-Jun
• Cho Young-Jun
• Cho Sang-Hee

Classifications

• C09K2211/1018

  Heterocyclic compounds · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6572 Primary

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

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title