Organic electroluminescent device comprising an electron buffer layer and an electron transport layer

Patent metadata

Field	Value
Publication number	US-11930704-B2
Application number	US-202218062715-A
Country	US
Kind code	B2
Filing date	Dec 7, 2022
Priority date	Sep 13, 2016
Publication date	Mar 12, 2024
Grant date	Mar 12, 2024

Abstract

The present disclosure relates to an organic electroluminescent device. The organic electroluminescent device of the present disclosure comprises a specific combination of an electron buffer material and an electron transport material which can provide high efficiency and/or long lifespan.

First claim

The invention claimed is:

1. An organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and an electron transport layer and an electron buffer layer between the light-emitting layer and the second electrode, wherein the electron buffer layer comprises a compound represented by any one of the following formulae 5 to 8, and the electron transport layer comprises a compound represented by the following formula 2:

wherein
Y 1 represents N or CR 13 ;
Ar 1 and Ar 2 , Ar 5 to Ar 9 , and Ar 13 to A 19 , each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C50)aryl, a substituted or unsubstituted (3- to 50-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 may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic, aromatic, or a combination of alicyclic and aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
L represents a single bond, a substituted or unsubstituted (C6-C50)arylene, or a substituted or unsubstituted (5- to 50-membered)heteroarylene; and
X represents CRaRb, NRc, O, or S, wherein Ra, Rb, and Rc are each independently identical to the definition of Ar 1 ;
K represents CRd or N, wherein Rd is identical to the definition of Ar 1 ;
M represents O or S;
A 1 represents —N═, —NR 7 —, —O—, or —S—;
B 1 represents —N═, —NR 8 —, —O—, or —S—, with a proviso that B 1 is —NR 8 —, —O—, or —S— when A 1 is —N═, and B 1 is —N═, —O—, or —S— when A 1 is —NR 7 —;
R 1 represents a substituted or unsubstituted (C6-C30)aryl wherein the substituents of the (C6-30)aryl are at least one selected from the group consisting of deuterium, a (C1-30)alkyl, a (C6-30)aryl(C1-C30)alkyl and a (C1-C30)alkyl(C6-30)aryl;
R 2 to R 4 , R 7 , and R 8 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 may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic, aromatic, or a combination of alicyclic and aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
h, i, and p each independently represent an integer of 1 to 4, q and q each independently represent an integer of 1 to 3, and n, o, r, and s each independently represent 1 or 2;
a represents 1, b and c each independently represent 1 or 2, and d represents an integer of 1 to 4; and
the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.

2. The organic electroluminescent device according to claim 1 , wherein the compound represented by any one of formulae 5 to 8 is selected from the group consisting of:

3. The organic electroluminescent device according to claim 1 , wherein the compound represented by formula 2 is selected from the group consisting of:

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Ahn Hee-Choon
• Moon Doo-Hyeon
• Cho Sang-Hee

Classifications

• H10K85/6572 Primary

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

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K85/633

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title