Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-2024206311-A1
Application number	US-202318488148-A
Country	US
Kind code	A1
Filing date	Oct 17, 2023
Priority date	Oct 20, 2022
Publication date	Jun 20, 2024
Grant date	—

Abstract

The present disclosure relates to organic electroluminescent devices. The organic electroluminescent device according to the present disclosure exhibits improved lifespan characteristics and progressive driving voltage by including at least one deuterated compound(s).

First claim

1 . An organic electroluminescent device comprises a plurality of light-emitting units positioned between a first electrode and a second electrode; and at least one charge generation layer positioned between the adjacent light-emitting units, wherein the light-emitting units comprise at least one light-emitting layer, and at least one of the light-emitting layer and the charge generation layer comprises a deuterated compound.

2 . The organic electroluminescent device of claim 1 , wherein the deuterium substitution rate of the deuterated compound is 30% to 100%.

3 . The organic electroluminescent device of claim 1 , wherein the deuterium substitution rate of the deuterated compound is 50% to 100%.

4 . The organic electroluminescent device of claim 1 , wherein the light-emitting layer includes a compound represented by the following Formula 1-1.

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 or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
R 1 to R 6 each independently represent, hydrogen, deuterium, halogen, 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 (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, 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 fused ring of (C3-C30) aliphatic ring and an (C6-C30) aromatic ring, 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;
a and b each independently represent, an integer of 1 or 2;
when a and b are 2 or more, each of L 1 and L 2 may be the same or different.

5 . The organic electroluminescent device of claim 1 , wherein the light-emitting layer includes two or more of compounds represented by the following formulas 1-2 to 1-4.

wherein,
Ar represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
X 1 to X 8 each independently represent, hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, 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, —NX 11 X 12 or —SiX 13 X 14 X 15 ; or the adjacent at least two of X 1 to X 6 may be linked to each other to form a ring(s);
X 11 to X 15 each independently represent, hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, 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, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to the adjacent substituents to form a ring(s):
HAr-(L 1 -Ar 2 ) d   (1-3)

wherein,
HAr represents a substituted or unsubstituted, nitrogen-containing (3- to 20-membered)heteroaryl;
L 2 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;
Ar 2 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (C3-C30)heteroaryl; and
d is an integer of 1 to 3, when d is 2 or more, each of (L 2 -Ar 2 ) may be the same or different;

wherein,
Ar 3 to Ar 5 each independently represent, hydrogen, deuterium, halogen, 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, or —N(Ar 11 )(Ar 12 );
Ar 11 and Ar 12 each independently represent, 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;
L 3 to L 5 each independently represent, 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;
provided that the cases where all of L 3 to L 5 are a single bond, while all of Ar 3 to Ar 5 are hydrogen are excluded.

6 . The organic electroluminescent device according to claim 5 , wherein the compound represented by Formula 1-2 is represented by following Formula 1-2-1 or 1-2-2.

wherein,
X 1 to X 8 and L 1 are as defined in claim 5 ;
Ar and Ar′ each independently represent, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl;
L 1 ′ is the same as the definition of L 1 in claim 5 ;
X 9 to X 18 are the same as the definition of X 1 to X 8 in claim 5 ; and
one of X 1 to X 8 and one of X 9 to X 16 are linked to each other to form a single bond;

wherein,
X 1 to X 8 and L 1 are as defined in claim 5 ;
L 7 and L 8 are the same as the definition of L 1 in claim 5 ;
Ar 7 and Ar 8 each independently represent, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (C3-

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Choi Eun-Joung
• Kim Hae-Yeon
• Kim Jin-Man
• Kim Chi-Sik
• Lee Soo-Yong
• Park So-Mi
• Jeon Jeong-Hwan
• Lee Dong-Hyung
• Rathwell Dominea
• Doh Yoo-Jin
• Seo Mi-Ran

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K85/6572 Primary

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

• H10K85/6576

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