Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12029115-B2
Application number	US-201917251344-A
Country	US
Kind code	B2
Filing date	Sep 3, 2019
Priority date	Sep 3, 2018
Publication date	Jul 2, 2024
Grant date	Jul 2, 2024

Abstract

Provided is an organic light emitting device including a first electrode; a second electrode opposite to the first electrode; and a first organic material layer and a second organic material layer provided between the first electrode and the second electrode, wherein the first organic material layer includes a compound of Chemical Formula 1:

wherein:
at least one of Xa to Xc is N, and the rest are CR; and Ar2 to Ar4 are each independently a substituted or unsubstituted aryl or heterocyclic group, and

the second organic material layer includes a compound of

wherein:
HAr is a substituted or unsubstituted heterocyclic group including at least one or more Ns;
L1 and L2 are each independently a direct bond or a substituted or unsubstituted arylene or divalent heterocyclic group; and
Ar1 is a direct bond, —O—, or a substituted or unsubstituted arylene or divalent heterocyclic group.

First claim

The invention claimed is:

1. An organic light emitting device comprising:
a first electrode;
a second electrode provided opposite to the first electrode; and
a first organic material layer and a second organic material layer provided between the first electrode and the second electrode,
wherein the first organic material layer is a hole blocking layer or an electron control layer and includes a compound of the following Chemical Formula 1,
the second organic material layer includes a compound of the following Chemical Formula 2, and
a dipole moment value of the second organic material layer is larger than a dipole moment value of the first organic material layer:

wherein in Chemical Formula 1:
at least one of Xa to Xc is N, and the rest are CR;
R is hydrogen, deuterium, a cyano group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
Ar2 to Ar4 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;

wherein in Chemical Formula 2:
HAr is a substituted or unsubstituted heterocyclic group including one or more Ns;
L1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group;
Ar1 is a direct bond, —O—, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group;
a to c are each an integer of 1 to 3; and
when a to c are each 2 or greater, the structures in the two or more parentheses are the same as or different from each other.

2. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is the following Chemical Formula 101:

wherein in Chemical Formula 101:
Ar2 to Ar4 have the same definitions as in Chemical Formula 1.

3. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is any one of the following Chemical Formulae 1-1 to 1-3:

wherein in Chemical Formulae 1-1 to 1-3:
Xa to Xc, Ar2 and Ar3 have the same definitions as in Chemical Formula 1;
L is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylylene, or substituted or unsubstituted terphenylene;
R3, R4, R11, R12, R21 and R22 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylphosphine group, or a substituted or unsubstituted phosphine oxide group, or bond to adjacent groups to form a substituted or unsubstituted ring;
X1 and X2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted arylphosphine group, or a substituted or unsubstituted phosphine oxide group, or bond to adjacent groups to form a substituted or unsubstituted ring;
r11 and r12 are the same as or different from each other, and each independently is an integer of 0 to 5;
r21 and r22 are the same as or different from each other, and each independently is an integer of 0 to 4;
m is an integer of 1 to 3;
d is an integer of 1 to 3;
e is an integer of 1 to 4; and
when r11, r12, r21, r22, m, d and e are each 2 or greater, structures in the parentheses are the same as or different from each other.

4. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is any one of the following Chemical Formulae 1-4 to 1-6:

wherein in Chemical Formulae 1-4 to 1-6:
Ar2 and Ar3 have the same definitions as in Chemical Formula 1;
L is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylylene, or substituted or unsubstituted terphenylene;
R3, R4, R11, R12, R21 and R22 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a subst

Assignees

• Lg Chemical Ltd

Inventors

• Heo Dong Uk
• Hong Sung Kil
• Huh Jungoh
• Han Miyeon
• Lee Jae Tak
• Yang Junghoon
• Yun Heekyung

Classifications

• H10K50/10

  OLEDs or polymer light-emitting diodes [PLED] · CPC title

• H10K85/654 Primary

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

• C07D251/24 Primary

  to three ring carbon atoms · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/18

  Carrier blocking layers · CPC title