Condensed cyclic compound and organic light emitting device comprising same

Patent metadata

Field	Value
Publication number	US-12016243-B2
Application number	US-201917271762-A
Country	US
Kind code	B2
Filing date	Oct 2, 2019
Priority date	Dec 14, 2018
Publication date	Jun 18, 2024
Grant date	Jun 18, 2024

Abstract

Provided is a compound of Chemical Formula 1:wherein:X is O or S;one or more of R9 to R16 are linked to * of the following Chemical Formula 2; andR1 to R8, and the rest of R9 to R16 not linked to Chemical Formula 2, are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, or a substituted or unsubstituted: silyl group, boron group, alkyl group, alkoxy group, aryloxy group, cycloalkyl group, aryl group or heterocyclic group, or bond to adjacent groups to form a substituted or unsubstituted benzene ring;and an organic light emitting device including the same.

First claim

The invention claimed is:

1. An organic light emitting device, comprising:
a first electrode;
a second electrode; and
one or more organic material layers provided between the first electrode and the second electrode,
wherein at least one of the one or more organic material layers includes a hole injection layer, a hole transfer layer, or a layer carrying out hole transfer and hole injection at the same time, and the hole injection layer, the hole transfer layer, or the layer carrying out hole transfer and hole injection at the same time includes a compound of Chemical Formula 1:

wherein, in Chemical Formula 1:
X is O or S;
one or more of R9 to R16 are linked to * of the following Chemical Formula 2; and
R1 to R8, and the rest of R9 to R16 not linked to Chemical Formula 2, are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;

wherein in Chemical Formula 2:
A1 to A3 are the same as or different from each other and each independently is N or CR, and one or more of Al to A3 are N;
L1 and L2 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group;
L3 is a direct bond, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted naphthylene group;
one or more of Ar1 and Ar2 are a substituted or unsubstituted dicyclic or higher condensed aryl group, and the rest are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;
Rs are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or greater, two or more substituents in the parentheses are the same as or different from each other.

2. An organic light emitting device, comprising:
a first electrode;
a second electrode; and
one or more organic material layers provided between the first electrode and the second electrode,
wherein the one or more organic material layers include one or more light emitting layers, at least one of the one or more light emitting layers includes a host and a dopant, and the dopant is a blue fluorescent dopant having a maximum light emission wavelength of 400 nm to 520 nm, and
wherein one or more layers of the organic material layers includes a compound of Chemical Formula 1:

wherein, in Chemical Formula 1:
X is O or S;
one or more of R9 to R16 are linked to * of the following Chemical Formula 2; and
R1 to R8, and the rest of R9 to R16 not linked to Chemical Formula 2, are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;

wherein in Chemical Formula 2:
A1 to A3 are the same as or different from each other and each independently is N or CR, and one or more of Al to A3 are N;
L1 and L2 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group;
L3 is a direct bond, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted naphthylene group;
one or more of Ar1 and Ar2 are a substituted or unsubstituted dicyclic or higher condensed aryl group, and the rest are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;
Rs are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or greater, two or more substituents in the parentheses are the same as or different from each other.

3. The organic light emitting device of claim 2 , wherein the one or more organic material layers include two or more light emitting layers.

4. The organic light emitting device of claim 2 , wherein the one or more organic material layers include:
a first stack including one or more light emitting layers; and
a second stack including one or more light emitting layers; and
one or more charge generating layers between the first stack and the second stack,
wherein at least one of the first stack or the second stack includes the light emitting layer including the host and the blue fluorescent dopant having a maximum light emission wavelength of 400 nm to 520 nm.

5. The organic light emitting device of claim 2 , wherein the one or more organic material layers include:
a first stack including one or more light emitting layers;
a second stack including one or more light emitting layers;
a third stack including one or more light emitting layers; and
one or more charge generating layers between each of the first stack and the second stack, and the second stack and the third stack,
wherein at least one of the first stack, the second stack, or the third stack includes the light emitting layer including the host and the blue fluorescent dopant having a maximum light emission wavelength of 400 nm to 520 nm.

6. The organic light emitting device of claim 2 , wherein two or more of A1 to A3 are N, and the rest is CR, and R has the same definition as in Chemical Formula 2.

7. The organic light emitting device of claim 2 , wherein one or more of Ar1 and Ar2 are a substituted or unsubstituted spiro

Assignees

• Lg Chemical Ltd

Inventors

• Huh Jungoh
• Hong Sung Kil
• Lee Sangbin

Classifications

• H10K85/6574 Primary

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/131

  with spacer layers between the electroluminescent layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title