Compound and organic electronic element comprising same

Patent metadata

Field	Value
Publication number	US-11974497-B2
Application number	US-201716308231-A
Country	US
Kind code	B2
Filing date	Jul 3, 2017
Priority date	Jul 1, 2016
Publication date	Apr 30, 2024
Grant date	Apr 30, 2024

Abstract

A compound of Chemical Formula 4 or 5:

wherein: one of X1 and X2 is a direct bond, and the other is O, S, or CY1Y2, one of X3 and X4 is a direct bond, and the other is O, S, or CY3Y4, W1 to W4 are each independently N or CRa, and one or more of W1 to W4 are N, Y1 to Y4 are the same as or different from each other, and are each independently an alkyl group having 1 to 20 carbon atoms, and the other substituents are as defined in the specification; and an organic light emitting device comprising the same. The compound can lower the driving voltage, improve the light efficiency, and enhance service life characteristics of the device due to thermal stability of the compound.

First claim

The invention claimed is:

1. A compound represented by the following Chemical Formula 4 or 5:

in Chemical Formulae 4 and 5,
any one of X1 and X2 is a direct bond, and the other is O, S, or CY1Y2,
any one of X3 and X4 is a direct bond, and the other is O, S, or CY3Y4,
W1 to W4 are the same as or different from each other, and are each independently N or CRa, and one or more of W1 to W4 are N, and
Y1 to Y4 are the same as or different from each other, and are each independently an alkyl group having 1 to 20 carbon atoms,
Ra, R14 and R23 are hydrogen,
R15 to R22 are hydrogen; or form an aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding to an adjacent group among Ra, and R14 to R23,
L101, L102, and L1 to L4 are each a direct bond,
Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted pyridyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or the moieties

of the Chemical
Formula 4 or 5 can be each independently a substituted or unsubstituted carbazole, R1 to R9 are the same as or different from each other, and are each independently hydrogen; deuterium; or an alkyl group having 1 to 20 carbon atoms,
R10 to R13 are hydrogen,
R4 and R5 are bonded to each other to form a pentagonal ring,
m and n are an integer of 0 or 1, and
at least one of m and n is an integer of 1.

2. The compound of claim 1 , wherein the compound of Chemical Formula 4 or 5 is represented by one of the following Chemical Formulae 10 to 13 and Chemical Formulae 18 to 21:

in Chemical Formulae 10 to 13 and Chemical Formulae 18 to 21,
L101, L102, L1 to L4, Ar1 to Ar4, R1 to R3, R6 to R23, m, n, X1 to X4, and W1 to W4 are the same as defined in Chemical Formulae 4 and 5.

3. The compound of claim 1 , wherein Ar1 to Ar4 are any one selected from the substituents described below:

in the structures,
R201, R203, R205, R206, and R257 to R259 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; or an alkyl group having 1 to 20 carbon atoms,
R202, R228, and R229 are the same as or different from each other, and are each independently hydrogen; or an alkyl group having 1 to 20 carbon atoms, and
a1 to a3, a5, a6, a8, a9, and b18 are each an integer of 0 or 1.

4. The compound of claim 1 , wherein the compound of Chemical Formula 4 or 5 is any one selected from the following compounds:

5. An organic electronic device comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode,
wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound of claim 1 as a dopant of the light emitting layer.

6. The organic electronic device of claim 5 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following Chemical Formula 1A:

in Chemical Formula 1A,
L103 to L106 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar5 to Ar8 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
R24s are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
p is an integer from 0 to 6, and
when p is 2 or more, substituents in the parenthesis are the same as or different from each other.

7. The organic electronic device of claim 6 , wherein Ar5 to Ar8 are the same as or different from each other, and are each independently hydrogen; or selected from the following structures:

8. The organic electronic device of claim 5 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following Chemical Formula 1B:

Assignees

• Lg Chemical Ltd

Inventors

• Koo Ki Dong
• Jeong Hyunseok
• Kim Kongkyeom
• Lee Younghee
• Lee Woochul

Classifications

• H10K50/12

  comprising dopants · CPC title

• H10K85/654

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

• H10K85/6572

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

• H10K85/40

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

• H10K85/6574

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