Light emitting device

Patent metadata

Field	Value
Publication number	US-12454643-B2
Application number	US-202117519492-A
Country	US
Kind code	B2
Filing date	Nov 4, 2021
Priority date	Nov 4, 2020
Publication date	Oct 28, 2025
Grant date	Oct 28, 2025

Abstract

A light emitting device includes a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, and the emission layer may include a condensed cyclic compound represented by Formula 1 below, thereby exhibiting high luminous efficiency and improved service life characteristics.

First claim

What is claimed is:

1. A light emitting device comprising:
a first electrode;
a second electrode on the first electrode; and
an emission layer between the first electrode and the second electrode and comprising a condensed cyclic compound represented by Formula 1,
wherein each of the first electrode and the second electrode independently comprises Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, W, In, Sn, Zn, a compound of two or more thereof, a mixture of two or more thereof, or an oxide thereof:

wherein, in Formula 1,
X 1 to X 4 are each independently, O, S, Se, CR 6 R 7 , or NR 8 ,
a substituent represented by Formula 2 is connected to adjacent two groups selected from among W 1 , W 2 , and W 3 , the adjacent two groups selected from among W 1 , W 2 , and W 3 are each a carbon atom, and a remaining group thereof is CR 1 ,
R 1 to R 8 are each independently a hydrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or a substituted or unsubstituted aliphatic heterocyclic group having 2 to 30 ring-forming carbon atoms, and/or are bonded to an adjacent group to form a ring,
n is an integer of 0 to 2,
o is an integer of 0 to 3, and
p and q are each independently an integer of 0 to 4,

and
wherein, in Formula 2,
Y 1 is O, S, Se, CR 1a R 2a , or NR 3a ,
Ar 1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 30 ring-forming carbon atoms,
R 1a , R 2a , and R 3a are each independently a hydrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or are bonded to an adjacent group to form a ring, and
—* is a position connected to the adjacent two groups selected from among W 1 to W 3 in Formula 1,
wherein when o is 2 or 3, and two adjacent R 3 groups are bonded to form a heteroaryl group, then the condensed cyclic compound represented by Formula 1 is represented by Formula 5:

wherein, in Formula 5,
Ar 2 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 30 ring-forming carbon atoms,
Y 11 is the same as Y 1 of Formula 1, and Ar 11 is the same as Ar 1 of Formula 1
Y 2 is O, S, Se, CR 12 R 13 , or NR 14 ,
R 12 to R 14 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or is bonded to an adjacent group to form a ring, and
X 1 to X 4 , R 1 to R 5 , and n, p, and q are the same as defined in connection with Formula 1,
and
wherein,
in Formula 5, when X 1 to X 4 are each independently O, S, Se, or NR 8 , Ar 11 and Ar 2 are each a benzene ring, and Y 11 is NR 3a , then Y 2 is O, S, Se, or CR 12 R 13 , and
in Formula 5, when X 1 to X 4 are each independently O, S, Se, or NR 8 , Ar 11 and Ar 2 are each a benzene ring, and Y 2 is NR 14 , then Y 11 is O, S, Se, or CR 1a R 2a .

2. The light emitting device of claim 1 , wherein the condensed cyclic compound represented by Formula 1 is represented by Formula 3a or Formula 3b:

and
wherein, in Formula 3a and Formula 3b,
Y 11 and Y 12 are each independently O, S, Se, CR 1b R 2b , or NR 3b ,
Ar 11 and Ar 12 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 30 ring-forming carbon atoms,
R 1b to R 3b are each independently a hydrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or are bonded to an adjacent group to form a ring, and
X 1 to X 4 , R 1 to R 5 , and n to q are the same as defined in connection with Formula 1 and Formula 2.

3. The light emitting device of claim 2 , wherein the condensed cyclic compound represented by Formula 1 is represented by Formula 4a or Formula 4b:

and
wherein, in Formula 4a and Formula 4b,
R y11 and R y12 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or are bonded to an adjacent group to form a ring,
a11 and a12 are each independently an integer of 0 to 4, and
X 1 to X 4 , Y 11 , Y 12 , R 1 to R 5 , and n to q are the same as defined in connection with Formula 1, Formula 2, Formula 3a, and Formula 3b.

4. The light emitting device of claim 2 , wherein the condensed cyclic compound represented by Formula 1 is represented by Formula 5.

5. The light emitting device of claim 4 , wherein Ar 2 is an unsubstituted benzene ring.

6. The light emitting device of claim 2 , wherein the condensed cyclic compound represented by Formula 1 is represented by Formula 6a or Formula 6b:

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Taeil
• Oh Chanseok
• Pak Sun Young
• Park Junha
• Baek Jang Yeol
• Sunwoo Kyoung
• Sim Mun-Ki
• Jung Minjung

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K85/658

  Organoboranes · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title