Luminescence device and amine compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-12178121-B2
Application number	US-202117445815-A
Country	US
Kind code	B2
Filing date	Aug 24, 2021
Priority date	Oct 21, 2020
Publication date	Dec 24, 2024
Grant date	Dec 24, 2024

Abstract

An organic electroluminescence device includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, an electron transport region on the emission layer, and a second electrode on the electron transport region. The hole transport region may include an amine compound represented by Formula 1, thereby exhibiting high luminous efficiency:

First claim

What is claimed is:

1. A luminescence device comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the hole transport region comprises an amine compound represented by Formula 1:

wherein, in Formula 1,
R 1 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 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,
at least one among R 1 to R 10 is represented by Formula 2, and
ring A and ring B are each independently represented by Formula 3 or Formula 4, and are represented by different formulae:

wherein, in Formula 2,
L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms,
n is an integer of 0 to 3, and
Ar1 and Ar2 are each independently 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
wherein, in Formula 3 and Formula 4,
R 11 and R 12 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 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,
a is an integer of 0 to 4, and
b is an integer of 0 to 6.

2. The luminescence device of claim 1 , wherein the hole transport region comprises:
a hole injection layer on the first electrode; and
a hole transport layer on the hole injection layer, and
wherein the hole transport layer or the hole injection layer comprises the amine compound represented by Formula 1.

3. The luminescence device of claim 2 , wherein the hole transport region further comprises an electron blocking layer on the hole transport layer.

4. The luminescence device of claim 1 , wherein Formula 1 is represented by Formula 5 or Formula 6:

and
wherein, in Formula 5 and Formula 6,
R 1 to R 12 , a, and b are the same as defined in Formula 1, Formula 3, and Formula 4.

5. The luminescence device of claim 4 , wherein Formula 5 is represented by Formula 7-1:

and
wherein, in Formula 7-1,
R x , and R 5 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 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,
c is an integer of 0 to 3,
L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms,
n is an integer of 0 to 3,
Ar1 and Ar2 are each independently 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
R 11 , R 12 , a, and b are the same as defined in Formula 5.

6. The luminescence device of claim 5 , wherein Formula 7-1 is represented by Formula 8-1:

and
wherein, in Formula 8-1,
R x , R 5 to R 12 , L, Ar1, Ar2, a to c, and n are the same as defined in Formula 7-1.

7. The luminescence device of claim 4 , wherein Formula 5 is represented by Formula 7-2 or Formula 7-3:

and
wherein, in Formulae 7-2 and 7-3,
R y , and R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 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,
d is an integer of 0 to 5,
L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms,
n is an integer of 0 to 3,
Ar1 and Ar2 are each independently 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
R 11 , R 12 , a, and b are the same as defined in Formula 5.

8. The luminescence device of claim 7 , wherein Formula 7-2 is represented by Formula 8-2:

and
wherein, in Formula 8-2,
R y , R 1 to R 4 , R 11 , R 12 , L, Ar1, Ar2, a, b, d, and n are the same as defined in Formula 7-2.

9. The luminescence device of claim 4 , wherein Formula 6 is represented by Formula 9-1:

and
wherein, in Formula 9-1,
R x , and R 5 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 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,
c is an integer of 0 to 3,
L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms,
n is an integer of 0 to 3,
Ar1 and Ar2 are each independently 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
R 11 , R 12 , a, and b are the same as defined in Formula 6.

10. The luminescence device of claim 9 , wherein Formula 9-1 is represented by Formula 10-1:

and
wherein, in Formula 10-1,
R x , R 5 to R 12 , L, Ar1, Ar2, a to c, and n are the same as defined in Formula 9-1.

11. The luminescence device of claim 4 , wherein Formula 6 is represented by Formula 9-2 or Formula 9-3:

and
where

Assignees

• Samsung Display Co Ltd

Inventors

• Pak Hankyu
• Jeong Eunjae
• Han Sanghyun
• Kim Dongjun
• Kim Minji
• Jo Sohee

Classifications

• C07D333/76

  Dibenzothiophenes · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D209/88

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system · CPC title

• C07C211/61 Primary

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C07C2603/94

  containing "free" spiro atoms · CPC title