Organic electroluminescence device and compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-11844274-B2
Application number	US-201916721613-A
Country	US
Kind code	B2
Filing date	Dec 19, 2019
Priority date	Apr 5, 2019
Publication date	Dec 12, 2023
Grant date	Dec 12, 2023

Abstract

An organic electroluminescence device of an embodiment includes oppositely disposed first electrode and second electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one among the organic layers includes a compound represented by Formula 1 below. Improved emission efficiency and color purity properties may be shown.

First claim

What is claimed is:

1. An organic electroluminescence device, comprising:
a first electrode;
a second electrode disposed on the first electrode; and
a plurality of organic layers disposed between the first electrode and the second electrode,
wherein at least one organic layer among the organic layers comprises a compound represented by Formula 1:

wherein in Formula 1,
L 1 and L 2 are each independently a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring,
“n” is 0 or 1,
FU is a deuterium atom, a halogen atom, a cyano group, an amino group, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group of 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group of 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted alkylamine group of 1 to 10 carbon atoms, a substituted or unsubstituted arylamine group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted piperidine group,
FU and DU are different from each other, and
DU is represented by Formula 2:

wherein in Formula 2,
X is a direct linkage, O, S, or CR a R b ,
R a and R b are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring,
R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted alkylamine group of 1 to 10 carbon atoms, a substituted or unsubstituted arylamine group of 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring, and
“a” and “b” are each independently an integer of 0 to 4, and
wherein L 2 is an unsubstituted phenylene group when n is 0.

2. The organic electroluminescence device of claim 1 , wherein the organic layers comprise:
an emission layer;
a hole transport region disposed between the first electrode and the emission layer; and
an electron transport region disposed between the emission layer and the second electrode,
wherein the emission layer comprises the compound represented by Formula 1.

3. The organic electroluminescence device of claim 2 , wherein the emission layer emits delayed fluorescence.

4. The organic electroluminescence device of claim 2 , wherein the emission layer is a delayed fluorescence emission layer comprising a host and a dopant, and
the dopant comprises the compound represented by Formula 1.

5. The organic electroluminescence device of claim 2 , wherein the emission layer emits blue light.

6. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by Formula 1-1:

wherein in Formula 1-1, “n”, FU, and DU are the same as defined in Formula 1.

7. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by Formula 1-2:

wherein in Formula 1-2, “n”, FU, and DU are the same as defined in Formula 1.

8. The organic electroluminescence device of claim 1 , wherein Formula 2 is represented by any one among the following D1 to D5:

wherein in D1 to D5, R 1 , R 2 , “a” and “b” are the same as defined in Formula 2.

9. The organic electroluminescence device of claim 1 , wherein the compound represented by Formula 1 comprises at least one among compounds in the following Compound Group 1:

10. A compound represented by Formula 1:

wherein in Formula 1,
L 1 and L 2 are each independently a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring,
“n” is 0 or 1,
FU is a deuterium atom, a halogen atom, a cyano group, an amino group, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group of 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group of 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted alkylamine group of 1 to 10 carbon atoms, a substituted or unsubstituted arylamine group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted piperidine group,
FU and DU are different from each other, and
DU is represented by Formula 2:

wherein in Formula 2,
X is a direct linkage, O, S, or CR a R b ,
R a and R b are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring,
R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted alkylamine group of 1 to 10 carbon atoms, a substituted or unsubstituted arylamine group of 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring, and
“a” and “b” are each independently an integer of 0 to 4, and
wherein L 2 is an unsubstituted phenylene group when n is 0.

11. The compound of claim 10 , wherein L 1 and L 2 are the same.

12. The compound of claim 10 , wherein L 1 and L 2 are unsubstituted phenylene groups.

13. The compound of claim 10 , wherein Formula 1 is represented by Formula 1-1:

wherein in Formula 1-1, “n”, FU, and DU are the same as defined in Formula 1.

14. The compound of claim 10 , wherein Formula 1 is represented by Formula 1-2:

wherein in Formula 1-2, “n”, FU, and DU are the same as defined in Formula 1.

15. The compound of claim 10 , wherein Formula 2 is represented by any one among the following D1 to D5:

wherein in D1 to D5, R 1 , R 2 , “a” and “b” are the same as defined in Formula

Assignees

• Samsung Display Co Ltd
• Seoul Nat Univ R&Db Foundation

Inventors

• Park Sooyoung
• Kim Sehun
• Kwon Jieon
• Kim Hyojeong
• Ryoo Chihyun
• Lee Changhee
• Jeong Hyein
• Han Jongseok

Classifications

• H10K85/6572 Primary

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

• H10K85/631 Primary

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C07D219/02 Primary

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

• C07D209/86

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