Organic electroluminescence device and fused polycyclic compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-11489124-B2
Application number	US-202016882900-A
Country	US
Kind code	B2
Filing date	May 26, 2020
Priority date	Jul 8, 2019
Publication date	Nov 1, 2022
Grant date	Nov 1, 2022

Abstract

An organic electroluminescence device of the present embodiments 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 plurality of organic layers includes a fused polycyclic compound represented by Formula 1 below, thereby showing improved emission efficiency:

First claim

What is claimed is:

1. An organic electroluminescence device, comprising:
a first electrode;
a second electrode facing the first electrode; and
a plurality of organic layers between the first electrode and the second electrode,
wherein the first electrode and the second electrode are each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, and Zn, or a compound of two or more selected from them, a mixture of two or more selected from them, or oxides of one or more selected from them, and
wherein at least one organic layer among the plurality of organic layers comprises a fused polycyclic compound represented by Formula 1:

wherein, in Formula 1,
M is B, Al, Ga, or In,
X 1 and X 2 are each independently NR 1 , O, S, P(═O)R 2 , or P(═S)R 3 ,
R 1 to R 3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R 1 to R 3 are optionally combined with an adjacent group to form a ring,
Cy 1 to Cy 3 are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle, and any of Cy 1 to Cy 3 are optionally combined with an adjacent group to form a ring, and
at least one among Cy 1 to Cy 3 is substituted with a substituent represented by Formula 2:

wherein, in Formula 2,
R 4 and R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R 4 and R 5 are optionally combined with an adjacent group to form a ring,
n 1 and n 2 are each independently an integer of 0 to 4,
at least one among R 4 and R 5 is a substituted or unsubstituted amine group, or a substituted or unsubstituted carbazole group,
if R 4 is the substituted or unsubstituted amine group, or the substituted or unsubstituted carbazole group, n 1 is an integer of 1 to 4,
if R 5 is the substituted or unsubstituted amine group, or the substituted or unsubstituted carbazole group, n 2 is an integer of 1 to 4,
Y is a direct linkage, and
a is 0 or 1.

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

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

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

5. The organic electroluminescence device of claim 2 , wherein
the emission layer comprises:
a first compound having a first lowest triplet excitation energy level;
a second compound having a second lowest triplet excitation energy level which is lower than the first lowest triplet excitation energy level; and
a third compound having a third lowest triplet excitation energy level which is lower than the second lowest triplet excitation energy level, and
the second compound comprises the fused polycyclic compound represented by Formula 1.

6. The organic electroluminescence device of claim 5 , wherein
the second compound is a delayed fluorescence material, and
the third compound is a phosphorescence material or a fluorescence material.

7. The organic electroluminescence device of claim 1 , wherein
the fused polycyclic compound represented by Formula 1 is represented by Formula 3:

wherein, in Formula 3,
R 11 to R 21 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R 11 to R 21 are optionally combined with an adjacent group to form a ring,
at least one among R 11 to R 21 is represented by Formula 2, and
M, X 1 , and X 2 are the same as defined in Formula 1.

8. The organic electroluminescence device of claim 7 , wherein the fused polycyclic compound represented by Formula 3 is represented by Formula 4:

wherein, in Formula 4,
R 31 to R 33 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R 31 to R 33 are optionally combined with an adjacent group to form a ring,
at least one among R 31 to R 33 is represented by Formula 2, and
M, X 1 , and X 2 are the same as defined in Formula 1.

9. The organic electroluminescence device of claim 1 , wherein
the substituent represented by Formula 2 is represented by Formula 5-1 or Formula 5-2:

wherein, in Formulae 5-1 and 5-2,
R 4 , R 5 , n 1 , and n 2 are the same as defined in Formula 2.

10. The organic electroluminescence device of claim 9 , wherein
the substituent represented by Formula 2 is represented by any one among Formula 6-1 to Formula 6-4:

wherein, in Formulae 6-1 to 6-4,
R 41 to R 46 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R 41 to R 46 are optionally combined with an adjacent group to form a ring,
n 3 and n 4 are each independently an integer of 0 to 3,
n 5 to n 8 are each independently an integer of 0 to 4,
m 1 and m 2 are each independently 0 or 1, and
at least one of m 1 and m 2 is 1.

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

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Hyoyoung
• Ko Soo-Byung
• Park Junha
• Pak Han Kyu
• Baek Jang Yeol
• Sim Mun-Ki
• Oh Chanseok

Classifications

• C07F5/027

  Organoboranes and organoborohydrides · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F5/00

  Compounds containing elements of Groups 3 or 13 of the Periodic Table · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title