Organic electroluminescence device and polycyclic compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-12448564-B2
Application number	US-202016780744-A
Country	US
Kind code	B2
Filing date	Feb 3, 2020
Priority date	Apr 12, 2019
Publication date	Oct 21, 2025
Grant date	Oct 21, 2025

Abstract

An organic electroluminescence device having high luminous efficiency 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, wherein the emission layer includes a polycyclic compound represented by Formula 1 to achieve high luminous efficiency.

First claim

What is claimed is:

1. An organic electroluminescence 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 first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/AI, 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 thereof, and
wherein the emission layer includes a polycyclic compound represented by Formula 1:

in Formula 1,
X is a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 ring-forming carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 ring-forming 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,
Y 1 to Y 20 are each independently CR 1 or N, wherein at least one selected from Y 1 to Y 20 is N, and
R 1 is a hydrogen atom, a deuterium atom, a halogen atom, a boron group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 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, or is bonded to an adjacent group to form a ring,
wherein the polycyclic compound represented by Formula 1 is a thermally delayed fluorescence material, and
wherein a difference ΔE ST between a lowest singlet energy level and a lowest triplet energy level of the polycyclic compound represented by Formula 1 is 0.1 eV or less.

2. The organic electroluminescence device of claim 1 , wherein the emission layer emits blue light.

3. The organic electroluminescence device of claim 1 , wherein at least one selected from Y 1 to Y 15 is N.

4. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by any one selected from Formulae 2-1 to 2-3:

in Formulae 2-1 to 2-3,
Z 1 to Z 10 are each independently N or CR 2 ,
wherein R 2 is a hydrogen atom, a deuterium atom, a halogen atom, a boron group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 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, or is bonded to an adjacent group to form a ring, and
Y 1 to Y 20 are the same as defined with respect to Formula 1.

5. The organic electroluminescence device of claim 4 , wherein at least one selected from Y 1 and Y 2 in Formulae 2-1 and 2-2 is N.

6. The organic electroluminescence device of claim 4 , wherein Y 1 in Formula 2-3 is N.

7. The organic electroluminescence device of claim 4 , wherein Formula 2-1 is represented by Formula 3-1 or 3-2:

in Formulae 3-1 and 3-2,
Y 1 to Y 6 , Y 8 to Y 14 , Y 16 to Y 20 , and Z 1 to Z 5 are the same as defined with respect to Formula 2-1.

8. The organic electroluminescence device of claim 4 , wherein Formula 2-1 is represented by Formula 4:

in Formula 4,
Y 1 to Y 7 , Y 16 to Y 20 , and Z 1 to Z 5 are the same as defined with respect to Formula 2-1.

9. The organic electroluminescence device of claim 4 , wherein Formula 2-2 is represented by Formula 5:

in Formula 5,
Y 1 to Y 6 , Y 8 to Y 14 , Y 16 to Y 20 , and Z 1 to Z 10 are the same as defined with respect to Formula 2-2.

10. The organic electroluminescence device of claim 4 , wherein Formula 2-3 is represented by Formula 6:

in Formula 6,
Y 1 , Y 3 to Y 20 , Z 1 to Z 4 , and Z 7 to Z 9 are the same as defined with respect to Formula 2-3.

11. The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is any one selected from compounds represented by Compound Group 1:

12. A polycyclic compound represented by Formula 1:

in Formula 1,
X is a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 ring-forming carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 ring-forming 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,
Y 1 to Y 20 are each independently CR 1 or N, wherein at least one selected from Y 1 to Y 20 is N, and
R 1 is a hydrogen atom, a deuterium atom, a halogen atom, a boron group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 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, or is bonded to an adjacent group to form a ring,
wherein the polycyclic compound represented by Formula 1 is a thermally delayed fluorescence material, and
wherein a difference ΔE ST between a lowest singlet energy level and a lowest triplet energy level of the polycyclic compound represented by Formula 1 is 0.1 eV or less.

13. The polycyclic compound of claim 12 , wherein Formula 1 is represented by any one selected from Formulae 2-1 to 2-3:

in Formulae 2-1 to 2-3,
Z 1 to Z 10 are each independently N or CR 2 ,
wherein R 2 is a hydrogen atom, a deuterium atom, a halogen atom

Assignees

• Samsung Display Co Ltd

Inventors

• Ahn Heechoon
• Ko Soo-Byung
• Kim Hyeongmin
• Um Hyunah
• Lee Yeseul
• Im Yirang

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K85/658 Primary

  Organoboranes · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title