Light emitting element

Patent metadata

Field	Value
Publication number	US-12428597-B2
Application number	US-202217584240-A
Country	US
Kind code	B2
Filing date	Jan 25, 2022
Priority date	Apr 7, 2021
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

A light emitting element of one or more embodiments includes a first electrode, a second electrode, and a polycyclic compound represented by Formula 1 below in an emission layer disposed between the first electrode and the second electrode, thereby showing high emission efficiency properties:

The polycyclic compound is of a DABNA structure includes one heteroaryl group substituted at a para position to boron, and two bulky substituents substituted at meta positions to the boron.

First claim

What is claimed is:

1. A light emitting element, comprising:
a first electrode;
a second electrode on the first electrode; and
an emission layer between the first electrode and the second electrode, the emission layer comprising a polycyclic compound represented by Formula 1,
wherein the first electrode and the second electrode each independently comprise at least one selected from among Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, Zn, compounds thereof, mixtures thereof, and oxides thereof:

in Formula 1,
“a” to “d” are each independently an integer of 0 to 4,
“m” is 0 or 1,
X 1 and X 2 are each independently O, S, Se, or NRa,
P 1 and P 2 are each independently a direct linkage, O, S, Se, NRb, or CRcRd,
at least one selected from among R 1 and R 2 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted t-butyl group, and remainder of R 1 and R 2 is a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 15 ring-forming carbon atoms,
R 3 to R 6 and Ra to Rd are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 6 carbon atoms, a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group of 2 to 15 ring-forming carbon atoms, or a substituted or unsubstituted amine group, and/or combined with an adjacent group to form a ring, and
Q 1 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, or a substituted or unsubstituted alkenyl group of 2 to 6 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring.

2. The light emitting element of claim 1 , wherein Formula 1 is represented by Formula 2-1 or Formula 2-2:

in Formula 2-1, “a”, “b”, P 1 , R 1 to R 4 , X 1 , X 2 , and Q 1 are the same as defined in Formula 1, and
in Formula 2-2, “a” to “d”, P 1 , P 2 , R 1 to R 6 , X 1 , X 2 , and Q 1 are the same as defined in Formula 1.

3. The light emitting element of claim 2 , wherein Formula 2-2 is represented by any one selected from among Formula 2A-1 to Formula 2A-6:

and
in Formulae 2A-1 to 2A-6, “a” to “d”, R 1 to R 6 , X 1 , X 2 , Rb to Rd, and Q 1 are the same as defined in Formula 1.

4. The light emitting element of claim 2 , wherein Formula 2-2 is represented by any one selected from among Formula 2B-1 to Formula 2B-15:

and
in Formulae 2B-1 to 2B-15, “a” to “d”, R 1 to R 6 , X 1 , X 2 , Q 1 , and Rb to Rd are the same as defined in Formula 1.

5. The light emitting element of claim 2 , wherein Formula 1 is represented by Formula 3-1 to Formula 3-4:

in Formula 3-4, Ra1 and Ra2 are a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 6 carbon atoms, a substituted or unsubstituted heteroaryl group of 2 to 15 ring-forming carbon atoms, or a substituted or unsubstituted amine group, and/or combined with an adjacent group to form a ring, and
in Formula 3-1 to Formula 3-4, “a” to “d”, “m”, P 1 , P 2 , R 1 to R 6 , and Q 1 are the same as defined in Formula 1.

6. The light emitting element of claim 1 , wherein Formula 1 is represented by any one selected from among Formula 4-1 to Formula 4-6:

and
in Formula 4-1 to Formula 4-6, “a” to “d”, “m”, P 1 , P 2 , R 1 to R 6 , Q 1 , and Ra are the same as defined in Formula 1.

7. The light emitting element of claim 1 , wherein Formula 1 is represented by any one selected from among Formula 5-1 to Formula 5-4:

and
in Formula 5-1 to Formula 5-4, “a” to “d”, “m”, P 1 , P 2 , R 3 to R 6 , X 1 , X 2 , and Q 1 are the same as defined in Formula 1.

8. The light emitting element of claim 1 , wherein Formula 1 is represented by any one selected from among Formula 6-1 to Formula 6-6:

and
in Formula 6-1 to Formula 6-6, “a” to “d”, “m”, P 1 , P 2 , R 1 to R 6 , X 1 , and X 2 are the same as defined in Formula 1.

9. The light emitting element of claim 1 , wherein, in Formula 1, at least one selected from among X 1 and X 2 is NRa, and
Ra is an unsubstituted biphenyl group, or an unsubstituted terphenyl group.

10. The light emitting element of claim 1 , wherein the polycyclic compound is represented by any one selected from among polycyclic compounds in the following Compound Group 1:

11. A light emitting element, comprising:
a first electrode;
a second electrode on the first electrode;
an emission layer between the first electrode and the second electrode, the emission layer comprising a polycyclic compound represented by Formula 1; and
a hole transport region between the first electrode and the emission layer, the hole transport region comprising the following Compound H-1-1:

in Formula 1,
“a” to “d” are each independently an integer of 0 to 4,
“m” is 0 or 1,
X 1 and X 2 are each indep

Assignees

• Samsung Display Co Ltd

Inventors

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

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K85/658 Primary

  Organoboranes · CPC title

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K2101/10

  Triplet emission · CPC title