IP Library Granted Patent US 12690382
Granted Patent B2
US 12690382 · App. 17/862,923 · Granted Jul 21, 2026

Light emitting element and polycyclic compound for the same

Inventors: Mi Eun Jun (Hwaseong-si, KR); Seran Kim (Suwon-si, KR); Chanseok Oh (Seoul, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/322C07F5/027C09K11/06H10K85/346H10K85/633H10K85/654H10K85/658H10K85/701C09K2211/1014H10K50/121H10K50/15H10K50/16H10K59/122H10K2101/90H10K2102/351
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12690382
App. No.
17/862,923
Granted
Jul 21, 2026
Kind
B2
Abstract

A light emitting element according to an embodiment includes a first electrode, a second electrode disposed on the first electrode, and an emission layer disposed between the first electrode and the second electrode. The emission layer includes a first compound, and at least one of a second compound, a third compound, and a fourth compound. The first compound is represented by Formula 1, the second compound is represented by Formula HT-1, the third compound is represented by Formula ET-1, and the fourth compound is represented by Formula M-b. Accordingly, the light emitting element has decreased driving voltage and improved efficiency.

Claims (164)

1 . A light emitting element comprising:

a first electrode;

a second electrode disposed on the first electrode; and

an emission layer disposed between the first electrode and the second electrode, wherein

the emission layer comprises:

a first compound represented by Formula 1 and having a luminescence center wavelength in a range of about 440 nm to about 480 nm; and

at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, or a fourth compound represented by Formula M-b:

wherein in Formula 1,

X 1 and X 2 are each independently N(R 0 ), O, or S,

R 0 is 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 hydrocarbon ring group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms,

at least one of R 1 to R 4 , R 11 to R 14 , and R 21 to R 23 is each independently a group represented by Formula 2, and

the remainder of R 1 to R 4 , R 11 to R 14 , and R 21 to R 23 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 hydrocarbon ring group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms:

wherein in Formula 2,

X 3 and X 4 are each independently N(R 8 ), O, or S,

a1 and a2 are each independently an integer from 0 to 4,

a3 is an integer from 0 to 2,

R 5 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, and

 represents a binding site to a neighboring atom:

wherein in Formula HT-1,

a4 is an integer from 0 to 8, and

R 9 and R 10 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms:

wherein in Formula ET-1,

at least one of Y 1 to Y 3 is N,

the remainder of Y 1 to Y 3 are each independently C(R a ),

R a is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms,

b1 to b3 are each independently an integer from 0 to 10,

L 1 to L 3 are each independently 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, and

Ar 1 to Ar 3 are each independently a hydrogen atom, a deuterium 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:

wherein in Formula M-b,

Q 1 to Q 4 are each independently C or N,

C 1 to C 4 are each independently a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 ring-forming carbon atoms,

e1 to e4 are each independently 0 or 1,

L 21 to L 24 are each independently a direct linkage,

 a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, 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,

d1 to d4 are each independently an integer from 0 to 4, and

R 31 to R 39 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, or are bonded to an adjacent group to form a ring.

2 . The light emitting element of claim 1 , wherein the group represented by Formula 2 is represented by one of Formula 2-1 to Formula 2-4:

wherein in Formula 2-1 to Formula 2-3,

a10 is an integer from 0 to 3,

wherein in Formula 2-4,

a11 is 0 or 1, and

wherein in Formula 2-1 to Formula 2-4,

a1 to a3, R 5 to R 7 , X 3 , and X 4 are each the same as defined in Formula 2, and

 represents a binding site to a neighboring atom.

3 . The light emitting element of claim 1 , wherein the group represented by Formula 2 is represented by one of Formula 2-A to Formula 2-F:

wherein in Formula 2-A to Formula 2-F,

a1 to a3 and R 5 to R 8 are each the same as defined in Formula 2, and

 represents a binding site to a neighboring atom.

4 . The light emitting element of claim 1 , wherein the first compound represented by Formula 1 is represented by one of Formula 1-1 to Formula 1-5:

wherein in Formula 1-1 to Formula 1-3,

R 41 and R 42 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 hydrocarbon ring group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and

wherein in Formula 1-1 to Formula 1-5,

R 1 to R 4 , R 11 to R 14 , and R 21 to R 23 are each the same as defined in Formula 1.

5 . The light emitting element of claim 4 , wherein R 41 and R 42 are each independently a group represented by one of R11-1 to R11-6:

wherein in R11-1, R11-2, and R11-4,

Ph is a phenyl group, and

wherein in R11-1 to R11-6,

 represents a binding site to a neighboring atom.

6 . The light emitting element of claim 1 , wherein the first compound represented by Formula 1 is represented by one of Formula 1-A to Formula 1-C:

wherein in Formula 1-B,

X 13 and X 14 are each independently N(R 18 ), O, or S,

a11 is an integer from 0 to 3,

a12 is an integer from 0 to 4,

a13 is an integer from 0 to 2, and

R 15 to R 18 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms,

wherein in Formula 1-C,

X 23 and X 24 are each independently N(R 28 ), O, or S,

a21 and a22 are each independently an integer from 0 to 4,

a23 is 0 or 1, and

R 25 to R 28 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, and

wherein in Formula 1-A to Formula 1-C,

a10 is an integer from 0 to 3, and

a2, a3, R 1 to R 7 , R 11 to R 14 , R 21 , R 23 , and X 1 to X 4 are each the same as defined in Formula 1.

7 . The light emitting element of claim 1 , wherein R 5 to R 7 are each independently a substituted methyl group, an unsubstituted t-butyl group, an unsubstituted triphenylsilyl group, or a substituted or unsubstituted phenyl group.

8 . The light emitting element of claim 1 , wherein at least a remaining one of R 1 to R 4 , R 11 to R 14 , and R 21 to R 23 which is not a group represented by Formula 2 is each independently a group represented by one of R1-1 to R1-3:

wherein in R1-1,

a51 is an integer from 0 to 8, and

R 51 is a hydrogen atom, a deuterium atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and

wherein in R1-2,

a52 and a53 are each independently an integer from 0 to 5, and

R 52 and R 53 each independently a hydrogen atom, a deuterium atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and

wherein in R1-1 to R1-3,

 represents a binding site to a neighboring atom.

9 . The light emitting element of claim 1 , wherein at least one of R 1 to R 4 , R 11 to R 14 , and R 21 to R 23 comprises a deuterium atom.

10 . The light emitting element of claim 1 , further comprising a hole transport region disposed between the first electrode and the emission layer, wherein

the hole transport region comprises a hole transport compound represented by Formula H-1:

wherein in Formula H-1,

c1 and c2 are each independently an integer from 0 to 10,

L 11 and L 12 are each independently 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,

Ar 11 and Ar 12 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

Ar 13 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

11 . The light emitting element of claim 1 , wherein the emission layer comprises the first compound, the second compound, and the third compound.

12 . The light emitting element of claim 1 , wherein the emission layer comprises the first compound, the second compound, the third compound, and the fourth compound.

13 . The light emitting element of claim 1 , wherein the first compound is selected from Compound Group 1:

wherein in Compound Group 1,

D is a deuterium atom, and

Ph is a phenyl group.

14 . The light emitting element of claim 1 , wherein

the second compound is selected from Compound Group 2,

the third compound is selected from Compound Group 3, and

the fourth compound is selected from Compound Group 4:

wherein in Compound Group 4,

R, R 38 , and R 39 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, 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.

15 . A polycyclic compound represented by Formula 1:

wherein in Formula 1,

X 1 and X 2 are each independently N(R 0 ), O, or S,

R 0 is 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 hydrocarbon ring group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms,

at least one of R 1 to R 4 , R 11 to R 14 , and R 21 to R 23 is each independently a group represented by Formula 2, and

the remainder of R 1 to R 4 , R 11 to R 14 , and R 21 to R 23 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 hydrocarbon ring group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms:

wherein in Formula 2,

X 3 and X 4 are each independently N(R 8 ), O, or S,

a1 and a2 are each independently an integer from 0 to 4,

a3 is an integer from 0 to 2,

R 5 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, and

 represents a binding site to a neighboring atom, and

wherein the polycyclic compound has a luminescence center wavelength in a range of about 440 nm to about 480 nm.

16 . The polycyclic compound of claim 15 , wherein the group represented by Formula 2 is represented by one of Formula 2-1 to Formula 2-4:

wherein in Formula 2-1 to Formula 2-3,

a10 is an integer from 0 to 3,

wherein in Formula 2-4,

a11 is 0 or 1, and

wherein in Formula 2-1 to Formula 2-4,

a1 to a3, R 5 to R 7 , X 3 , and X 4 are each the same as defined in Formula 2, and

represents a binding site to a neighboring atom.

17 . The polycyclic compound of claim 15 , wherein the group represented by Formula 2 is represented by one of Formula 2-A to Formula 2-F:

wherein in Formula 2-A to Formula 2-F,

a1 to a3 and R 5 to R 8 are each the same as defined in Formula 2, and

 represents a binding site to a neighboring atom.

18 . The polycyclic compound of claim 15 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 1-1 to Formula 1-5:

wherein in Formula 1-1 to Formula 1-3,

R 41 and R 42 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 hydrocarbon ring group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and

wherein in Formula 1-1 to Formula 1-5,

R 1 to R 4 , R 11 to R 14 , and R 21 to R 23 are each the same as defined in Formula 1.

19 . The polycyclic compound of claim 15 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 1-A to Formula 1-C:

wherein in Formula 1-B,

X 13 and X 14 are each independently N(R 18 ), O, or S,

a11 is an integer from 0 to 3,

a12 is an integer from 0 to 4,

a13 is an integer from 0 to 2, and

R 15 to R 18 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms,

wherein in Formula 1-C,

X 23 and X 24 are each independently N(R 28 ), O, or S,

a21 and a22 are each independently an integer from 0 to 4,

a23 is 0 or 1, and

R 25 to R 28 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, and

wherein in Formula 1-A to Formula 1-C,

a10 is an integer from 0 to 3, and

a2, a3, R 1 to R 7 , R 11 to R 14 , R 21 , R 23 , and X 1 to X 4 are each the same as defined in Formula 1.

20 . The polycyclic compound of claim 15 , wherein R 5 to R 7 are each independently a substituted methyl group, an unsubstituted t-butyl group, an unsubstituted triphenylsilyl group, or a substituted or unsubstituted phenyl group.

21 . The polycyclic compound of claim 15 , wherein at least a remaining one of R 1 to R 4 , R 11 to R 14 , and R 21 to R 23 which is not a group represented by Formula 2 is each independently a group represented by one of R1-1 to R1-3:

wherein in R1-1,

a51 is an integer from 0 to 8, and

R 51 is a hydrogen atom, a deuterium atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

wherein in R 1 -2,

a52 and a53 are each independently an integer from 0 to 5, and

R 52 and R 53 each independently a hydrogen atom, a deuterium atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and

wherein in R1-1 to R1-3,

 represents a binding site to a neighboring atom.

22 . The polycyclic compound of claim 15 , wherein the polycyclic compound represented by Formula 1 is a thermally activated delayed fluorescence material.

23 . The polycyclic compound of claim 15 , wherein the polycyclic compound has an oscillator strength (f) in a range of about 0.25 to about 0.60.

24 . A polycyclic compound selected from Compound Group 1:

wherein in Compound Group 1,

D is a deuterium atom, and

Ph is a phenyl group.