Granted Patent B2

US 12,588,409 · App. 17/494,522 · Granted Mar 24, 2026

Inventor: Akinori Yamatani (Yokohama, JP)

Assignee: Samsung Display Co., Ltd.

H10K85/631H10K85/40H10K85/626H10K85/6572H10K85/6574H10K85/6576H10K85/658H10K50/11H10K50/181H10K2101/10

Abstract

Claims (116)

1 . A light emitting element comprising:

a first electrode;

a second electrode disposed on the first electrode; and

at least one functional layer disposed between the first electrode and the second electrode and comprising a nitrogen-containing compound represented by Formula 1:

wherein in Formula 1,

n1 is an integer from 0 to 2,

L 1 is 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 1 is 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 2 is a group represented by one of Ar2-1 to Ar2-6,

R 1 , R 2 and R 4 to R 7 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring-forming carbon atoms, or are bonded to an adjacent group to form a ring,

Ar 2 and R 3 are the same,

Q 1 is O, S, SO, Se, CO, C(R 11 )(R 12 ), B(R 13 ), P(R 15 ), PO(R 16 ), PS(R 17 ), or a group represented by Formula 3,

R 11 and R 12 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, or are bonded to an adjacent group to form a ring, and

R 13 and R 15 to R 17 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms:

wherein in Ar2-1,

a21 is an integer from 0 to 5,

a22 is an integer from 0 to 4, and

R 51 and R 52 are each independently a hydrogen atom, a deuterium atom, or an unsubstituted phenyl group,

wherein in Ar2-4,

a23 is 0 or 1, and

W 1 is N(Ph), O, or S,

wherein in Ar2-5 and Ar2-6,

one of W 2 or W 3 is a direct linkage, and

the other of W 2 and W 3 is N(Ph), O, or S, and

wherein in Ar2-4 to Ar2-6,

Ph is a phenyl group,

wherein in Formula 3,

W 1 is C, Si, or Ge, and is the same as Q 1 ,

m1 is 0 or 1,

Z 1 is a direct linkage, C(R 32 )(R 33 ), N(R 34 ), O, or S,

a1 is an integer from 0 to 8,

R 31 to R 34 are each independently a hydrogen atom, a deuterium atom, 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,

when R 3 is a hydrogen atom, Aris a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted dibenzosilole group, and

when Ar 2 is a group represented by Ar2-1, Q 1 is a group represented by Formula 3, and Z 1 is a direct linkage or N(R 34 ).

2 . The light emitting element of claim 1 , wherein Ar 1 is a group represented by one of Ar1-1 to Ar1-9:

wherein in Ar1-1,

a11 is an integer from 0 to 5,

wherein in Ar1-4 and Ar1-5,

a12 and a13 are each independently an integer from 0 to 7,

wherein in Ar1-8,

a14 and a15 are each independently an integer from 0 to 5, and

a16 is an integer from 0 to 7,

wherein in Ar1-9,

a17 is an integer from 0 to 8, and

wherein in Ar1-1, Ar1-4 to Ar1-6, Ar1-8, and Ar1-9,

R 41 to R 48 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

3 . The light emitting element of claim 1 , wherein the nitrogen-containing compound represented by Formula 1 is represented by one of Formula 1-1 to Formula 1-3:

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

Ar 1 , Ar 2 , L 1 , n1, R 1 to R 7 , a1, R 31 , m1, and Z1 are the same as defined in connection with Formula 1.

4 . The light emitting element of claim 3 , wherein the nitrogen-containing compound represented by Formula 1-1 is represented by one of Formula 1-1A to Formula 1-1E:

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

Ar 1 , Ar 2 , L 1 , n1, R 1 to R 7 , a1, and R 31 to R 34 are the same as defined in connection with Formula 1.

5 . The light emitting element of claim 1 , wherein at least one of R 1 , R 2 and R 4 to R 7 is a deuterium atom.

6 . The light emitting element of claim 1 , wherein

the at least one functional layer comprises:

a hole injection layer disposed on the first electrode;

a hole transport layer disposed on the hole injection layer;

an electron blocking layer disposed on the hole transport layer; and

an emission layer disposed on the electron blocking layer, and

at least one of the hole injection layer, the hole transport layer, the electron blocking layer, and the emission layer comprises the nitrogen-containing compound.

7 . A light emitting element comprising:

a first electrode;

a second electrode disposed on the first electrode; and

at least one functional layer disposed between the first electrode and the second electrode and comprising a nitrogen-containing compound selected from Compound Group 1:

8 . A nitrogen-containing compound represented by Formula 1:

wherein in Formula 1,

n1 is an integer from 0 to 2,

L 1 is 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 1 is 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 2 is a group represented by one of Ar2-1 to Ar2-6:

R 1 , R 2 and R 4 to R 7 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring-forming carbon atoms, or are bonded to an adjacent group to form a ring,

Ar 2 and R 3 are the same,

Q 1 is O, S, SO, Se, CO, C(R 11 )(R 12 ), B(R 13 ), P(R 15 ), PO(R 16 ), PS(R 17 ), or a group represented by Formula 3,

R 11 and R 12 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, or are bonded to an adjacent group to form a ring, and

R 13 and R 15 to R 17 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms:

wherein in Ar2-1,

a21 is an integer from 0 to 5,

a22 is an integer from 0 to 4, and

R 51 and R 52 are each independently a hydrogen atom, a deuterium atom, or an unsubstituted phenyl group,

wherein in Ar2-4,

a23 is 0 or 1, and

W 1 is N(Ph), O, or S,

wherein in Ar2-5 and Ar2-6,

one of W 2 or W 3 is a direct linkage, and

the other of W 2 and W 3 is N(Ph), O, or S, and

wherein in Ar2-4 to Ar2-6,

Ph is a phenyl group,

wherein in Formula 3,

W 1 is C, Si, or Ge,

m1 is 0 or 1, and

Z 1 is a direct linkage, C(R 32 )(R 33 ), N(R 34 ), O, or S,

a1 is an integer from 0 to 8,

R 31 to R 34 are each independently a hydrogen atom, a deuterium atom, 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,

when R 3 is a hydrogen atom, Ar 1 is a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted dibenzosilole group, and

when Ar 2 is a group represented by Ar2-1, Q 1 is a group represented by Formula 3, and Z 1 is a direct linkage or N(R 34 ).

9 . The nitrogen-containing compound of claim 8 , wherein Ar 1 is a group represented by one of Ar1-1 to Ar1-9:

wherein in Ar1-1,

a11 is an integer from 0 to 5,

wherein in Ar1-4 and Ar1-5,

a12 and a13 are each independently an integer from 0 to 7,

wherein in Ar1-8,

a14 and a15 are each independently an integer from 0 to 5, and

a16 is an integer from 0 to 7,

wherein in Ar1-9,

a17 is an integer from 0 to 8, and

wherein in Ar1-1, Ar1-4 to Ar1-6, Ar1-8, and Ar1-9,

R 41 to R 48 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

10 . The nitrogen-containing compound of claim 8 , wherein the nitrogen-containing compound represented by Formula 1 is represented by one of Formula 1-1 to Formula 1-3:

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

Ar 1 , Ar 2 , L 1 , n1, R 1 to R 7 , a1, R 31 , m1, and Z 1 are the same as defined in connection with Formula 1.

11 . The nitrogen-containing compound of claim 10 , wherein the nitrogen-containing compound represented by Formula 1-1 is represented by one of Formula 1-1A to Formula 1-1E:

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

Ar 1 , Ar 2 , L 1 , n1, R 1 to R 7 , a1, and R 31 to R 34 are the same as defined in connection with Formula 1.

12 . The nitrogen-containing compound of claim 8 , wherein at least one of R 1 , R 2 and R 4 to R 7 is a deuterium atom.

13 . The nitrogen-containing compound of claim 8 , wherein the nitrogen-containing compound is bilaterally symmetrical with respect to the nitrogen atom (N) in Formula 1.

14 . The nitrogen-containing compound of claim 8 , wherein the nitrogen-containing compound represented by Formula 1 is one selected from Compound Group 1:

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (78)