Granted Patent B2

US 12,426,499 · App. 17/102,168 · Granted Sep 23, 2025

Inventors: Hirokazu Kuwabara (Yokohama, JP); Ryuhei Furue (Yokohama, JP)

Assignee: Samsung Display Co., Ltd.

H10K85/636H10K85/211H10K85/622H10K85/631H10K85/6572H10K85/6574H10K85/6576H10K85/658H10K50/15H10K50/16H10K50/81H10K50/82H10K2101/20

Abstract

Claims (70)

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 each independently comprise any one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Zn, Sn, and Yb, a compound of two or more thereof, a mixture of two or more thereof, or at least one oxide thereof, and

at least one organic layer among the plurality of organic layers comprises a fused polycyclic compound represented by any one selected from among Formula 3-1 to Formula 3-5:

wherein, in Formula 3-1 to Formula 3-5,

A 1 to A 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxy 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, and/or are bonded to an adjacent group to form a ring; and

B 1 and B 2 , B 3 and B 4 , and B 5 and B 6 are each fused to a substituent represented by Formula 2:

Formula 2

wherein, in Formula 2,

is a position of fusion to one of the two or more pairs selected from among B 1 and B 2 , B 3 and B 4 , and B 5 and B 6 ;

X 1 and X 2 are each independently NAr 1 , O, or S;

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/or is bonded to an adjacent group to form a ring;

R a and R b are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino 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;

n 1 is an integer of 0 to 4; and

n 2 is an integer of 0 to 3.

2. The organic electroluminescence device of claim 1 , wherein the plurality of organic layers comprises:

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

wherein the emission layer comprises the fused polycyclic compound.

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 host and a dopant, and the dopant comprises the fused polycyclic compound represented by one selected from among Formula 3-1 to Formula 3-5.

5. The organic electroluminescence device of claim 1 , wherein two or three substituents represented by Formula 2 are fused to the fused polycyclic compound represented by one selected from among Formula 3-1 to Formula 3-5, and the two or three fused substituents represented by Formula 2 are the same as each other.

6. The organic electroluminescence device of claim 1 , wherein the substituent represented by Formula 2 is represented by any one selected from Formula 2-1 to Formula 2-8:

wherein, in Formula 2-1 to Formula 2-8,

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/or are bonded to an adjacent group to form a ring and

R a and R b , and n 1 and n 2 are each independently the same as defined in Formula 2.

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

wherein, in Formula 2-a,

X 1 and X 2 , and R a and R b are each independently the same as defined in Formula 2.

8. The organic electroluminescence device of claim 1 , wherein the fused polycyclic compound represented by one selected from among Formula 3-1 to Formula 3-5 is represented by any one selected from among Formula 4-1 to Formula 4-8:

wherein, in Formula 4-1 to Formula 4-8,

X 11 , X 12 , X 13 , X 21 , X 22 , and X 23 are each independently NAr 1 , O, or S;

R a1 , R a2 , R a3 , R b1 , R b2 , and R b3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino 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, and/or are bonded to an adjacent group to form a ring;

n 11 , n 12 , and n 13 are each independently an integer of 0 to 4;

n 21 , n 22 , and n 23 are each independently an integer of 0 to 3; and

Ar 1 and A 1 to A 8 are each independently the same as defined in Formula 2 and Formula 3-1 to Formula 3-5.

9. The organic electroluminescence device of claim 1 , wherein R a and R b are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

10. The organic electroluminescence device of claim 1 , wherein A 1 to A 8 are each independently a hydrogen atom or a deuterium atom.

11. The organic electroluminescence device of claim 1 , further comprising a capping layer on the second electrode and having a refractive index of about 1.6 or more.

12. The organic electroluminescence device of claim 1 , wherein the fused polycyclic compound represented by one selected from among Formula 3-1 to Formula 3-5 is at least one selected from compounds represented by Compound Group 1:

13. A fused polycyclic compound represented by any one selected from among Formula 3-1 to Formula 3-5:

wherein, in Formula 3-1 to Formula 3-5,

A 1 to A 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxy 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, and/or are bonded to an adjacent group to form a ring; and

B 1 and B 2 , B 3 and B 4 , and B 5 and B 6 are each fused to a substituent represented by Formula 2:

wherein, in Formula 2,

is a position of fusion to one of the two or more pairs selected from among B 1 and B 2 , B 3 and B 4 , and B 5 and B 6 ;

X 1 and X 2 are each independently NAr 1 , O, or S;

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/or is bonded to an adjacent group to form a ring;

R a and R b are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino 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;

n 1 is an integer of 0 to 4; and

n 2 is an integer of 0 to 3.

14. The fused polycyclic compound of claim 13 , wherein two or three substituents represented by Formula 2 are fused to the fused polycyclic compound represented by one selected from among Formula 3-1 to Formula 3-5, and the two or three fused substituents represented by Formula 2 are the same as each other.

15. The fused polycyclic compound of claim 13 , wherein the substituent represented by Formula 2 is represented by any one selected from Formula 2-1 to Formula 2-8:

wherein, in Formula 2-1 to Formula 2-8,

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/or are bonded to an adjacent group to form a ring; and

R a and R b , and n 1 and n 2 are each independently the same as defined in Formula 2.

16. The fused polycyclic compound of claim 13 , wherein the substituent represented by Formula 2 is represented by Formula 2-a:

wherein, in Formula 2-a,

X 1 and X 2 , and R a and R b are each independently the same as defined in Formula 2.

17. The fused polycyclic compound of claim 13 , wherein the fused polycyclic compound represented by one selected from among Formula 3-1 to Formula 3-5 is represented by any one selected from Formula 4-1 to Formula 4-8:

wherein, in Formula 4-1 to Formula 4-8,

X 11 , X 12 , X 13 , X 21 , X 22 , and X 23 are each independently NAr 1 , O, or S;

R a1 , R a2 , R a3 , R b1 , R b2 , and R b3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino 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, and/or are bonded to an adjacent group to form a ring;

n 11 , n 12 , and n 13 are each independently an integer of 0 to 4;

n 21 , n 22 , and n 23 are each independently an integer of 0 to 3; and

Ar 1 and A 1 to A 8 are each independently the same as defined in Formula 2 and Formula 3-1 to Formula 3-5.

18. The fused polycyclic compound of claim 13 , wherein the fused polycyclic compound represented by one selected from among Formula 3-1 to Formula 3-5 is at least one selected from compounds represented by Compound Group 1:

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (19)