Granted Patent B2

US 12,207,549 · App. 17/328,549 · Granted Jan 21, 2025

Inventor: Yuji Suzaki (Yokohama, JP)

Assignee: SAMSUNG DISPLAY CO., LTD.

H10K85/657H10K85/40H10K50/11H10K2101/10

Abstract

Claims (52)

1. An organic electroluminescence device, 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 and comprising a polycyclic compound represented by Formula 1:

wherein in Formula 1,

X is N or —C(R 11 ),

Y 1 and Y 2 are each independently —C═O, —C═S, or —S═O,

R 1 to R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or combined with an adjacent group to form a ring,

provided that:

two adjacent groups among R 1 , R 2 and R 11 are optionally combined to form a ring; or

two adjacent groups among R 3 to R 6 are optionally combined to form a ring,

R 7 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,

at least one of R 1 to R 11 is represented by Formula 2 or Formula 3, and

when at least one of R 1 to R 10 is represented by Formula 2, X is —C(R 11 ) and R 11 is a deuterium atom, a methyl group, an isopropyl group, a t-butyl group, a substituted amine group, or a substituted phenyl group, or combined with an adjacent group to form a ring:

wherein in Formula 2,

n is 0 or 1,

W 1 is a direct linkage, —B(R 29 ), —C═O, O, S, —SO, —SO 2 , —N(R 30 ), —P═O, —P(R 31 ), or —Si(R 32 )(R 33 ),

wherein in Formula 3,

Z is —B(R 56 ), —C═O, O, S, —SO, —SO 2 , —N(R 57 ), —P═O, —P(R 58 ), or —Si(R 59 )(R 60 ),

wherein in Formula 2 and Formula 3,

R 21 to R 33 , and R 51 to R 60 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or combined with an adjacent group selected from R 1 to R 6 , R 11 , R 21 to R 33 , and R 51 to R 60 to form a ring.

2. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by one of Formula 1-A1 to Formula 1-A6:

wherein in Formula 1-A1 to Formula 1-A6,

R 1 to R 11 , and X are the same as defined in Formula 1.

3. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by Formula 1-C:

wherein in Formula 1-C,

R 1 , R 2 , R 7 to R 10 , X, Y 1 , Y 2 , R 21 to R 28 , n, and W 1 are the same as defined in Formula 1 and Formula 2.

4. The organic electroluminescence device of claim 1 , wherein the organic electroluminescence device has an external quantum efficiency in a range of about 10% to about 20%, at a luminance of about 1,000 cd/m 2 .

5. The organic electroluminescence device of claim 1 , wherein the emission layer emits delayed fluorescence.

6. The organic electroluminescence device of claim 1 , wherein the emission layer comprises at least one polycyclic compound selected from Compound Group 1:

7. An organic electroluminescence device, 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 and comprising a polycyclic compound represented by Formula 1, wherein

the polycyclic compound has an external quantum efficiency in a range of about 10% to about 20% at a luminance of about 1,000 cd/m 2 :

wherein in Formula 1,

X is N or —C(R 11 ),

Y 1 and Y 2 are each independently —C═O, —C═S, or —S═O,

R 1 to R 6 , are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or combined with an adjacent group to form a ring,

provided that:

two adjacent groups among R 1 , R 2 , and R 11 are optionally to form a ring; or

two adjacent groups among R 3 to R 6 are optionally combined to form a ring,

R 7 to R 10 are each indecently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,

at least one of R 1 to R 11 is represented by Formula 2 or Formula 3, and

when at least one of R 1 to R 10 is represented by Formula 2, X is —C(R 11 ) and R 11 is a deuterium atom, a methyl group, a isopropyl group, a t-butyl group, a substituted amine group, or a substituted phenyl group, or combined with an adjacent group to form a ring:

wherein in Formula 2,

n is 0 or 1,

W 1 is a direct linkage, —B(R 29 ), —C═O, O, S, —SO, —SO 2 , —N(R 30 ), —P═O, —P(R 31 ), or —Si(R 32 )(R 33 ),

wherein in Formula 3,

Z is —B(R 56 ), —C═O, O, S, —SO, —SO 2 , —N(R 57 ), —P═O, —P(R 58 ), or —Si(R 59 )(R 60 ),

wherein in Formula 2 and Formula 3,

R 21 to R 33 , and R 51 to R 60 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or combined with an adjacent group selected from R 1 to R 6 , R 11 , R 21 to R 33 , and R 51 to R 60 to form a ring.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (23)