Granted Patent B2

US 12,565,614 · App. 17/775,330 · Granted Mar 3, 2026

Inventors: Ji-Young Kim (Yongin-si, KR); Jong-Su Lee (Yongin-si, KR); Jun-Tae Mo (Yongin-si, KR); Dong-Jun Kim (Yongin-si, KR)

Assignee: LT MATERIALS CO., LTD.

C09K11/06C07D307/91C07D307/93C07D333/78H10K85/631H10K85/636H10K85/654H10K85/6572H10K85/6574H10K85/6576C09K2211/1018H10K50/11H10K2101/90

Abstract

Claims (56)

1 . A heterocyclic compound represented by the following Chemical Formula 1-B:

wherein, in Chemical Formula 1-B,

X is O; or S;

R1 to R5 are hydrogen;

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;

L1 is any one of the following structural formulae:

in the structural formulae,

X1 is O; or S;

L3 and L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;

Z3 and Z4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and a substituted or unsubstituted amine group;

a and b are an integer of 0 to 5;

c and d are an integer of 1 to 6;

m is an integer of 1 to 4, and s is an integer of 0 to 3.

2 . The heterocyclic compound claim 1 , wherein Chemical Formula 1-B is represented by any one of the following Chemical Formulae 1-1-B to 1-4-B:

in Chemical Formulae 1-1-B to 1-4-B,

R1 to R5, X, Ar1, Ar2, L1, L3, L4, Z3, Z4, m, a, b, c, d and s have the same definitions as in Chemical Formula 1-B.

3 . The heterocyclic compound of claim 1 , wherein Chemical Formula 1-B is represented by any one of the following compounds:

4 . An organic light emitting device comprising:

a first electrode;

a second electrode provided opposite to the first electrode; and

one or more organic material layers provided between the first electrode and the second electrode,

wherein one or more layers of the organic material layers comprise the heterocyclic compound of claim 1 .

5 . The organic light emitting device of claim 4 , wherein the organic material layer comprising the heterocyclic compound of Chemical Formula 1-B further comprises a heterocyclic compound represented by the following Chemical Formula 2:

in Chemical Formula 2,

X11 is O; or S;

R21 to R25 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and —NRR′, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heteroring;

L11 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;

Z11 and Z22 are the same as or different from each other, and each independently selected from the group consisting of a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and a substituted or unsubstituted amine group;

R and R′ are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;

m1 and m2 are an integer of 0 to 4;

s1 is an integer of 0 to 2; and

n1 and n2 are an integer of 1 to 6.

6 . The organic light emitting device of claim 5 , wherein Chemical Formula 2 is any one of the following compounds:

7 . The organic light emitting device of claim 4 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the heterocyclic compound.

8 . The organic light emitting device of claim 4 , wherein the organic material layer comprises a light emitting layer, the light emitting layer comprises a host material, and the host material comprises the heterocyclic compound.

9 . The organic light emitting device of claim 4 , further comprising one, two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer, an electron transfer layer, an electron blocking layer and a hole blocking layer.

10 . A composition for an organic material layer of an organic light emitting device, the composition comprising:

the heterocyclic compound of claim 1 ; and

a heterocyclic compound represented by the following Chemical Formula 2:

wherein, in Chemical Formula 2,

X11 is O; or S;

R21 to R25 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and —NRR′, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heteroring;

L11 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;

Z11 and Z22 are the same as or different from each other, and each independently selected from the group consisting of a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and a substituted or unsubstituted amine group;

R and R′ are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;

m1 and m2 are an integer of 0 to 4;

s1 is an integer of 0 to 2; and

n1 and n2 are an integer of 1 to 6.

11 . The composition for an organic material layer of an organic light emitting device of claim 10 , wherein the heterocyclic compound represented by Chemical Formula 1-B and the heterocyclic compound represented by Chemical Formula 2 have a weight ratio of 1:10 to 10:1 in the composition.

12 . A method for manufacturing an organic light emitting device, the method comprising:

preparing a substrate;

forming a first electrode on the substrate;

forming one or more organic material layers on the first electrode; and

forming a second electrode on the organic material layer,

wherein the forming of organic material layers comprises forming one or more organic material layers using the composition for an organic material layer of claim 10 .

13 . The method for manufacturing an organic light emitting device of claim 12 , wherein the forming of organic material layers is forming using a thermal vacuum deposition method after pre-mixing the heterocyclic compound of Chemical Formula 1-B and the heterocyclic compound of Chemical Formula 2.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (14)