KR-20260062867-A - HETEROCYCLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE AND COMPOSITION FOR ORGANIC MATERIAL LAYER OF ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME

KR20260062867AKR 20260062867 AKR20260062867 AKR 20260062867AKR-20260062867-A

Abstract

The present invention relates to a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer of an organic light-emitting device.

Inventors

최의정
김동준
노영석
이현주
최대혁

Assignees

엘티소재주식회사

Dates

Publication Date: 20260507
Application Date: 20251027
Priority Date: 20241028

Claims (16)

Heterocyclic compounds represented by the following chemical formula 1: [Chemical Formula 1] X and Y are equal to or different from each other and are each independently O, S, NR, or CR'R'', and R, R' and R'' are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, and R1 to R4 are the same or different from one another and are each independently hydrogen; deuterium; 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, and Ar1 is a substituted or unsubstituted C6 to C60 aryl group, and r1 is an integer from 1 to 10, and if r1 is 2 or more, R1 are the same or different from each other, and r2 is an integer from 1 to 6, and if r2 is 2 or more, R2 are the same or different from each other, and r3 is an integer from 0 to 4, and if r3 is 2 or greater, R3 are the same or different from each other, and r4 is an integer from 0 to 5, and if r4 is 2 or greater, R4 are the same or different from each other, and The deuterium substitution rate of the compound of Chemical Formula 1 above is greater than 0% and less than or equal to 100%.
In claim 1, the formula 1 A heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-1 to 1-6, X, R1 and r1 are identical to the definitions in Chemical Formula 1 above.
A heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-7 to 1-12: [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] In the above chemical formulas 1-7 to 1-12, X and Y are identical to the definitions in Chemical Formula 1 above, and Ar2 is a C6 to C60 aryl group, and [D] represents deuterium substitution, n1 is 1 to 10, and n2 is 3 to 11.
A heterocyclic compound according to claim 1, wherein Ar1 is a substituted or unsubstituted C6 to C20 aryl group.
A heterocyclic compound according to claim 1, wherein R1 to R4 are the same or different from each other and each independently is hydrogen; or deuterium.
A heterocyclic compound according to claim 1, wherein the deuterium substitution rate of the compound of formula 1 is 10 to 80%.
In claim 1, The above chemical formula 1 is a heterocyclic compound represented by any one of the following compounds: .
An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a heterocyclic compound according to any one of claims 1 to 7.
An organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound.
An organic light-emitting device according to claim 9, wherein the light-emitting layer comprises a host material, and the host material comprises the heterocyclic compound.
An organic light-emitting device according to claim 10, wherein the host material further comprises a heterocyclic compound represented by the following chemical formula 2 or chemical formula 3: [Chemical Formula 2] In Chemical Formula 2, R21 and R22 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R7 and R8 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; 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, and r7 and r8 are each integers from 0 to 7, and if r7 is 2 or more, R7 are the same or different from each other, and if r8 is 2 or more, R8 are the same or different from each other, and [Chemical Formula 3] In Chemical Formula 3, A is a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, and R23 and R24 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R9 and R10 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; 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, and r9 and r10 are each integers from 0 to 4, and if r9 is 2 or more, R9 are the same or different from each other, and if r10 is 2 or more, R10 are the same or different from each other.
An organic light-emitting device according to claim 11, wherein the chemical formula 2 is represented by any one of the following compounds: .
An organic light-emitting device according to claim 11, wherein the chemical formula 3 is represented by any one of the following compounds: .
An organic light-emitting device according to claim 11, wherein the weight ratio of the compound represented by Formula 1 and the compound represented by Formula 2 is 1:1 to 1:10, or the weight ratio of the compound represented by Formula 1 and the compound represented by Formula 3 is 1:1 to 1:10.
A composition for an organic layer of an organic light-emitting device comprising: a heterocyclic compound represented by Formula 1 according to any one of claims 1 to 7; and a heterocyclic compound represented by Formula 2 or Formula 3 below: [Chemical Formula 2] In Chemical Formula 2, R21 and R22 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R7 and R8 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; 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, and r7 and r8 are each integers from 0 to 7, and if r7 is 2 or more, R7 are the same or different from each other, and if r8 is 2 or more, R8 are the same or different from each other, and [Chemical Formula 3] In Chemical Formula 3, A is a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, and R23 and R24 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R9 and R10 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; 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, and r9 and r10 are each integers from 0 to 4, and if r9 is 2 or more, R9 are the same or different from each other, and if r10 is 2 or more, R10 are the same or different from each other.
A composition for an organic layer of an organic light-emitting device according to claim 15, wherein the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 in the composition for the organic layer of the organic light-emitting device is 1:1 to 1:10, or the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 3 is 1:1 to 1:10.

Description

Heterocyclic compound, organic light-emitting device comprising the same, and composition for organic material layer of organic light-emitting device The present invention relates to a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer of an organic light-emitting device. The present application claims the benefit of the filing dates of Korean Patent Application No. 10-2024-0148376 filed with the Korean Intellectual Property Office on October 28, 2024 and Korean Patent Application No. 10-2024-0190780 filed with the Korean Intellectual Property Office on December 19, 2024, the entire contents of which are incorporated herein by reference. Electroluminescent devices are a type of self-emissive display device that has the advantages of a wide viewing angle, excellent contrast, and fast response speed. An organic light-emitting diode has a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting diode with such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs and then annihilate, emitting light. The organic thin film can be composed of a single layer or multiple layers as needed. The materials of organic thin films may possess luminescence capabilities as needed. For example, compounds capable of independently constituting an emissive layer may be used as organic thin film materials, or compounds capable of acting as a host or dopant in a host-dopant emissive layer may be used. In addition, compounds capable of performing functions such as hole injection, hole transport, electron blocking, and electron injection may also be used as organic thin film materials. To improve the performance, efficiency, and lifespan of organic light-emitting diodes, the development of organic thin film materials is continuously required. FIGS. 1 to 3 are schematic diagrams illustrating the stacked structure of an organic light-emitting device according to one embodiment of the present application. The present specification will be described in more detail below. In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components. In this specification, of the chemical formula means the position where it is combined. In this specification, n of Cn means the number of carbon atoms. That is, for example, C6 to C60 means 6 to 60 carbon atoms. In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution location is not limited to the location where the hydrogen atom is substituted, that is, any location where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other. In this specification, "substituted or unsubstituted" means deuterium; halogen group; -CN; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; C6 to C60 aryloxy group; C1 to C60 alkylthioxy group; C6 to C60 arylthioxy group; C1 to C60 alkyl sulfoxy group; C6 to C60 aryl sulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; It means that one or more substituents selected from the group consisting of -SiRR'R"; -P(=O)RR'; and -NRR' are substituted or unsubstituted with a substituent connected to two or more substituents selected from the above substituents, and R, R' and R" are each independently substituents consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group. In this specification, "where no substituent is indicated in the chemical formula or compound structure" means that hydrogen atoms are bonded to carbon atoms. However, since deuterium ( 2H ) is an isotope of hydrogen, some hydrogen atoms may be deuterium. In one embodiment of the present application, "where no substituents are indicated in the chemical formula or compound structure" may mean that all positions where substituents may be present are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium isotopes, and in this case, the content of deuterium may be 0% to 100%. In one embodiment of the present application, where "substituents are not indicated in the chemical formula or compound structure," if the deuterium content is 0%, the hydrogen content is 100%, and all substituents do not explicitly exclude hydrogen or other deuterium, hydrogen and deuterium may be used in a mixture in the compound. In one embodiment of the present ap