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KR-20260062866-A - HETEROCYCLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE AND COMPOSITION FOR ORGANIC MATERIAL LAYER OF ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME

KR20260062866AKR 20260062866 AKR20260062866 AKR 20260062866AKR-20260062866-A

Abstract

This specification relates to heterocyclic compounds and organic light-emitting devices containing the same.

Inventors

  • 최의정
  • 이현주
  • 노영석
  • 김동준
  • 최대혁

Assignees

  • 엘티소재주식회사

Dates

Publication Date
20260507
Application Date
20251027
Priority Date
20241028

Claims (14)

  1. Heterocyclic compounds represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is O; S; or CRaRb; and, L is a directly bonded; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and l is an integer from 1 to 3, and if l is 2 or greater, L are equal to or different from each other, and A is an aryl ring having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic ring having 2 to 60 carbon atoms substituted or unsubstituted with deuterium, and Ra, Rb, Rd, Ar1 and Ar2 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and a is an integer from 0 to 4, and if a is 2 or greater, Rd are equal or different, and H is hydrogen, D is deuterium, and, d is an integer from 1 to 6, and The above chemical formula 1 is represented by the following structural formulas A to C, and [Structural Formula A] [Structural Formula B] [Structural Formula C] In the above structural formulas A to C, refers to the positions where they combine with each other, The deuterium content of the above structural formula B is 50% or more and 90% or less.
  2. A heterocyclic compound according to claim 1, wherein the deuterium content of structural formula A is 10% or less and the deuterium content of structural formula C is 10% or less.
  3. In claim 1, A heterocyclic compound wherein at least one of the above Ar1 and Ar2 is a substituted or unsubstituted aryl group having 10 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  4. Claim 1, wherein A is a heterocyclic compound represented by the following structural formula A-1 or A-2: [Structural Formula A-1] [Structural Formula A-2] In the above structural formulas A-1 and A-2, represents the condensation location, X3 is O; S; or NRe, and R11 to R19 are the same or different from each other and are each independently hydrogen; or deuterium, and Re is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and The above a1 is an integer of 1 or 2, and If a1 is 2, the substituents inside the parentheses are either the same or different.
  5. A heterocyclic compound according to claim 1, wherein Ar1 and Ar2 are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms comprising O or S.
  6. A heterocyclic compound according to claim 1, wherein the deuterium substitution rate of the compound of formula 1 is 10% or more and 60% or less.
  7. In claim 1, The above chemical formula 1 is a heterocyclic compound represented by any one of the following compounds:
  8. 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.
  9. 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.
  10. 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.
  11. 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: [Chemical Formula 2] In the above chemical formula 2, R1 to R9 are the same or different from one another and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; substituted or unsubstituted phosphine oxide group; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups are combined to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms, d is an integer from 0 to 2, and when d is an integer of 2, R9 are the same or different from each other, and L1 and L2 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; and Ar3 and Ar4 are the same or different from each other and each independently are deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and m and n are integers from 0 to 4, and p and q are integers from 1 to 6, and If m, n, p, and q are 2 or more, the substituents within the parentheses are the same or different from each other, and The deuterium content of the above chemical formula 2 is 30% or less.
  12. An organic light-emitting device according to claim 11, wherein the chemical formula 2 is represented by any one of the following compounds:
  13. 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 below: [Chemical Formula 2] In the above chemical formula 2, R1 to R9 are the same or different from one another and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; substituted or unsubstituted phosphine oxide group; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups are combined to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms, d is an integer from 0 to 2, and when d is an integer of 2, R9 are the same or different from each other, and L1 and L2 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; and Ar3 and Ar4 are the same or different from each other and each independently are deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and m and n are integers from 0 to 4, and p and q are integers from 1 to 6, and If m, n, p, and q are 2 or more, the substituents within the parentheses are the same or different from each other, and The deuterium content of the above chemical formula 2 is 30% or less.
  14. In claim 13, A composition for an organic layer of an organic light-emitting device, wherein the weight ratio of the heterocyclic compound represented by Chemical Formula 2 in the composition is higher than the weight ratio of the heterocyclic compound represented by Chemical Formula 1.

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. 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', or two or more substituents selected from the examples above are connected to a substituent, 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 one embodiment of the present application, deuterium is one of the isotopes of hydrogen and is an element having a deuteron, consisting of one proton and one neutron, as its nucleus, which can be represented as hydrogen-2, and its element symbol may be written as D or 2 H. In one embodiment of the present application, an isotope, which means an atom having the same atomic number (Z) but different mass number (A), can also be interpreted as an element having the same number of protons but different number of neutrons. In one embodiment of the present application, the meaning of the content T% of a specific substituent can be defined as T2/T1Y100 = T% when the total number of substituents that a basic compound may have is defined as T1 and the number of specific substituents among them is defined as T2. That is, in one example, A deuterium content of 20% in a phenyl group represented by can be expressed as 20% when the total number of substituents that the phenyl group can have is 5 (T1 in the formula) and the number of deuteriums among them is 1 (T2 in the formula). That is, a deuterium content of 20% in a phenyl group can be represented by the following structural formula. In addition, in one embodiment of the present application, "phenyl group having 0% deuterium content" may mean a phenyl group that does not contain deuterium atoms, i.e., has five hydrogen atoms. In this specification, the halogen may