KR-20260065657-A - COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

KR20260065657AKR 20260065657 AKR20260065657 AKR 20260065657AKR-20260065657-A

Abstract

The present specification relates to a compound of Formula 1 and an organic light-emitting device containing the same.

Inventors

이성재
김민준
문현진
전현수
홍성길

Assignees

주식회사 엘지화학

Dates

Publication Date: 20260511
Application Date: 20241101

Claims (10)

Compound of Chemical Formula 1 below: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, One or more of A1 to A5 is the above chemical formula 2, and A1 to A5 other than the above chemical formula 2 are the same or different from one another and each independently are hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms comprising one or more heteroatoms among N, O, and S, or adjacent substituents may bond to each other to form a substituted or unsubstituted ring, and n3 is an integer from 1 to 5, and n1, n2, n4, and n5 are integers from 1 to 4, respectively, and If n1 to n5 are each 2 or greater, the substituents inside the parentheses are the same or different from each other, and In the above chemical formula 2, L1 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted quaternphenylene group; a substituted or unsubstituted polycyclic arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms comprising one or more heteroatoms among N, O, and S, and L and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms comprising one or more heteroatoms among N, O and S, and Ar1 is a condensed ring comprising a substituted or unsubstituted cycloalkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted monocyclic aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted polycyclic aryl group having two or three rings; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms comprising one or more heteroatoms among N, O, and S, or a substituted or unsubstituted cycloalkyl group having 1 to 60 carbon atoms combined with a substituted or unsubstituted monocyclic aryl group having 6 to 60 carbon atoms. R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms comprising one or more heteroatoms among N, O, and S. a is an integer from 1 to 3, and b is an integer from 1 to 8, and If a and b are each 2 or more, the substituents inside the parentheses are the same or different.
A compound according to claim 1, wherein the chemical formula 1 is the following chemical formula 1-A: [Chemical Formula 1-A] In the above chemical formula 1-A, n1, n4, and n5 are as defined in Chemical Formula 1 above, and One or more of A1 to A5 is the above chemical formula 2, and A1 to A5 other than the above chemical formula 2 are the same or different from one another and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms comprising one or more heteroatoms among N, O, and S. n2 is an integer from 1 to 3, and n3 is an integer from 1 to 4, and If n2 and n3 are each 2 or greater, the substituents inside the parentheses are the same or different.
In claim 1, The above chemical formula 2 is a compound having the following chemical formula 2-A or 2-B: [Chemical Formula 2-A] [Chemical Formula 2-B] In the above chemical formulas 2-A and 2-B, L, L1, L2, Ar1, a, and b are as defined in Chemical Formula 2 above, and R11 and R21 are the same or different from each other and are each independently hydrogen; or deuterium, and b' is an integer from 1 to 4, and The substituent sites that can be replaced with hydrogen can be replaced with deuterium.
In claim 1, A compound in which the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In the above chemical formulas 1-1 to 1-3, n1 to n5 are as defined in Chemical Formula 1 above, and L, L2, Ar1, R1, R2, a and b are as defined in Chemical Formula 2 above, and A1 to A5 are the same or different from one another and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms comprising one or more heteroatoms among N, O, and S, or adjacent substituents may bond to each other to form a substituted or unsubstituted ring, and L1 is a direct bond; a phenylene group substituted or unsubstituted with deuterium; a terphenylene group substituted or unsubstituted with deuterium; a quaternarylene group substituted or unsubstituted with deuterium; a polycyclic arylene group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; or a heteroarylene group having 2 to 30 carbon atoms substituted or unsubstituted with a deuterium or alkyl group comprising one or more heteroatoms among N, O and S.
In claim 1, A compound wherein the above Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted tetrahydronaphthalene group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted adamanthen group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
In claim 1, The above L1 is a compound in which the direct bond; or a phenylene group substituted or unsubstituted with a deuterium, halogen group, nitrile group, silyl group, or alkyl group.
A compound according to claim 1, wherein the chemical formula 1 is any one of the following compounds: .
A compound according to claim 1, wherein the chemical formula 1 is any one of the following compounds: In the above structural formula, n is the number of deuterium atoms substituted at substitutable positions in the compound inside the parentheses, and In this case, n is an integer greater than or equal to 1.
An organic light-emitting device comprising: a first electrode; a second 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 compound according to any one of claims 1 to 8.
An organic light-emitting device according to claim 9, wherein the organic layer comprises a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer comprises the compound.

Description

Compound and Organic Light Emitting Device Comprising the Same This specification relates to a compound and an organic light-emitting device containing the same. In this specification, an organic light-emitting device refers to a light-emitting device utilizing an organic semiconductor material, which requires the exchange of holes and/or electrons between an electrode and an organic semiconductor material. Organic light-emitting devices can be broadly classified into two types based on their operating principles as follows. The first is a light-emitting device in which excitons are formed in an organic layer by photons introduced into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are each transferred to different electrodes to be used as current sources (voltage sources). The second is a light-emitting device in which holes and/or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes by applying voltage or current to two or more electrodes, and the device operates based on the injected electrons and holes. Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron blocking layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state. Such OLEDs are known to possess characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, a wide viewing angle, and high contrast. Materials used as organic layers in organic light-emitting diodes can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron blocking materials, electron transport materials, and electron injection materials. Light-emitting materials are classified according to their emission color into blue, green, and red light-emitting materials, as well as yellow and orange light-emitting materials necessary to achieve better natural colors. In addition, a host/dopant system can be used as a light-emitting material to increase color purity and luminous efficiency through energy transfer. The principle is that when a small amount of a dopant, which has a smaller energy band gap and superior luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated from the host are transported to the dopant to emit high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength range of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used. In order to fully exhibit the excellent characteristics of the aforementioned organic light-emitting diode, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron blocking materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials, so the development of new materials is continuously required. Figure 1 illustrates an example of an organic light-emitting device according to the present invention. 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, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members. The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site 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, the term “substitu