KR-20260065843-A - Organic compounds and organic light-emitting diodes containing the same

Abstract

The present invention is intended to provide a novel organic compound and an organic light-emitting device comprising the same. An organic light-emitting device comprising a compound represented by Formula 1 of the present invention has excellent characteristics such as driving voltage, luminous efficiency, external quantum efficiency (EQE), long lifespan, and stability.

Inventors

• 송걸
• 신기훈
• 양희진
• 이기림
• 조우형
• 김승현
• 박희준

Assignees

• 머티어리얼사이언스 주식회사

Dates

Publication Date

20260511

Application Date

20250110

Priority Date

20240112

Claims (5)

1. Organic compound represented by the following chemical formula 1: [Chemical Formula 1] X is oxygen (O) or sulfur (S), and Y1 , Y2 , and Y3 are nitrogen (N) or CR2 , and At least two of Y1 , Y2 , and Y3 are nitrogen (N), and Z1 , Z2 , and Z3 are nitrogen (N) or CR3 , and L1 and L2 are identical or different from each other and are each independently selected from the group consisting of a directly bonded, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylene group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms, and a substituted or unsubstituted heteroarylalkylene group having 6 to 60 carbon atoms. A is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can combine with adjacent groups to form a substituted or unsubstituted ring. Ar 1 and Ar 2 are identical or different from each other and are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can combine with adjacent groups to form a substituted or unsubstituted ring. R1 , R2, and R3 are identical or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can combine with adjacent groups to form a substituted or unsubstituted ring. p is an integer from 0 to 7, and The substituents of L1 , L2 , A, Ar1, Ar2 , R1 , R2 , and R3 are each independently deuterium, trifluoromethyl group, nitro group, halogen group, hydroxyl group, trimethylsilyl group (TMS), alkyl group having 1 to 30 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, alkenyl group having 2 to 30 carbon atoms, cycloalkenyl group having 3 to 20 carbon atoms, alkynyl group having 2 to 30 carbon atoms, cycloalkynyl group having 3 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, heteroaryl group having 5 to 60 carbon atoms, heteroarylalkyl group having 6 to 60 carbon atoms, amine group, alkylamino group having 1 to 30 carbon atoms, and alkylamino group having 7 to 30 carbon atoms. It is substituted with one or more substituents selected from the group consisting of an arylalkylamino group, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 5 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms. When substituted with multiple substituents, these may be identical or different from each other and may combine with adjacent groups to form a substituted or unsubstituted ring.
2. In paragraph 1, An organic compound wherein the above chemical formula 1 is represented by one of the following chemical formulas 2 to 4. [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 2 to 4, X, L1 , L2 , A, Ar1 , Ar2 , R1 and p and their substituents are as defined in Chemical Formula 1 above.
3. First electrode; A second electrode facing the first electrode; and One or more organic layers are included between the first electrode and the second electrode, and An organic light-emitting diode, wherein at least one of the above organic layers comprises an organic compound according to claim 1.
4. In paragraph 3, An organic light-emitting diode, wherein the organic layer comprising the organic compound according to claim 1 above is an electron transport assisting layer or an electron transport layer.
5. In paragraph 4, The organic light-emitting device, wherein the above organic layer further comprises one or more selected from a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection layer.

Description

Organic compounds and organic light-emitting diodes containing the same Organic compounds and organic light-emitting diodes containing the same The present invention relates to an organic compound and an organic light-emitting diode containing the same. Organic light-emitting diodes (OLEDs) have a simpler structure and various advantages in manufacturing processes compared to other flat-panel display devices such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs). They also feature excellent high brightness and viewing angle characteristics, fast response speeds, and low driving voltages, leading to active development and commercialization for use in flat-panel displays such as wall-mounted TVs, as well as as light sources for backlighting, lighting, and advertising boards. An organic light-emitting diode consists of an organic layer between two electrodes. It is a device that utilizes the principle in which electrons and holes are injected into the light-emitting layer from the two electrodes, respectively, to generate excitons through the combination of electrons and holes, and light is emitted when the generated excitons fall from the excited state to the ground state. An organic light-emitting device may include at least one light-emitting layer. Generally, an organic light-emitting device having a plurality of light-emitting layers may include light-emitting layers that emit light having different peak wavelengths, and may realize a specific color through a combination of light having different peak wavelengths. These organic light-emitting diodes can be classified into front-emitting and back-emitting diode structures. Front-emitting diodes utilize a reflective cathode to emit light generated in the emissive layer toward a translucent anode. In contrast, back-emitting diodes utilize a reflective anode to emit light generated in the emissive layer, reflected from the anode, toward a transparent cathode in the direction of the driving thin-film transistor. Meanwhile, the most critical issues regarding organic light-emitting diodes (OLEDs) are lifespan and efficiency; as displays become larger in size, these efficiency and lifespan issues must be resolved. In OLEDs, the characteristics of the components contained in each layer of the organic film layer—which consists of one or multiple layers including a light-emitting layer between the anode and cathode—affect the device's driving voltage, luminous efficiency, and brightness. Consequently, these characteristics have a significant impact on the device's lifespan. Therefore, research on the components included in each layer of the aforementioned organic film layer is actively underway. The aforementioned objectives, features, and advantages are described in detail below, and accordingly, a person skilled in the art to which the present invention pertains will be able to easily implement the technical concept of the present invention. In describing this specification, if it is determined that a detailed description of related prior art could unnecessarily obscure the gist of this specification, such detailed description is omitted. In this specification, where terms such as “comprising,” “having,” “consisting of,” “arranging,” or “having” are used for a component, other parts may be added unless “only” is used. Where a component is expressed in the singular, it includes cases where it is included in the plural unless specifically stated otherwise. In interpreting the components in this specification, they are interpreted to include an error range even if there is no separate explicit description. In this specification, the statement that any configuration is disposed on the “upper (or lower) side” of a component or on the “upper (or lower) side” of a component may mean not only that any configuration is disposed in contact with the upper (or lower) surface of said component, but also that another configuration may be interposed between said component and any configuration disposed on (or below) said component. The term “halogen group” as used in this specification includes fluorine, chlorine, bromine, and iodine. As used herein, the term “alkyl group” refers to both straight-chain alkyl radicals and branched-chain alkyl radicals. Unless otherwise specified, the alkyl group contains 1 to 30 carbon atoms and may include, but is not limited to, methyl, ethyl, propyl, isopropyl, butyl, secondary butyl, isobutyl, ter-butyl, pentyl, isoamyl, hexyl, etc. Additionally, the alkyl group may be optionally substituted. As used herein, the term “cycloalkyl group” means a cyclic alkyl radical. Unless otherwise specified, the cycloalkyl group comprises 3 to 20 carbon atoms and may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, etc. Additionally, the cycloalkyl group may be optionally substituted. As used herein, the term “alkenyl group” refers to both straight-chai