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KR-20260068031-A - ORGANIC ELECTROLUMINESCENCE DEVICE AND AMINE COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE

KR20260068031AKR 20260068031 AKR20260068031 AKR 20260068031AKR-20260068031-A

Abstract

An organic electroluminescent device of one embodiment comprises a first electrode, a second electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, and any one of the plurality of organic layers comprises an amine compound represented by Formula 1, which can exhibit excellent luminescence efficiency and improved lifetime characteristics.

Inventors

  • 이마이즈미 타쿠

Assignees

  • 삼성디스플레이 주식회사

Dates

Publication Date
20260513
Application Date
20260417

Claims (11)

  1. First electrode; A second electrode facing the first electrode; and A plurality of organic layers disposed between the first electrode and the second electrode; comprising, An organic electroluminescent device comprising one of the plurality of organic layers, wherein the organic layer comprises an amine compound represented by any one of the following chemical formulas 3-2 and 3-3: [Chemical Formula 3-2] [Chemical Formula 3-3] In the above chemical formulas 3-2 and 3-3, R1 and R2 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, and X is O or S, and R3 and R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, provided that when R3 and R4 are each heteroaryl groups, the carbazole group is excluded. L is a direct linkage, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 2 to 30 carbon atoms, and m is an integer between 0 and 4 inclusive, and Y is O or S, and at least one of X and Y is O, and R5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, provided that when R5 is a heteroaryl group, the carbazole group is excluded, and n is an integer between 0 and 4 inclusive, and The above amine compound is a monoamine compound.
  2. In Article 1, An organic electroluminescent device in which L is a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.
  3. In Article 1, The above R 4 and R 5 are each independently an organic electroluminescent device that is a hydrogen atom, a deuterium atom, or a phenyl group.
  4. In Article 1, The above amine compound is an organic electroluminescent device represented by any one of the following chemical formulas 4-1, 4-3 to 4-5, 4-8, and 4-9: [Chemical Formula 4-1] [Chemical Formula 4-3] [Chemical Formula 4-4] [Chemical Formula 4-5] [Chemical Formula 4-8] [Chemical Formula 4-9] In the above formulas 4-1, 4-3 to 4-5, 4-8, and 4-9, The above R 1 to R 5 , L, m, and n are as defined in Chemical Formula 3-2 and Chemical Formula 3-3.
  5. In Article 1, The above plurality of organic layers include a hole transport region, a light-emitting layer, and an electron transport region, and The hole transport region above is an organic electroluminescent device comprising the amine compound above.
  6. In Article 5, The above hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer, and The hole transport layer above is an organic electroluminescent device comprising the amine compound.
  7. First electrode; A second electrode facing the first electrode; and A plurality of organic layers disposed between the first electrode and the second electrode; comprising, Any one of the plurality of organic layers comprises an amine compound, and the amine compound is one of the compounds indicated in compound groups A to F below, including A46, A47, A49 to A53, A61, A62, A66, A70, A72, A74, A76, A78, A79, A81, A83, A84, A86, A89, A90, C1, C2, C4 to C8, C11, C14, C16, C17, C21, C25, C27, C29, C31, C33, C34, C36, C38, C39, C41, D1, D2, D4 to D8, D11, D14, D16, D17, D21, D25, D27, D29, D31, D33, D34, D36, D38, Organic electroluminescent device that is any one of the compounds excluding D39 and D41: [Compound Group A] [Compound Group B] [Compound Group C] [Compound Group D] [Compound Group E] [Compound Group F] .
  8. An amine compound represented by either of the following chemical formulas 3-2 and 3-3: [Chemical Formula 3-2] [Chemical Formula 3-3] In the above chemical formulas 3-2 and 3-3, R1 and R2 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, and X is O or S, and R3 and R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, provided that the carbazole group is excluded from the heteroaryl group, L is a direct linkage, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 2 to 30 carbon atoms, and m is an integer between 0 and 4 inclusive, and Y is O or S, and at least one of X and Y is O, and R5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, provided that the carbazole group is excluded from the heteroaryl group, n is an integer between 0 and 4 inclusive, and The above amine compound is a monoamine compound.
  9. In Article 8, The above L is an amine compound in which the above L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted arylene group having 2 to 30 carbon atoms.
  10. In Article 8, The above amine compound is an amine compound represented by any one of the following formulas 4-1, 4-3 to 4-5, 4-8, and 4-9: [Chemical Formula 4-1] [Chemical Formula 4-3] [Chemical Formula 4-4] [Chemical Formula 4-5] [Chemical Formula 4-8] [Chemical Formula 4-9] In the above formulas 4-1, 4-3 to 4-5, 4-8, and 4-9, The above R 1 to R 5 , L, m, and n are as defined in Chemical Formula 3-2 and Chemical Formula 3-3.
  11. An amine compound represented by any one of the compounds listed in compound groups A to F below, excluding A46, A47, A49 to A53, A61, A62, A66, A70, A72, A74, A76, A78, A79, A81, A83, A84, A86, A89, A90, C1, C2, C4 to C8, C11, C14, C16, C17, C21, C25, C27, C29, C31, C33, C34, C36, C38, C39, C41, D1, D2, D4 to D8, D11, D14, D16, D17, D21, D25, D27, D29, D31, D33, D34, D36, D38, D39, and D41: [Compound Group A] [Compound Group B] [Compound Group C] [Compound Group D] [Compound Group E] [Compound Group F] .

Description

Organic Electroluminescent Device and Amine Compound for Organic Electroluminescent Device The present invention relates to an organic electroluminescent device and an amine compound used therein. Recently, there has been active development of organic electroluminescence displays as image display devices. An organic electroluminescence display is a so-called self-emissive display device that generates excitons by recombining holes and electrons injected from a first electrode and a second electrode in a light-emitting layer, and realizes display by generating light by dropping the generated excitons to a ground state. In applying organic light-emitting diodes to display devices, there is a demand for lower driving voltage, higher luminous efficiency, and longer lifespan of the devices, and there is a continuous need for the development of materials for organic light-emitting diodes that can stably realize these requirements. Meanwhile, while the development of amine compounds continues in the development of materials for hole transport, there is a demand for the development of amine compounds with high efficiency and long lifespan, as well as organic electroluminescent devices containing them. FIG. 1 is a schematic cross-sectional view of an organic electroluminescent device according to one embodiment of the present invention. FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. FIG. 4 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. The present invention is capable of various modifications and may take various forms, and specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the invention to the specific disclosed forms, and it should be understood that the invention includes all modifications, equivalents, and substitutions that fall within the spirit and scope of the invention. In this specification, where a component (or region, layer, part, etc.) is described as being "on," "connected," or "combined" with another component, it means that it may be directly placed/connected/combined with the other component, or that a third component may be placed between them. Identical reference numerals denote identical components. Additionally, in the drawings, the thicknesses, proportions, and dimensions of the components are exaggerated for the effective illustration of the technical content. "And/or" includes all one or more combinations that the associated configurations can define. Terms such as "first," "second," etc., may be used to describe various components, but said components should not be limited by said terms. These terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be named the second component, and similarly, the second component may be named the first component. A singular expression includes a plural expression unless the context clearly indicates otherwise. Additionally, terms such as "below," "lower side," "above," and "upper side" are used to describe the relationships between the components depicted in the drawings. These terms are relative concepts and are described based on the directions indicated in the drawings. Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as generally understood by those skilled in the art to which the present invention pertains. Additionally, terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the relevant technology, and are explicitly defined herein unless interpreted in an ideal or overly formal sense. Terms such as "include" or "have" are intended to indicate the existence of the features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, and should be understood as not precluding the existence or addition of one or more other features, numbers, steps, actions, components, parts, or combinations thereof. Hereinafter, an organic electroluminescent device according to one embodiment of the present invention and an amine compound of one embodiment included therein will be described with reference to the drawings. FIGS. 1 to 4 are cross-sectional views schematically illustrating an organic electroluminescent device according to an embodiment of the present invention. Referring to FIGS. 1 to 4, in an organic electroluminescent device (10) of an embodiment, a first electrode (EL1) and a second electrode (EL2) are arranged facing each other,